1-(2-benzyloxycarbonylamino-3-methyl-1-oxo-4-pentenyl)-pyrrolidine

• 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: 1-(2-benzyloxycarbonylamino-3-methyl-1-oxo-4-pentenyl)-pyrrolidine
• 英文别名: benzyl N-[(2R,3S)-3-methyl-1-oxo-1-pyrrolidin-1-ylpent-4-en-2-yl]carbamate
• 化学式: C₁₈H₂₄N₂O₃
• 分子量: 316.4
• InChiKey: PDGUUMGUFSHDHJ-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  、 巴豆醇 在 正丁基锂 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(2-benzyloxycarbonylamino-3-methyl-1-oxo-4-pentenyl)-pyrrolidine 、 1-(2-benzyloxycarbonylamino-3-methyl-1-oxo-4-pentenyl)-pyrrolidine
  参考文献：
  名称：

  Synthesis of Anti-β-Substituted γ,δ-Unsaturated Amino Acids via Eschenmoser−Claisen Rearrangement

  摘要：

  Anti-beta-substituted gamma,delta-unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.

  DOI：

  10.1021/ol061414l

文献信息

• Synthesis of Anti-β-Substituted γ,δ-Unsaturated Amino Acids via Eschenmoser−Claisen Rearrangement
  作者：Hongchang Qu、Xuyuan Gu、Byoung J. Min、Zhihua Liu、Victor J. Hruby

  DOI：10.1021/ol061414l

  日期：2006.9

  Anti-beta-substituted gamma,delta-unsaturated amino acids have been synthesized via a novel design of the Eschenmoser-Claisen rearrangement. The rearrangement gives good isolated yields and excellent diastereoselectivity due to (Z)-N,O-ketene acetal formation and the pseudochairlike conformations of the reaction intermediates. Upon reductive hydrolysis, important novel amino acids and amino alcohols were synthesized for the first time via this methodology.