2-phenylacetamido-3,3-dimethylpropionitrile

• 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: 2-phenylacetamido-3,3-dimethylpropionitrile
• 英文别名: N-(1-cyano-2-methylpropyl)-2-phenylacetamide
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: AIIBEZOOCNAIQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基-3-甲基丁腈 、 苯乙酰氯 在 吡啶 作用下， 以 水 为溶剂， 反应 3.0h， 以73%的产率得到2-phenylacetamido-3,3-dimethylpropionitrile
  参考文献：
  名称：

  Enantioselective acylation of α-aminonitriles catalysed by Candida antarctica lipase. An unexpected turnover-related racemisation

  摘要：

  Candida antarctica lipase B (Novozyme 435) catalysed the enantioselective acylation of 2-amino-2-phenylacetonitrile 1 with ethyl phenylacetate affording a near enantiopure product in 47% yield. Acylation of 1 and 2-amino-4-phenylbutyronitrile with ethyl acetate yielded an unexpected partially racemised final product. The racemisation was shown to be turnover related and is ascribed to the increased acidity of the alpha -proton in the formation of the tetrahedral intermediate in the active site of the enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00011-8

文献信息

• Enantioselective acylation of α-aminonitriles catalysed by Candida antarctica lipase. An unexpected turnover-related racemisation
  作者：P. López-Serrano、J.A. Jongejan、F. van Rantwijk、R.A. Sheldon

  DOI：10.1016/s0957-4166(01)00011-8

  日期：2001.2

  Candida antarctica lipase B (Novozyme 435) catalysed the enantioselective acylation of 2-amino-2-phenylacetonitrile 1 with ethyl phenylacetate affording a near enantiopure product in 47% yield. Acylation of 1 and 2-amino-4-phenylbutyronitrile with ethyl acetate yielded an unexpected partially racemised final product. The racemisation was shown to be turnover related and is ascribed to the increased acidity of the alpha -proton in the formation of the tetrahedral intermediate in the active site of the enzyme. (C) 2001 Elsevier Science Ltd. All rights reserved.