(2S,3R)-3-Methyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester | 186586-70-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-3-Methyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester
• 英文别名: ethyl (2S,3R)-3-methyl-1-[(1S)-1-phenylethyl]pyrrolidine-2-carboxylate
• CAS: 186586-70-9
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: BNQJEVAPVOQCOQ-IPYPFGDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-Methyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 生成 乙基(3R)-3-甲基-L-脯氨酸酯
  参考文献：
  名称：

  New strategy for the synthesis of 3-substituted prolines

  摘要：

  Ring formation involving a Sere trig cyclization between a zinc enolate and a non activated double bond led to cis diastereoisomer of 3-substituted prolines. This cyclization was achieved with transfer of chirality onto the C-2 carbon when nitrogen was protected by an alpha-methylbenzyl group. Reprotonation of the lithium enolate of cis derivative yielded the trans diastereoisomer. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02221-6
• 作为产物：
  描述：

  (S)-2-(1-苯基乙氨基)乙酸乙酯 在 ammonium chloride 、 三乙胺 、 zinc dibromide 、 lithium diisopropyl amide 作用下， 以 二甲基亚砜 为溶剂， 反应 192.33h， 生成 (2S,3R)-3-Methyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  New strategy for the synthesis of 3-substituted prolines

  摘要：

  Ring formation involving a Sere trig cyclization between a zinc enolate and a non activated double bond led to cis diastereoisomer of 3-substituted prolines. This cyclization was achieved with transfer of chirality onto the C-2 carbon when nitrogen was protected by an alpha-methylbenzyl group. Reprotonation of the lithium enolate of cis derivative yielded the trans diastereoisomer. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02221-6

文献信息

• Development of a Zinc-Mediated Approach to a 2,3-<i>cis</i>-Pyrrolidine Arginase Inhibitor
  作者：Thomas W. Lyons、Theodore A. Martinot、Cyndi Qixin He、Ji Qi、Guangxin Shao

  DOI：10.1021/acs.oprd.0c00171

  日期：2020.8.21

  This manuscript outlines the development activities toward a robust synthesis of cis-2,3-pyrrolidine via tandem zincenolate cyclization/Negishi coupling that proceeds with high diastereoselectivity. The methodology facilitated a gram-scale delivery of the target API and eliminated the need for costly chiral resolutions and inefficient protecting group manipulations. A series of DFT experiments provided a transition-state model that agrees closely with the experimental observations and provides a more in-depth understanding of the observed selectivity.
• New strategy for the synthesis of 3-substituted prolines
  作者：Philippe Karoyan、Gérard Chassaing

  DOI：10.1016/s0040-4039(96)02221-6

  日期：1997.1

  Ring formation involving a Sere trig cyclization between a zinc enolate and a non activated double bond led to cis diastereoisomer of 3-substituted prolines. This cyclization was achieved with transfer of chirality onto the C-2 carbon when nitrogen was protected by an alpha-methylbenzyl group. Reprotonation of the lithium enolate of cis derivative yielded the trans diastereoisomer. Copyright (C) 1996 Published by Elsevier Science Ltd