(2S)-methyl 1-(1-(2-chlorophenyl)-2-phenylethyl)pyrrolidine-2-carboxylate | 1262029-33-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S)-methyl 1-(1-(2-chlorophenyl)-2-phenylethyl)pyrrolidine-2-carboxylate
• CAS: 1262029-33-3
• 化学式: C₂₀H₂₂ClNO₂
• 分子量: 343.853
• InChiKey: KJFLZQZHCHRXJT-OYKVQYDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  L-脯氨酸甲酯盐酸盐 、 溴甲苯 、 2-氯苯甲醛 在 三氟乙酸 、 锌 作用下， 以 乙腈 为溶剂， 反应 3.17h， 以32%的产率得到(2S)-methyl 1-(1-(2-chlorophenyl)-2-phenylethyl)pyrrolidine-2-carboxylate
  参考文献：
  名称：

  Chiral amines in the diastereoselective Mannich-related multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines, and β-arylethylamines

  摘要：

  The multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines and beta-arylethylamines has been undergone starting from aryl- or benzylzinc reagents, aldehydes, and primary or secondary chiral amines. Good to high diastereoselectivities have been obtained from both L-proline ester derivatives 1 and (+/-)-trans-1-allyl-2,5-dimethylpiperazine (4). The use of R-(+)-1-phenylethylamine (7) provides important diastereoisomeric excesses (similar to 60%) in conjunction with very high chemical yields. This work constitutes a preliminary entry to the intended development of a more flexible reaction system, involving easily cleavable chiral amines. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.10.058

文献信息

• Chiral amines in the diastereoselective Mannich-related multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines, and β-arylethylamines
  作者：Caroline Haurena、Erwan LeGall、Stéphane Sengmany、Thierry Martens

  DOI：10.1016/j.tet.2010.10.058

  日期：2010.12

  The multicomponent synthesis of diarylmethylamines, 1,2-diarylethylamines and beta-arylethylamines has been undergone starting from aryl- or benzylzinc reagents, aldehydes, and primary or secondary chiral amines. Good to high diastereoselectivities have been obtained from both L-proline ester derivatives 1 and (+/-)-trans-1-allyl-2,5-dimethylpiperazine (4). The use of R-(+)-1-phenylethylamine (7) provides important diastereoisomeric excesses (similar to 60%) in conjunction with very high chemical yields. This work constitutes a preliminary entry to the intended development of a more flexible reaction system, involving easily cleavable chiral amines. (C) 2010 Elsevier Ltd. All rights reserved.