(R,S)-cyano(3-phenoxyphenyl)methyl butyrate | 120838-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,S)-cyano(3-phenoxyphenyl)methyl butyrate
• 英文别名: (RS)-cyano(3-phenoxyphenyl)methyl butyrate；[Cyano-(3-phenoxyphenyl)methyl] butanoate
• CAS: 120838-94-0
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: JZTLZAUEQAEOAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,S)-cyano(3-phenoxyphenyl)methyl butyrate 在 Pseudomonas cepacia lipase immobilised in a gelatin matrix 、 正丁醇 作用下， 以 正己烷 为溶剂， 反应 8.0h， 以85%的产率得到(S)-(3-苯氧基苯基)羟基乙腈
  参考文献：
  名称：

  ‘Gelozymes’ in organic synthesis: synthesis of enantiomerically pure (S)-2-hydroxy-(3-phenoxy)phenylacetonitrile with lipase immobilised in a gelatin matrix

  摘要：

  Lipase from Pseudomonas cepacia (Amano PS and PS Lipase, Fluka) immobilised in microemulsion-based organogels formed by gelatin solubilisation and crosslinking with glutaraldehyde ('Gelozyme') has been used for the alcoholysis of the butanoate ester of racemic 2-hydroxy-(3-phenoxy)phenylacetonitrile with 1-butanol in hexane to obtain (S)-2-hydroxy-(3-phenoxy)phenylacetonitrile. The immobilised enzyme can be used over 25 days (25 cycles) without significant loss of enzyme activity (<10%). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00303-7
• 作为产物：
  描述：

  三苯氧基苯甲醛 、 丁酰氯 在 吡啶 、 丙醇 、 4-二甲氨基吡啶 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以84%的产率得到(R,S)-cyano(3-phenoxyphenyl)methyl butyrate
  参考文献：
  名称：

  受保护的氰醇的对映选择性合成

  摘要：

  已经建立了制备光学活性受保护的氰醇的简单方法，该氰醇是合成药物和农用化学品的重要组成部分。来自南极念珠菌 (CAL-B) 的脂肪酶 B 在温和条件下催化外消旋醋酸氰的动力学拆分。所得不稳定的氰醇通过酶催化途径（包括加入丁酸乙烯酯）或在从反应混合物中除去酶后以化学方式再保护。该过程使两种对映异构体均以纯形式和良好的产率获得，同时显着降低了 HCN 引起的风险。还引入了各种不同的保护基团。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200205)2002:9<1516::aid-ejoc1516>3.0.co;2-c

文献信息

• Novel porous vessel bioreactor
  申请人：——

  公开号：US20040110280A1

  公开（公告）日：2004-06-10

  The present invention provides a porous vessel bioreactor apparatus for use in reaction with immobilized enzymes and/or microbial cells, said apparatus consisting of a vertically elongated reaction vessel having at least one liquid reactant inlet; at least one product outlet on the vessel; at least one porous vessel completely submerged in the reactant, said porous vessel having pore size ranging from 5 mm to 0.2 microns and a vertical length less than a level of the reactants to be maintained in the vessel, and immobilized bio-catalyst particles comprising the enzymes and/or microbial cells placed inside the porous vessel such that the liquid reactant is in contact with the bio-catalyst in both radial and axial directions.

  本发明提供了一种多孔容器生物反应器装置，用于与固定酶和/或微生物细胞反应，该装置由至少具有一个液体反应物进口的垂直延长反应容器、至少一个容器上的产物出口、至少一个完全浸没在反应物中的多孔容器组成，该多孔容器具有孔径范围从5毫米到0.2微米，垂直长度小于要保持在容器中的反应物的水平面，并且将固定的生物催化剂颗粒（包括酶和/或微生物细胞）放置在多孔容器内，以使液体反应物在径向和轴向方向上与生物催化剂接触。
• Method for biotechnologically preparing (S)-(-)-alpha-cyano-3-phenoxybenzyl alcohol
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0080827A2

  公开（公告）日：1983-06-08

  (S)-(-)-α-cyano-3-phenoxybenzyl alcohol, which is the alcohol moiety of pyrethroids, effective insecticides, is prepared by reacting organic carboxylic acid ester, such as acetic acid ester, of racemic (R.S)-α-cyano-3-phenoxybenzyl alcohol with an esterase, wherein the ester of (S)-(-)-α-cyano-3-phenoxybenzyl alcohol is predominantly hydrolyzed. Thus. asymmetric hydrolysis permits optical resolution of the (S)-(-)-isomer alcohol from the ester of its antipode, in a high optical purity. The esterase may be of microorganism or animal pancreas or liver.

  (S)-(-)-α-氰基-3-苯氧基苄醇是有效杀虫剂拟除虫菊酯的醇基，其制备方法是将外消旋(R.S)-α-氰基-3-苯氧基苄醇的有机羧酸酯（如乙酸酯）与酯酶反应，其中(S)-(-)-α-氰基-3-苯氧基苄醇的酯主要被水解。 因此，不对称水解允许以高光学纯度从其反式的酯中光学分解出(S)-(-)-异构体醇。 酯酶可以是微生物或动物的胰腺或肝脏。
• ‘Gelozymes’ in organic synthesis. Part 2: Candida rugosa lipase mediated synthesis of enantiomerically pure (S)-cyano(3-phenoxyphenyl)methyl butyrate
  作者：Nitin W. Fadnavis、Ravi Luke Babu、Gurrala Sheelu、Ashlesha Deshpande

  DOI：10.1016/s0957-4166(01)00277-4

  日期：2001.7

  Significant changes in enantioselectivity (E) have been observed when the butanoate ester of ()-1-hydroxy-1-(3-phenoxyphenyl)acetonitrile was subjected to hydrolysis in acetate buffer (pH 4.5 E=6.4) and alcoholysis with 1-butanol in hexane catalysed by Candida rugosa lipase (E=45). Enantiomerically pure (S)-butanoate ester so obtained (e.e. 98.4%) was converted to the corresponding (S)-cyanohydrin using Pseudomonas cepacia (Amano Ps) gelozyme. This strategy overcomes the problem of separation of the unwanted (R)-ester from the (S)-cyanohydrin. (C) 2001 Elsevier Science Ltd. All rights reserved.
• ROPER, JERRY M.
  作者：ROPER, JERRY M.

  DOI：——

  日期：——
• POROUS VESSEL BIOREACTOR
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：EP1570044B1

  公开（公告）日：2007-03-21