IL44587A - 1-phenyl-1,7-alkadiene derivatives - Google Patents

1-phenyl-1,7-alkadiene derivatives

Info

Publication number: IL44587A
Authority: IL; Israel
Prior art keywords: compound; formula; reacting; preparing; reaction
Prior art date: 1973-04-27

Application number

IL44587A

Other languages

English (en)

Other versions

IL44587A0 (en

Original Assignee

Lilly Co Eli

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-04-27

Filing date

1974-04-09

Publication date

1977-06-30

1974-04-09 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1974-06-30 Publication of IL44587A0 publication Critical patent/IL44587A0/xx

1977-06-30 Publication of IL44587A publication Critical patent/IL44587A/en

Links

RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 40
150000001875 compounds Chemical class 0.000 claims description 24
238000000034 method Methods 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
239000003208 petroleum Substances 0.000 claims description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
229910000104 sodium hydride Inorganic materials 0.000 claims description 5
239000012312 sodium hydride Substances 0.000 claims description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 4
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
150000003333 secondary alcohols Chemical class 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
241000238631 Hexapoda Species 0.000 description 11
-1 halo compound Chemical class 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
238000005481 NMR spectroscopy Methods 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000002949 juvenile hormone Substances 0.000 description 5
229930014550 juvenile hormone Natural products 0.000 description 5
150000003633 juvenile hormone derivatives Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000002689 soil Substances 0.000 description 5
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
238000003747 Grignard reaction Methods 0.000 description 4
NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 4
QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000000366 juvenile effect Effects 0.000 description 4
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
FCYRGFFVNYSYSK-UHFFFAOYSA-N 5-(4,8-dimethylnona-1,7-dienyl)-1,3-benzodioxole Chemical compound CC(C)=CCCC(C)CC=CC1=CC=C2OCOC2=C1 FCYRGFFVNYSYSK-UHFFFAOYSA-N 0.000 description 3
QPKCDMXLSDFCQD-UHFFFAOYSA-N 8-bromo-2,6-dimethyloct-2-ene Chemical compound BrCCC(C)CCC=C(C)C QPKCDMXLSDFCQD-UHFFFAOYSA-N 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
241000462639 Epilachna varivestis Species 0.000 description 3
241000258913 Oncopeltus fasciatus Species 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
230000003054 hormonal effect Effects 0.000 description 3
239000012433 hydrogen halide Substances 0.000 description 3
229910000039 hydrogen halide Inorganic materials 0.000 description 3
239000010410 layer Substances 0.000 description 3
JZOMOBUGVZDCPA-UHFFFAOYSA-N nona-2,6-diene Chemical class CCC=CCCC=CC JZOMOBUGVZDCPA-UHFFFAOYSA-N 0.000 description 3
IPNPIHIZVLFAFP-UHFFFAOYSA-N phosphorus tribromide Chemical compound BrP(Br)Br IPNPIHIZVLFAFP-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
POZQPLMVTQPOTQ-GQCTYLIASA-N (7e)-nona-1,7-diene Chemical compound C\C=C\CCCCC=C POZQPLMVTQPOTQ-GQCTYLIASA-N 0.000 description 2
QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LZBXPXAOYQVZEC-RIYZIHGNSA-N Dendrolasin Chemical compound CC(C)=CCC\C(C)=C\CCC=1C=COC=1 LZBXPXAOYQVZEC-RIYZIHGNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
241000254105 Tenebrio Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
OGBVRMYSNSKIEF-UHFFFAOYSA-L benzyl-dioxido-oxo-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-L 0.000 description 2
JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229930003633 citronellal Natural products 0.000 description 2
235000000983 citronellal Nutrition 0.000 description 2
235000000484 citronellol Nutrition 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000012024 dehydrating agents‎ Substances 0.000 description 2
230000018044 dehydration Effects 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
LZBXPXAOYQVZEC-UHFFFAOYSA-N dendrolasin Natural products CC(C)=CCCC(C)=CCCC=1C=COC=1 LZBXPXAOYQVZEC-UHFFFAOYSA-N 0.000 description 2
230000026030 halogenation Effects 0.000 description 2
238000005658 halogenation reaction Methods 0.000 description 2
239000005556 hormone Substances 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000001418 larval effect Effects 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
POZQPLMVTQPOTQ-UHFFFAOYSA-N nona-1,7-diene Chemical class CC=CCCCCC=C POZQPLMVTQPOTQ-UHFFFAOYSA-N 0.000 description 2
229940081310 piperonal Drugs 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HNYSEGRXBCSMMF-UHFFFAOYSA-N 1-(4,8-dimethylnona-3,7-dienyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CCC=C(C)CCC=C(C)C)=C1 HNYSEGRXBCSMMF-UHFFFAOYSA-N 0.000 description 1
PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
GUNIRFUVZXJDNQ-UHFFFAOYSA-N 2-(4,8-dimethylnona-3,7-dienyl)furan Chemical compound CC(C)=CCCC(C)=CCCC1=CC=CO1 GUNIRFUVZXJDNQ-UHFFFAOYSA-N 0.000 description 1
JWOCBWGOMKNXHV-UHFFFAOYSA-N 5-(4,8-dimethylnona-3,7-dienyl)-1,3-benzodioxole Chemical compound CC(C)=CCCC(C)=CCCC1=CC=C2OCOC2=C1 JWOCBWGOMKNXHV-UHFFFAOYSA-N 0.000 description 1
DWSUJONSJJTODA-UHFFFAOYSA-N 5-(chloromethyl)-1,3-benzodioxole Chemical compound ClCC1=CC=C2OCOC2=C1 DWSUJONSJJTODA-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
238000004566 IR spectroscopy Methods 0.000 description 1
238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
241000254109 Tenebrio molitor Species 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229930004069 diterpene Natural products 0.000 description 1
150000004141 diterpene derivatives Chemical class 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
229930191400 juvenile hormones Natural products 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
229910001623 magnesium bromide Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000035800 maturation Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
230000002688 persistence Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940001593 sodium carbonate Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Furan Compounds (AREA)

IL44587A 1973-04-27 1974-04-09 1-phenyl-1,7-alkadiene derivatives IL44587A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US354970A US3923832A (en)	1973-04-27	1973-04-27	Insecticidal substituted alkenes

Publications (2)

Publication Number	Publication Date
IL44587A0 IL44587A0 (en)	1974-06-30
IL44587A true IL44587A (en)	1977-06-30

Family

ID=23395678

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL44587A IL44587A (en)	1973-04-27	1974-04-09	1-phenyl-1,7-alkadiene derivatives

Country Status (12)

Country	Link
US (1)	US3923832A (fr)
JP (1)	JPS5013336A (fr)
BE (1)	BE814141A (fr)
CA (1)	CA1018178A (fr)
CH (1)	CH603620A5 (fr)
DE (1)	DE2419823A1 (fr)
FR (1)	FR2227250B1 (fr)
GB (1)	GB1474937A (fr)
IE (1)	IE39118B1 (fr)
IL (1)	IL44587A (fr)
IT (1)	IT1049226B (fr)
NL (1)	NL7405545A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4803290A (en) *	1987-05-29	1989-02-07	Pcri, Inc.	Nonanol/nonene antimicrobial compositions

1973
- 1973-04-27 US US354970A patent/US3923832A/en not_active Expired - Lifetime
1974
- 1974-04-05 IE IE00741/74A patent/IE39118B1/xx unknown
- 1974-04-09 IL IL44587A patent/IL44587A/en unknown
- 1974-04-10 CA CA197,314A patent/CA1018178A/fr not_active Expired
- 1974-04-23 GB GB1777874A patent/GB1474937A/en not_active Expired
- 1974-04-24 DE DE2419823A patent/DE2419823A1/de active Pending
- 1974-04-24 NL NL7405545A patent/NL7405545A/xx not_active Application Discontinuation
- 1974-04-25 BE BE1005906A patent/BE814141A/fr unknown
- 1974-04-26 CH CH578074A patent/CH603620A5/xx not_active IP Right Cessation
- 1974-04-26 IT IT21951/74A patent/IT1049226B/it active
- 1974-04-26 JP JP49047482A patent/JPS5013336A/ja active Pending
- 1974-04-26 FR FR7414685A patent/FR2227250B1/fr not_active Expired

Also Published As

Publication number	Publication date
FR2227250A1 (fr)	1974-11-22
FR2227250B1 (fr)	1979-05-11
GB1474937A (en)	1977-05-25
IT1049226B (it)	1981-01-20
DE2419823A1 (de)	1974-11-21
IE39118B1 (en)	1978-08-02
NL7405545A (fr)	1974-10-29
US3923832A (en)	1975-12-02
IE39118L (en)	1974-10-27
IL44587A0 (en)	1974-06-30
CA1018178A (fr)	1977-09-27
BE814141A (fr)	1974-10-25
CH603620A5 (fr)	1978-08-31
JPS5013336A (fr)	1975-02-12

Publication	Publication Date	Title
RU2099325C1 (ru)	1997-12-20	СПОСОБ ПОЛУЧЕНИЯ ЭФИРОВ 13,14-ДИГИДРО-15(R)-17-ФЕНИЛ-18,19,20-ТРИНОР PGF2α 13,14-ДИГИДРО-15(R)-17-ФЕНИЛ-18,19,20-ТРИНОР PGF2α СОЕДИНЕНИЯ.
US4116979A (en)	1978-09-26	Process for the preparation of (-)-6a,10a-trans-6a,7,8,10a-tetrahydrodibenzo[b,d]-pyrans
US4571428A (en)	1986-02-18	6-Substituted-4-hydroxy-tetrahydropyran-2-ones
Ohwa et al.	1986	An asymmetric synthesis of enantiomerically pure (S)-(+)-linalool (3, 7-dimethyl-1, 6-octadien-3-ol) and a formal synthesis of (R)-(-)-linalool
HU206302B (en)	1992-10-28	Process for producing hydroxyl-protected /7e,9z/-7,9-alkadien-1-ols and derivatives
CA1258863A (fr)	1989-08-29	Derives de cyclohexane
US5986113A (en)	1999-11-16	Process for manufacturing polyene esters and acids
HU185330B (en)	1985-01-28	Process for preparing /+/-4-substituted-2-indazoles
US5130472A (en)	1992-07-14	Total synthesis of erbstatin analogs
US4803301A (en)	1989-02-07	Process for producing optically active 2-phenoxypropionic acid
US3923832A (en)	1975-12-02	Insecticidal substituted alkenes
US4107181A (en)	1978-08-15	Useful prostaglandin intermediates
US4170596A (en)	1979-10-09	Novel monoesters of cis-cyclopentenediol, process for preparation thereof, and process for preparation of lactones from the monoesters
HU189582B (en)	1986-07-28	Process for preparing 7-/4-substituted cyclopent-2-en-1-on-2-yl/-hept-2-trans-enoates, 2-arylthio-alkane-dicarboxylic acids and furyl derivatives thereof
US4547586A (en)	1985-10-15	Preparation of 2-isopropenyl-or 2-isopropylidenyl-3-hexenoates from chrysanthemic acid esters
US3901923A (en)	1975-08-26	Acylated bicyclic lactones
Cao et al.	1997	A simple approach to the synthesis of ethyl 2-ethoxy-4-methoxy-6-perfluoroalkylbenzoates via acyclic precursors
SU1291587A1 (ru)	1987-02-23	Способ получени простагландина @ 2 @ или его аналогов
Shi et al.	2000	Synthesis and biological activity of O, O′‐dialkyl‐5‐aryl‐1‐hydroxy‐2E, 4E‐pentadienylphosphonates
Ding et al.	1995	Synthesis of dimethyl 3‐perfluoroalkyl‐4‐(3‐oxo‐2‐triphenyl‐phosphoranylidenbutanylidene)‐pent‐2‐enedioate and its cyclization
US4299972A (en)	1981-11-10	Preparation of cyclopropanecarboxylic acid esters
US4808340A (en)	1989-02-28	Process for preparing methyl 4-oxo-5-tetradecynoate
US4217284A (en)	1980-08-12	Process for preparation of optically pure lactones from monoesters of cis-cyclopentenediol
US3930023A (en)	1975-12-30	Insect control with certain synthetic hormones
US4309563A (en)	1982-01-05	Xylylene diol derivative