(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate | 67614-32-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
• 英文别名: (S)-α-Cyano-3-phenoxybenzyl (R)-2-(4-chlorophenyl)isovalerate；(2R, αS)-fenvalerate；(2R,αS)-fenvalerate；(1R,2S)-fenvalerate；(S,R)-fenvalerate；fenvalerate；[cyano-(3-phenoxyphenyl)methyl] (2R)-2-(4-chlorophenyl)-3-methylbutanoate
• CAS: 67614-32-8
• 化学式: C₂₅H₂₂ClNO₃
• 分子量: 419.908
• InChiKey: NYPJDWWKZLNGGM-XMMISQBUSA-N

物化性质

• 沸点：
  538.9±50.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate 生成 来福灵
  参考文献：
  名称：

  XAYASI, MASAXIRO;SUDZUKI, YUKIO;TAGUMA, KEHNDZI

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-氯苯基)-3-甲基丁酸 在 吡啶 、 氯化亚砜 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 1.5h， 生成 (R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
  参考文献：
  名称：

  Development of an Immunoassay for the Pyrethroid Insecticide Esfenvalerate

  摘要：

  A competitive enzyme-linked immunosorbent assay was developed for the detection of the pyrethroid insecticide esfenvalerate. Two haptens containing amine or propanoic acid groups on the terminal aromatic ring of the fenvalerate molecule were synthesized and coupled to carrier proteins as immunogens. Five antisera were produced and screened against eight different coating antigens. The assay that had the least interference and was the most sensitive for esfenvalerate was optimized and characterized. The I-50 for esfenvalerate was 30 +/- 6.2 mu g/L, and the lower detection limit (LDL) was 3.0 +/- 1.8 mu g/L. The assay was very selective. Other pyrethroid analogues and esfenvalerate metabolites tested did not cross-react significantly in this assay. To increase the sensitivity of the overall method, a C-18 sorbent-based. solid-phase extraction (SPE) was used for water matrix. With this SPE step, the LDL of the overall method for esfenvalerate was 0.1 mu g/L in water samples.

  DOI：

  10.1021/jf981210m

文献信息

• Process for preparing (S)- alpha-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl)-isovalerate
  申请人：Reddy Venkata Narayana Vaddu

  公开号：US20060128982A1

  公开（公告）日：2006-06-15

  The present invention relates to an environmentally benign process for the preparation of (S)-α-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl)isovalerate from its diastereomeric mixture (RS)-α-cyano-3-phenoxybenzyl-(S)-2-(4-chlorophenyl) isovalerate.

  本发明涉及一种环保的工艺，用于从其对映体混合物(RS)-α-氰基-3-苯氧基苯甲酰-(S)-2-(4-氯苯基)异戊酸酯中制备(S)-α-氰基-3-苯氧基苯甲酰-(S)-2-(4-氯苯基)异戊酸酯。
• ‘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.