hydroxy-[5-(2-methyl-4-nitrophenyl)-furan-2-yl]acetonitrile | 601464-32-8

• 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: hydroxy-[5-(2-methyl-4-nitrophenyl)-furan-2-yl]acetonitrile
• CAS: 601464-32-8
• 化学式: C₁₃H₁₀N₂O₄
• 分子量: 258.233
• InChiKey: IUUUWULHWXLZCI-UHFFFAOYSA-N

物化性质

• 沸点：
  435.5±45.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  100.3
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  hydroxy-[5-(2-methyl-4-nitrophenyl)-furan-2-yl]acetonitrile 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 Pseudomonas cepacia lipase 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 50.0h， 生成 (S)-[5-(2-methyl-4-nitrophenyl)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
• 作为产物：
  描述：

  5-nitro-toluene-2-diazonium ; chloride 在 盐酸 、 copper(l) chloride 、 zinc(II) iodide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 hydroxy-[5-(2-methyl-4-nitrophenyl)-furan-2-yl]acetonitrile
  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.