2-oxo-pyrrolidine-1-carboxylic acid 2-(1S,2R)-(1-methyl-1-phenylethyl)cyclohexyl ester | 681006-04-2

• 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-oxo-pyrrolidine-1-carboxylic acid 2-(1S,2R)-(1-methyl-1-phenylethyl)cyclohexyl ester
• CAS: 681006-04-2
• 化学式: C₂₀H₂₇NO₃
• 分子量: 329.439
• InChiKey: SVXQUANRRMYPJK-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-oxo-pyrrolidine-1-carboxylic acid 2-(1S,2R)-(1-methyl-1-phenylethyl)cyclohexyl ester 在 4 A molecular sieve 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 2-(R*,S*)-benzotriazolyl-pyrrolidine-1-carboxylic acid 2-(1S,2R)-(1-methyl-1-phenylethyl)cyclohexyl ester
  参考文献：
  名称：

  Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines

  摘要：

  trans-Cumylcyclohexanol (TCC) is used as a chiral auxiliary for the stereoselective addition of tributyltinlithium to N-acylpyrrolidinium/piperidinium ion with 70-80% diastereoselectivity at 0degreesC. After removal of the minor diastereomer by radial chromatography, enantiopure N-methyl-2-(tributylstannyl)pyrrolidine and piperidine were produced by reductive removal of the auxiliary. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.080
• 作为产物：
  描述：

  (1S,2R)-(+)-反-2-(1-甲基-1-苯乙基)环己醇 在 喹啉 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 23.25h， 生成 2-oxo-pyrrolidine-1-carboxylic acid 2-(1S,2R)-(1-methyl-1-phenylethyl)cyclohexyl ester
  参考文献：
  名称：

  Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines

  摘要：

  trans-Cumylcyclohexanol (TCC) is used as a chiral auxiliary for the stereoselective addition of tributyltinlithium to N-acylpyrrolidinium/piperidinium ion with 70-80% diastereoselectivity at 0degreesC. After removal of the minor diastereomer by radial chromatography, enantiopure N-methyl-2-(tributylstannyl)pyrrolidine and piperidine were produced by reductive removal of the auxiliary. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.080