hydroxy-[5-(4-bromophenyl)-furan-2-yl]acetonitrile | 601464-30-6

• 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-(4-bromophenyl)-furan-2-yl]acetonitrile
• 英文别名: 2-[5-(4-bromophenyl)furan-2-yl]-2-hydroxyacetonitrile
• CAS: 601464-30-6
• 化学式: C₁₂H₈BrNO₂
• 分子量: 278.105
• InChiKey: HEAKKZZNIYELEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  409.8±45.0 °C(Predicted)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  hydroxy-[5-(4-bromophenyl)-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 (R)-hydroxy-[5-(4-bromophenyl)-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
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 生成 hydroxy-[5-(4-bromophenyl)-furan-2-yl]acetonitrile
  参考文献：
  名称：

  Substituent effects on the stereochemical outcome of the baker’s yeast-mediated biotransformation of α-hydroxy- and α-acetoxymethyl-5-phenylfuran-2-yl-ethanones

  摘要：

  In this Letter the baker's yeast-mediated biotransformation of variously substituted alpha-hydroxy- and alpha-acetoxymethyl-5-phenylfuran-2-yl-ethanones is described. The stereochemical outcome of the reactions was strongly influenced by the nature of the substituents on the phenyl ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.004