(Benzyl-but-3-enyl-amino)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester | 186586-63-0

• 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: (Benzyl-but-3-enyl-amino)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS: 186586-63-0
• 化学式: C₂₉H₃₉NO₂
• 分子量: 433.634
• InChiKey: FSKKYYVEHVBBTH-XSBVVTFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.39
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Benzyl-but-3-enyl-amino)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 在 ammonium chloride 、 zinc dibromide 、 lithium diisopropyl amide 作用下， 生成 (2S,3R)-1-Benzyl-3-methyl-pyrrolidine-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 、 (2S,3S)-1-Benzyl-3-methyl-pyrrolidine-2-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl 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
• 作为产物：
  描述：

  N-苄基甘氨酸乙酯 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 192.0h， 生成 (Benzyl-but-3-enyl-amino)-acetic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl 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