(S)-[5-(2-chlorophenyl)furan-2-yl]cyanomethyl butanoate

• 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: (S)-[5-(2-chlorophenyl)furan-2-yl]cyanomethyl butanoate
• 英文别名: [(S)-[5-(2-chlorophenyl)furan-2-yl]-cyanomethyl] butanoate
• 化学式: C₁₆H₁₄ClNO₃
• 分子量: 303.745
• InChiKey: YYTWOQFMKRBOPH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-chlorobenzenediazonium chloride 在 盐酸 、 甲醇 、 Pseudomonas cepacia lipase 、 Candida antarctica Lipase A 、 copper(l) chloride 、 zinc(II) iodide 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 99.0h， 生成 (S)-[5-(2-chlorophenyl)furan-2-yl]cyanomethyl butanoate
  参考文献：
  名称：

  Preparation of novel phenylfuran-based cyanohydrin esters: lipase-catalysed kinetic and dynamic resolution

  摘要：

  A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantio selective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yi cyanomethyl butanoates in toluene with E much greater than100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00286-6

文献信息

• Preparation of novel phenylfuran-based cyanohydrin esters: lipase-catalysed kinetic and dynamic resolution
  作者：Csaba Paizs、Petri Tähtinen、Katri Lundell、László Poppe、Florin-Dan Irimie、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(03)00286-6

  日期：2003.7

  A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantio selective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yi cyanomethyl butanoates in toluene with E much greater than100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.