JPS61118345A - シクロヘキセン誘導体 - Google Patents

シクロヘキセン誘導体

Info

Publication number: JPS61118345A
Authority: JP; Japan
Prior art keywords: compound; formula; group; reaction; lower alkyl
Prior art date: 1984-11-14
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.): Granted

Application number

JP23989584A

Other languages

English (en)

Japanese (ja)

Other versions

JPH051774B2 (de

Inventor

Yasumitsu Tamura

田村　恭光

Manabu Sasho

学佐生

Hiroko Oe

大江　寛子

Shuji Akai

周司赤井

Yasuyuki Kita

泰行北

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.)

Individual

Original Assignee

Individual

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.)

1984-11-14

Filing date

1984-11-14

Publication date

1986-06-05

1984-11-14 Application filed by Individual filed Critical Individual

1984-11-14 Priority to JP23989584A priority Critical patent/JPS61118345A/ja

1986-06-05 Publication of JPS61118345A publication Critical patent/JPS61118345A/ja

1993-01-11 Publication of JPH051774B2 publication Critical patent/JPH051774B2/ja

Status Granted legal-status Critical Current

Links

125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 title claims 2
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 4
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
150000001875 compounds Chemical class 0.000 abstract description 43
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 4
238000007363 ring formation reaction Methods 0.000 abstract description 3
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 abstract 1
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 abstract 1
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
-1 alkyl lithium Chemical compound 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
150000007514 bases Chemical class 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
229910052744 lithium Inorganic materials 0.000 description 4
238000000034 method Methods 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
229930195734 saturated hydrocarbon Natural products 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
241000283690 Bos taurus Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000010446 mirabilite Substances 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 3
239000002904 solvent Substances 0.000 description 3
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
235000015278 beef Nutrition 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000005828 desilylation reaction Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
229910000103 lithium hydride Inorganic materials 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229910052775 Thulium Inorganic materials 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000012267 brine Substances 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
235000015111 chews Nutrition 0.000 description 1
UETQVDZZPKAQIC-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl.Cl UETQVDZZPKAQIC-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical group CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 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
239000011541 reaction mixture Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000010902 straw Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1

Landscapes

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

JP23989584A 1984-11-14 1984-11-14 シクロヘキセン誘導体 Granted JPS61118345A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP23989584A JPS61118345A (ja)	1984-11-14	1984-11-14	シクロヘキセン誘導体

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP23989584A JPS61118345A (ja)	1984-11-14	1984-11-14	シクロヘキセン誘導体

Publications (2)

Publication Number	Publication Date
JPS61118345A true JPS61118345A (ja)	1986-06-05
JPH051774B2 JPH051774B2 (de)	1993-01-11

Family

ID=17051453

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP23989584A Granted JPS61118345A (ja)	1984-11-14	1984-11-14	シクロヘキセン誘導体

Country Status (1)

Country	Link
JP (1)	JPS61118345A (de)

1984
- 1984-11-14 JP JP23989584A patent/JPS61118345A/ja active Granted

Also Published As

Publication number	Publication date
JPH051774B2 (de)	1993-01-11

Publication	Publication Date	Title
Harding et al.	1981	Synthesis of trans-2, 5-dimethylpyrrolidine by intramolecular amidomercuration
SU991947A3 (ru)	1983-01-23	Способ получени @ -пиронов
JPS61118345A (ja)	1986-06-05	シクロヘキセン誘導体
Brown et al.	1986	Vinylic organoboranes. 4. A general, one-pot synthesis of 6-and 7-alkyn-1-ols via boracyclanes. Influence of steric effects in the iodination of lithium alkynyl ate complexes of dialkylborinates
JPH0341049A (ja)	1991-02-21	置換３―ホルミル―３―ブテン―１―酸の製造法
DE19853558A1 (de)	2000-05-31	Verfahren zur Herstellung von 2,3-Dihydroindolen (Indolinen), neuartige 2,3-Dihydroindole sowie deren Verwendung
JPH0220638B2 (de)	1990-05-10
Bhat et al.	1971	Synthesis of indole-2-carbaldehydes, 2-(2-aminoethyl)-and 2-(2-aminopropyl)-indoles
Sum et al.	1977	Alkylation of β-keto-ester dianions with α-chloroethers
JP3495774B2 (ja)	2004-02-09	１−ヒドロキシインドール類の製法
Attanasi et al.	1986	Synthesis of new 1-alkoxycarbonylamino-3-sulfonylpyrroles by reaction of (alkoxycarbonylazo) alkenes with. BETA.-keto sulfones.
Ungefug et al.	1973	West synthesis of hexabromocyclopentadiene
DK151630B (da)	1987-12-21	Analogifremgangsmaade til fremstilling af n-phthalidyl-5-fluoruracilderivater
JPS63211264A (ja)	1988-09-02	インドリン類の製造法
CA2413037C (en)	2007-06-26	Intermediates for producing antitumor indolopyrrolocarbazole derivatives
JPS61289077A (ja)	1986-12-19	２，３，５−トリ置換ピリジン誘導体の製法
JPH0278643A (ja)	1990-03-19	新規なトリフルオロアセト酢酸エステルおよびトリフルオロメチルケトンならびにそれらの製造法
JPH0499740A (ja)	1992-03-31	２―ヒドロキシ―２，５，５，９―テトラメチルデカリルエタノールの製造法
JPH0597735A (ja)	1993-04-20	光学活性二級アルコ−ルの製造方法
JPH02290886A (ja)	1990-11-30	（シス‐２‐ブテニル）ジメチルクロロシランの製造法
JPS6130660B2 (de)	1986-07-15
JPS5951534B2 (ja)	1984-12-14	２−アミノ−３−ヒドロキシピリジン誘導体の製造法
Denny Jr et al.	1968	Phenyl ester of lactic acid
JPS6219598A (ja)	1987-01-28	２，３，２′，３′−テトラ−Ｏ−アルキル−α，α−トレハロ−ス誘導体
JPS59181251A (ja)	1984-10-15	ベンゾフエノン−２−カルバメ−ト誘導体