N-[(S)-(-)-1-phenylethyl]decanamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-[(S)-(-)-1-phenylethyl]decanamide
• 英文别名: N-[(1S)-1-phenylethyl]decanamide
• 化学式: C₁₈H₂₉NO
• 分子量: 275.434
• InChiKey: JLSGGIBTZLSVMF-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  正癸酸 、 (S)-(-)- α-甲基苄胺 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到N-[(S)-(-)-1-phenylethyl]decanamide
  参考文献：
  名称：

  ‘Easy-on, easy-off’ resolution of chiral 1-phenylethylamine catalyzed by Candida antarctica lipase B

  摘要：

  An 'easy-on, easy-oft process for the effective resolution of (+/-)-1-phenylethylamine was designed using the lipase B of Candida antarctica. This two step lipase-catalyzed process for the resolution of a chiral arylalkylamine involves a high-conversion enantioselective condensation of (R)-(+)-1-phenylethylamine with capric acid (conversion 99%, <24 h), followed by the hydrolysis of the corresponding synthesized (R)-(+)-amide (conversion 98%, 48 h). As a result, this efficient enzymatic process yields both (R)- and (S)-enantiomers of I-phenylethylamine in high enantiomeric purity. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.045

文献信息

• ‘Easy-on, easy-off’ resolution of chiral 1-phenylethylamine catalyzed by Candida antarctica lipase B
  作者：A. Torres-Gavilán、J. Escalante、I. Regla、A. López-Munguía、E. Castillo

  DOI：10.1016/j.tetasy.2007.10.045

  日期：2007.11

  An 'easy-on, easy-oft process for the effective resolution of (+/-)-1-phenylethylamine was designed using the lipase B of Candida antarctica. This two step lipase-catalyzed process for the resolution of a chiral arylalkylamine involves a high-conversion enantioselective condensation of (R)-(+)-1-phenylethylamine with capric acid (conversion 99%, <24 h), followed by the hydrolysis of the corresponding synthesized (R)-(+)-amide (conversion 98%, 48 h). As a result, this efficient enzymatic process yields both (R)- and (S)-enantiomers of I-phenylethylamine in high enantiomeric purity. (c) 2007 Elsevier Ltd. All rights reserved.