JPS6054335A - （−）−（ｒ）−２−メチル−４−ヘキセン酸 - Google Patents

（−）−（ｒ）−２−メチル−４−ヘキセン酸

Info

Publication number: JPS6054335A
Authority: JP; Japan
Prior art keywords: methyl; formula; hexenoic acid; useful; compound
Prior art date: 1983-09-01
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

JP15905583A

Other languages

English (en)

Japanese (ja)

Other versions

JPH032129B2 (pl

Inventor

Takeshi Nakai

武中井

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.)

Takasago International Corp

Takasago Corp

Original Assignee

Takasago International Corp

Takasago Perfumery Industry Co

Takasago Corp

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.)

1983-09-01

Filing date

1983-09-01

Publication date

1985-03-28

1983-09-01 Application filed by Takasago International Corp, Takasago Perfumery Industry Co, Takasago Corp filed Critical Takasago International Corp

1983-09-01 Priority to JP15905583A priority Critical patent/JPS6054335A/ja

1985-03-28 Publication of JPS6054335A publication Critical patent/JPS6054335A/ja

1991-01-14 Publication of JPH032129B2 publication Critical patent/JPH032129B2/ja

Status Granted legal-status Critical Current

Links

XTQLWNAWEPKOLB-ZCFIWIBFSA-N (2R)-2-methylhex-3-enoic acid Chemical compound C[C@@H](C(=O)O)C=CCC XTQLWNAWEPKOLB-ZCFIWIBFSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract description 11
LVRUXBYMNQLOGH-LURJTMIESA-N [(2s)-but-3-en-2-yl] propanoate Chemical compound CCC(=O)O[C@@H](C)C=C LVRUXBYMNQLOGH-LURJTMIESA-N 0.000 abstract description 10
230000003287 optical effect Effects 0.000 abstract description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract description 9
239000002904 solvent Substances 0.000 abstract description 6
GKPOMITUDGXOSB-BYPYZUCNSA-N (2s)-but-3-yn-2-ol Chemical compound C[C@H](O)C#C GKPOMITUDGXOSB-BYPYZUCNSA-N 0.000 abstract description 5
230000015572 biosynthetic process Effects 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 4
239000000463 material Substances 0.000 abstract description 3
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 abstract description 3
238000005821 Claisen rearrangement reaction Methods 0.000 abstract description 2
239000011981 lindlar catalyst Substances 0.000 abstract description 2
239000002994 raw material Substances 0.000 abstract description 2
GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 abstract 2
RXJJIFUOUWVKTA-BYPYZUCNSA-N (2s)-2-methyl-4-oxobutanoic acid Chemical compound OC(=O)[C@@H](C)CC=O RXJJIFUOUWVKTA-BYPYZUCNSA-N 0.000 abstract 1
229930003427 Vitamin E Natural products 0.000 abstract 1
229940079593 drug Drugs 0.000 abstract 1
239000003814 drug Substances 0.000 abstract 1
WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 abstract 1
238000002360 preparation method Methods 0.000 abstract 1
230000002194 synthesizing effect Effects 0.000 abstract 1
229940046009 vitamin E Drugs 0.000 abstract 1
235000019165 vitamin E Nutrition 0.000 abstract 1
239000011709 vitamin E Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 8
239000000243 solution Substances 0.000 description 7
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
230000000704 physical effect Effects 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000007704 transition Effects 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229940043279 diisopropylamine Drugs 0.000 description 2
238000000034 method Methods 0.000 description 2
229940088594 vitamin Drugs 0.000 description 2
229930003231 vitamin Natural products 0.000 description 2
235000013343 vitamin Nutrition 0.000 description 2
239000011782 vitamin Substances 0.000 description 2
150000003722 vitamin derivatives Chemical class 0.000 description 2
NIONDZDPPYHYKY-SNAWJCMRSA-N (2E)-hexenoic acid Chemical compound CCC\C=C\C(O)=O NIONDZDPPYHYKY-SNAWJCMRSA-N 0.000 description 1
QDYRHGGXBLRFHS-SNAWJCMRSA-N (e)-4-methylhex-2-enoic acid Chemical compound CCC(C)\C=C\C(O)=O QDYRHGGXBLRFHS-SNAWJCMRSA-N 0.000 description 1
FTHUQCQZQRXJLF-HWKANZROSA-N (e)-5-methylhex-2-enoic acid Chemical compound CC(C)C\C=C\C(O)=O FTHUQCQZQRXJLF-HWKANZROSA-N 0.000 description 1
HFAXNGJLZXRBRG-UHFFFAOYSA-N 2-methylhex-4-enoic acid Chemical compound CC=CCC(C)C(O)=O HFAXNGJLZXRBRG-UHFFFAOYSA-N 0.000 description 1
QDYRHGGXBLRFHS-UHFFFAOYSA-N 4-Methyl-2-hexenoic acid Natural products CCC(C)C=CC(O)=O QDYRHGGXBLRFHS-UHFFFAOYSA-N 0.000 description 1
YJJLHGCCADOOPZ-UHFFFAOYSA-N 5-methylhex-4-enoic acid Chemical compound CC(C)=CCCC(O)=O YJJLHGCCADOOPZ-UHFFFAOYSA-N 0.000 description 1
241001475178 Dira Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000102542 Kara Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000284 extract 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
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
NRUBUZBAZRTHHX-UHFFFAOYSA-N lithium;propan-2-ylazanide Chemical compound [Li+].CC(C)[NH-] NRUBUZBAZRTHHX-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000006462 rearrangement reaction Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
208000026082 sterile multifocal osteomyelitis with periostitis and pustulosis Diseases 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

Landscapes

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

JP15905583A 1983-09-01 1983-09-01 （−）−（ｒ）−２−メチル−４−ヘキセン酸 Granted JPS6054335A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP15905583A JPS6054335A (ja)	1983-09-01	1983-09-01	（−）−（ｒ）−２−メチル−４−ヘキセン酸

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15905583A JPS6054335A (ja)	1983-09-01	1983-09-01	（−）−（ｒ）−２−メチル−４−ヘキセン酸

Publications (2)

Publication Number	Publication Date
JPS6054335A true JPS6054335A (ja)	1985-03-28
JPH032129B2 JPH032129B2 (pl)	1991-01-14

Family

ID=15685233

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15905583A Granted JPS6054335A (ja)	1983-09-01	1983-09-01	（−）−（ｒ）−２−メチル−４−ヘキセン酸

Country Status (1)

Country	Link
JP (1)	JPS6054335A (pl)

1983
- 1983-09-01 JP JP15905583A patent/JPS6054335A/ja active Granted

Also Published As

Publication number	Publication date
JPH032129B2 (pl)	1991-01-14

Publication	Publication Date	Title
JPS63264565A (ja)	1988-11-01	エチニルシクロヘキセン誘導体
JPS6054335A (ja)	1985-03-28	（−）−（ｒ）−２−メチル−４−ヘキセン酸
JP2003321442A (ja)	2003-11-11	新規なジフルオロプロスタグランジンアミド誘導体
JP2546559B2 (ja)	1996-10-23	ジイソピノカンフェイルクロロボランのインシトゥー製造
JPH04134084A (ja)	1992-05-07	ケイ酸エステルおよびその製造方法
JPS63216890A (ja)	1988-09-09	チユアンシンマイシン類縁体の製造方法
JPS61158945A (ja)	1986-07-18	プソイドｉｓｏ−メチルイオノンの製法
JPS59101458A (ja)	1984-06-12	新規なチアプロスタグランジン誘導体及びその製法
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JPS60185791A (ja)	1985-09-21	β−トリアルキルシリル−β，γ−不飽和アルデヒドおよびその製造方法
JPH04128295A (ja)	1992-04-28	１，１，３，３―テトラメチル―１，３―ジシロキサンの製造方法
JPH05202379A (ja)	1993-08-10	持続性香気香味賦与乃至変調剤
JPH04352745A (ja)	1992-12-07	光学活性アルコールの製法
JPS61233646A (ja)	1986-10-17	ポリプレニル−β−ヒドロキシカルボン酸またはそのエステル
JPH01135781A (ja)	1989-05-29	光学活性エポキシ化アルコールおよびその製法
JPS61205243A (ja)	1986-09-11	トレオ−α−置換β−ヒドロキシ酸アミドの製造方法
JPH093055A (ja)	1997-01-07	クロマノン系化合物の製造方法
JPS5869878A (ja)	1983-04-26	ｄｌ−ニコチンの製造法
PL167443B1 (pl)	1995-09-30	Sposób wytwarzania nowych acetali (Z)-3,7-dimetylo-4-okten-1-alu
JPS62111977A (ja)	1987-05-22	２，２ジメチルδバレロラクトンの製造方法