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    PRODUCTION OF OPTICALLY ACTIVE 4-HYDROXYCYCLOPENTENONE
    51.
    发明专利
    PRODUCTION OF OPTICALLY ACTIVE 4-HYDROXYCYCLOPENTENONE 失效

    公开(公告)号：JPS62223149A

    公开(公告)日：1987-10-01

    申请号：JP6693286

    申请日：1986-03-25

    申请人： SUMITOMO CHEMICAL CO

    发明人： MINAMII MASAYOSHI

    IPC分类号： C12P41/00 ,  B01J21/00 ,  B01J21/04 ,  C07B31/00 ,  C07B53/00 ,  C07B61/00 ,  C07C45/00 ,  C07C45/51 ,  C07C45/67 ,  C07C49/707 ,  C07C49/743 ,  C07C67/00 ,  C12P7/26

    摘要： PURPOSE:To obtain the titled compound which is an intermediate for agricultural chemicals, medicines, etc., in high purity, by rearranging a 4-cyclopentenone ester having particularly improved substrate specificity for enzymes and cis configuration as a raw material compound while retaining the steric configuration. CONSTITUTION:An optically active 4-cyclopentanone alcohol expressed by formula I (R is alkyl, alkenyl or alkynyl, provided that the substituent group R at the 2-position and the hydroxyl group at the 3-position are cis configuration) as a raw material is rearranged in the presence of a base or catalyst while retaining the steric configuration to afford the aimed compound expressed by formula II. For example, triethylamine, alumina, caustic soda, etc., may be used as the base or catalyst. The compound expressed by formula I is synthesized by asymmetrically hydrolyzing a compound expressed by formula III (R1 is acyloxyl, provided that the substituent group R at the 2-position and the substituent group R1 at the 3-position are cis configuration) using an enzyme or microorganism.

    Preparation of 2,3-disubstituted-4-substituted cyclopentanone
    58.
    发明专利
    Preparation of 2,3-disubstituted-4-substituted cyclopentanone 失效
    2,3-取代的4-取代的环戊烷酮的制备

    公开(公告)号：JPS61115044A

    公开(公告)日：1986-06-02

    申请号：JP23530784

    申请日：1984-11-09

    申请人： Teijin Ltd

    发明人： NOYORI RYOJI ,  SUZUKI MASAAKI ,  TANAKA TOSHIO ,  KUROZUMI SEIJI

    IPC分类号： C07C49/753 ,  B01J31/12 ,  C07B61/00 ,  C07C45/69 ,  C07C49/493 ,  C07C49/517 ,  C07C49/743 ,  C07F7/18

    CPC分类号： Y02P20/52

    摘要： PURPOSE: To obtain efficiently the titled compound through a short process, by subjecting 4-substituted-2-cyclopentenones to conjugate addition reaction with an organo copper compound, followed by directly alkylating the resultant enolated intermediate with a Β, γ-unsaturated conpound in the presence of alkyltins.
    CONSTITUTION: 4-Substituted-2-cyclopentenones expressed by formula I(R
    2 represents trihydrocarbonsilyl group or group forming an acetal bonding together with O atom OH), its enantiomer or mixture thereof in any ratio is subjected to conjugate addition reactuion with an organocopper compound obtained from both an organolithium com pound expressed by formula II (RB is alkyl, etc.) and a copper compound expressed by formula II (Q represents halogen atom, cyano, etc.) preferably in the presence of an organic phosphorus, followed by being reacted with a Β, γ-unsaturated compound expressed by formula V (RA is alkyl; X is halogen, etc.; Z is ethynylene, etc.) in the presence of alkyltins expressed by formula IV (R represents cycloalkyl, etc.; Y represents halogen atom, etc.) to obtain the compound expressed by formula VI, its enantiomer or mixture thereof in any ratio.
    USE: A raw material for PGEs and PGFs.
    COPYRIGHT: (C)1986,JPO&Japio

    摘要翻译： 目的：为了通过短时间的方法有效地获得标题化合物，通过使4-取代-2-环戊烯酮与有机铜化合物进行加成反应，然后直接用BETA，γ-不饱和键结合烷基化，在 烷基化合物的存在。 构成：将由式I表示的4-取代的2-环戊烯酮（R 2表示与O原子OH一起形成缩醛键的三烃基甲硅烷基或基团），其任何比例的对映异构体或其混合物进行共轭加成反应， 由式II表示的有机锂化合物（RB是烷基等）和由式II表示的铜化合物（Q表示卤素原子，氰基等）优选在有机磷存在下获得的有机铜化合物，随后 在由式Ⅳ表示的烷基the the the IV IV etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc.（RA X X X X X X .; .; .; etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. etc. ; Y表示卤素原子等），以任何比例得到由式VI表示的化合物，其对映异构体或其混合物。 用途：PGEs和PGF的原料。