2-methoxy-N-[(1R)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]acetamide | 1260955-15-4

• 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-methoxy-N-[(1R)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]acetamide
• CAS: 1260955-15-4
• 化学式: C₁₇H₂₆BNO₄
• 分子量: 319.209
• InChiKey: MHGTUVHEMMGFQL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲氧基乙酸乙酯 、 4-(1-氨基乙基)苯硼酸频哪醇酯 在 lipase from Candida antarctica 作用下， 以 正己烷 为溶剂， 反应 24.0h， 生成 (S)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanamine 、 (R)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanamine 、 2-methoxy-N-[(1R)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]acetamide
  参考文献：
  名称：

  Chemoenzymatic synthesis of boron-containing chiral amines and amides

  摘要：

  The first application of lipases as catalysts to obtain optically active boron-containing amines and amides is described. We studied several reaction conditions to achieve the kinetic resolution of boron-containing amines via enantioselective acylation mediated by Candida antarctica lipase B (CAL-B). Excellent enantioselectivity (E>200) and high enantiomeric excess (up to >99%) of both the remaining amines and amides were obtained. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.09.011

文献信息

• Chemoenzymatic synthesis of boron-containing chiral amines and amides
  作者：Leandro H. Andrade、Thiago Barcellos、Carolina G. Santiago

  DOI：10.1016/j.tetasy.2010.09.011

  日期：2010.10

  The first application of lipases as catalysts to obtain optically active boron-containing amines and amides is described. We studied several reaction conditions to achieve the kinetic resolution of boron-containing amines via enantioselective acylation mediated by Candida antarctica lipase B (CAL-B). Excellent enantioselectivity (E>200) and high enantiomeric excess (up to >99%) of both the remaining amines and amides were obtained. (C) 2010 Elsevier Ltd. All rights reserved.