WO2009028284A1 - （Ｒ）－２－アルキルシクロペンタノンおよび（Ｒ）－δ－ラクトンの製造方法 - Google Patents

（Ｒ）－２－アルキルシクロペンタノンおよび（Ｒ）－δ－ラクトンの製造方法 Download PDF

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Publication number
WO2009028284A1
WO2009028284A1 PCT/JP2008/063365 JP2008063365W WO2009028284A1 WO 2009028284 A1 WO2009028284 A1 WO 2009028284A1 JP 2008063365 W JP2008063365 W JP 2008063365W WO 2009028284 A1 WO2009028284 A1 WO 2009028284A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkylcyclopentanone
lactone
produce
production
alkyllactone
Prior art date
Application number
PCT/JP2008/063365
Other languages
English (en)
French (fr)
Inventor
Toru Tachihara
Akira Nakanishi
Shigeyuki Tamogami
Original Assignee
T.Hasegawa Co., Ltd.
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.)
Filing date
Publication date
Priority claimed from JP2007222577A external-priority patent/JP4789889B2/ja
Priority claimed from JP2007230305A external-priority patent/JP5030100B2/ja
Application filed by T.Hasegawa Co., Ltd. filed Critical T.Hasegawa Co., Ltd.
Publication of WO2009028284A1 publication Critical patent/WO2009028284A1/ja

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • C12P7/26—Ketones
    • C12P7/38—Cyclopentanone- or cyclopentadione-containing products

Abstract

【課題】簡便、かつ安価な方法で、環境的に負荷をかけることなく、高収率、高光学純度で、香料等として有用な（Ｒ）－２－アルキルシクロペンタノンおよび（Ｒ）－δ－ラクトンの製造方法を提供する。 【解決手段】２－アルキルシクロペンテノールエステルを、カンディダ・アンタークティカ（Ｃａｎｄｉｄａ　ａｎｔａｒｃｔｉｃａ）由来のリパーゼを用いて不斉加水分解することにより、（Ｒ）－２－アルキルシクロペンタノンを製造し、得られた（Ｒ）－２－アルキルシクロペンタノンを、弱塩基性塩の存在下で、過酢酸を用いて酸化することにより、（Ｒ）－δ－アルキルラクトンを製造する。
PCT/JP2008/063365 2007-08-29 2008-07-25 （Ｒ）－２－アルキルシクロペンタノンおよび（Ｒ）－δ－ラクトンの製造方法 WO2009028284A1 (ja)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2007222577A JP4789889B2 (ja) 2007-08-29 2007-08-29 （ｒ）−２−アルキルシクロペンタノンの製造方法
JP2007-222577 2007-08-29
JP2007-230305 2007-09-05
JP2007230305A JP5030100B2 (ja) 2007-09-05 2007-09-05 光学活性δ−ラクトンの製造方法

Publications (1)

Publication Number Publication Date
WO2009028284A1 true WO2009028284A1 (ja) 2009-03-05

Family

ID=40387012

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/063365 WO2009028284A1 (ja) 2007-08-29 2008-07-25 （Ｒ）－２－アルキルシクロペンタノンおよび（Ｒ）－δ－ラクトンの製造方法

Country Status (1)

Country Link
WO (1) WO2009028284A1 (ja)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014024886A1 (ja) * 2012-08-06 2014-02-13 日産化学工業株式会社 エピ体含有量の多いジャスモン酸メチル異性体組成物の製造方法
CN113861146A (zh) * 2021-10-29 2021-12-31 安徽华业香料合肥有限公司 一种天然δ-癸内酯的合成工艺

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63293A (ja) * 1986-06-18 1988-01-05 Sumitomo Chem Co Ltd 光学活性な４−ヒドロキシ−２−シクロペンテノンの製造方法
JPS6366143A (ja) * 1986-09-08 1988-03-24 Sumitomo Chem Co Ltd 光学活性シクロペンテノンアルコ−ル類の製造方法
JP2004352636A (ja) * 2003-05-28 2004-12-16 Takasago Internatl Corp ラクトン類又はエステル類の製造方法

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63293A (ja) * 1986-06-18 1988-01-05 Sumitomo Chem Co Ltd 光学活性な４−ヒドロキシ−２−シクロペンテノンの製造方法
JPS6366143A (ja) * 1986-09-08 1988-03-24 Sumitomo Chem Co Ltd 光学活性シクロペンテノンアルコ−ル類の製造方法
JP2004352636A (ja) * 2003-05-28 2004-12-16 Takasago Internatl Corp ラクトン類又はエステル類の製造方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014024886A1 (ja) * 2012-08-06 2014-02-13 日産化学工業株式会社 エピ体含有量の多いジャスモン酸メチル異性体組成物の製造方法
CN113861146A (zh) * 2021-10-29 2021-12-31 安徽华业香料合肥有限公司 一种天然δ-癸内酯的合成工艺

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