JPH0566937B2 - - Google Patents

Info

Publication number: JPH0566937B2
Authority: JP; Japan
Prior art keywords: dimethylcyclopropanecarboxylate; ethyl; nmr; formula; propenyl
Prior art date: 1985-04-25
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

JP60087444A

Other languages

English (en)

Japanese (ja)

Other versions

JPS61246149A (ja

Inventor

Tamejiro Hyama

Makoto Fujita

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sagami Chemical Research Institute

Original Assignee

Sagami Chemical Research Institute

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.)

1985-04-25

Filing date

1985-04-25

Publication date

1993-09-22

1985-04-25 Application filed by Sagami Chemical Research Institute filed Critical Sagami Chemical Research Institute

1985-04-25 Priority to JP60087444A priority Critical patent/JPS61246149A/ja

1986-11-01 Publication of JPS61246149A publication Critical patent/JPS61246149A/ja

1993-09-22 Publication of JPH0566937B2 publication Critical patent/JPH0566937B2/ja

Status Granted legal-status Critical Current

Links

125000000217 alkyl group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
238000005481 NMR spectroscopy Methods 0.000 description 15
239000000203 mixture Substances 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
239000000243 solution Substances 0.000 description 14
-1 diazoacetic acid ester Chemical class 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
239000002994 raw material Substances 0.000 description 9
239000002253 acid Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
150000001942 cyclopropanes Chemical class 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
241000723353 Chrysanthemum Species 0.000 description 4
235000007516 Chrysanthemum Nutrition 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
ZFZXRNVTYVRULM-UHFFFAOYSA-N ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=O)C1(C)C ZFZXRNVTYVRULM-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
239000003586 protic polar solvent Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 2
150000001336 alkenes Chemical group 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 2
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Substances CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 2
239000004210 ether based solvent Substances 0.000 description 2
OMQDMPAJKBUQSL-UHFFFAOYSA-N ethyl 2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1(C)C OMQDMPAJKBUQSL-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
ARVALZZVFLDZSO-UHFFFAOYSA-N triethyl(1,2,2-trifluoroethenyl)silane Chemical group CC[Si](CC)(CC)C(F)=C(F)F ARVALZZVFLDZSO-UHFFFAOYSA-N 0.000 description 2
JPRWLTIIUDZUTF-UHFFFAOYSA-N trifluorovinyllithium Chemical compound [Li]C(F)=C(F)F JPRWLTIIUDZUTF-UHFFFAOYSA-N 0.000 description 2
HXNGZCTYVCOMIK-UHFFFAOYSA-N (1-chloro-2,2-difluoroethenyl)-triethylsilane Chemical group CC[Si](CC)(CC)C(Cl)=C(F)F HXNGZCTYVCOMIK-UHFFFAOYSA-N 0.000 description 1
KVTSTCHYBUYVBA-XVNBXDOJSA-N (e)-2-cyano-3-(2,4-dichlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C\C1=CC=C(Cl)C=C1Cl KVTSTCHYBUYVBA-XVNBXDOJSA-N 0.000 description 1
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 1
MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
239000005046 Chlorosilane Substances 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
VQNKMGQVKJNBKQ-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=O)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 VQNKMGQVKJNBKQ-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
CTPBGXQYXMEJIG-UHFFFAOYSA-N benzyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=O)C1C(=O)OCC1=CC=CC=C1 CTPBGXQYXMEJIG-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
238000006704 dehydrohalogenation reaction Methods 0.000 description 1
ZJJSEBQCVBNRST-UHFFFAOYSA-N dimethyl-phenyl-(1,2,2-trifluoroethenyl)silane Chemical group FC(F)=C(F)[Si](C)(C)C1=CC=CC=C1 ZJJSEBQCVBNRST-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
GIGHGCMJPURZJA-UHFFFAOYSA-N ethyl 2,3-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C)C1C GIGHGCMJPURZJA-UHFFFAOYSA-N 0.000 description 1
ZLDOMUPTDYCDBS-UHFFFAOYSA-N ethyl 3,3-dimethylpent-4-enoate Chemical compound CCOC(=O)CC(C)(C)C=C ZLDOMUPTDYCDBS-UHFFFAOYSA-N 0.000 description 1
ANNHJHCLRBLWBB-UHFFFAOYSA-N ethyl 3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=C(Cl)C(F)(F)F)C1(C)C ANNHJHCLRBLWBB-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000010410 layer Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
SMPAPEKFGLKOIC-UHFFFAOYSA-N oxolane;hydrochloride Chemical compound Cl.C1CCOC1 SMPAPEKFGLKOIC-UHFFFAOYSA-N 0.000 description 1
238000005949 ozonolysis reaction Methods 0.000 description 1
XNOYKTJSHCQKHH-UHFFFAOYSA-N phenyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=O)C1C(=O)OC1=CC=CC=C1 XNOYKTJSHCQKHH-UHFFFAOYSA-N 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
HIHYQHFFHYZPMR-UHFFFAOYSA-N tris(diethylamino)sulfanium Chemical compound CCN(CC)[S+](N(CC)CC)N(CC)CC HIHYQHFFHYZPMR-UHFFFAOYSA-N 0.000 description 1
PGOLTJPQCISRTO-UHFFFAOYSA-N vinyllithium Chemical compound [Li]C=C PGOLTJPQCISRTO-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP60087444A 1985-04-25 1985-04-25 シクロプロパン誘導体 Granted JPS61246149A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60087444A JPS61246149A (ja)	1985-04-25	1985-04-25	シクロプロパン誘導体

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60087444A JPS61246149A (ja)	1985-04-25	1985-04-25	シクロプロパン誘導体

Publications (2)

Publication Number	Publication Date
JPS61246149A JPS61246149A (ja)	1986-11-01
JPH0566937B2 true JPH0566937B2 (cs)	1993-09-22

Family

ID=13915029

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60087444A Granted JPS61246149A (ja)	1985-04-25	1985-04-25	シクロプロパン誘導体

Country Status (1)

Country	Link
JP (1)	JPS61246149A (cs)

1985
- 1985-04-25 JP JP60087444A patent/JPS61246149A/ja active Granted

Also Published As

Publication number	Publication date
JPS61246149A (ja)	1986-11-01

Publication	Publication Date	Title
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