(1S,3R)-benzyl 3-(benzyloxycarbonylamino)-2,2,3-trimethylcyclopentanecarboxylate

• 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: (1S,3R)-benzyl 3-(benzyloxycarbonylamino)-2,2,3-trimethylcyclopentanecarboxylate
• 英文别名: benzyl (1S,3R)-2,2,3-trimethyl-3-(phenylmethoxycarbonylamino)cyclopentane-1-carboxylate
• 化学式: C₂₄H₂₉NO₄
• 分子量: 395.499
• InChiKey: XOFXXXRMOIDAQQ-HYBUGGRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3R)-benzyl 3-(benzyloxycarbonylamino)-2,2,3-trimethylcyclopentanecarboxylate 在 1% Pd/C 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以72%的产率得到(1R,3S)-3-amino-2,2,3-trimethylcyclopentanecarboxylic acid
  参考文献：
  名称：

  Synthesis of d-camphor based γ-amino acid (1S,3R)-3-amino-2,2,3-trimethylcyclopentane carboxylic acid

  摘要：

  Synthesis of a gamma-amino acid derived from (1R,3S)-camphoric acid is described. D-(+)-Camphoric anhydride, prepared from D-(+)-camphoric acid by treatment with methanesulfonyl chloride and triethylamine, was reacted with benzyl alcohol and catalytic DMAP, and subsequently reacted in a Curtius rearrangement to afford the corresponding carbamate derivative. This derivative was converted to the desired gamma-amino acid through hydrogenolysis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.022
• 作为产物：
  描述：

  (1R,3S)-(+)-樟脑酐 、 苯甲醇 在 4-二甲氨基吡啶 、 三乙胺 、 叠氮磷酸二苯酯 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以43%的产率得到(1S,3R)-benzyl 3-(benzyloxycarbonylamino)-2,2,3-trimethylcyclopentanecarboxylate
  参考文献：
  名称：

  Synthesis of d-camphor based γ-amino acid (1S,3R)-3-amino-2,2,3-trimethylcyclopentane carboxylic acid

  摘要：

  Synthesis of a gamma-amino acid derived from (1R,3S)-camphoric acid is described. D-(+)-Camphoric anhydride, prepared from D-(+)-camphoric acid by treatment with methanesulfonyl chloride and triethylamine, was reacted with benzyl alcohol and catalytic DMAP, and subsequently reacted in a Curtius rearrangement to afford the corresponding carbamate derivative. This derivative was converted to the desired gamma-amino acid through hydrogenolysis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.022

文献信息

• Synthesis of d-camphor based γ-amino acid (1S,3R)-3-amino-2,2,3-trimethylcyclopentane carboxylic acid
  作者：Joel B. Eagles、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2010.03.022

  日期：2010.3

  Synthesis of a gamma-amino acid derived from (1R,3S)-camphoric acid is described. D-(+)-Camphoric anhydride, prepared from D-(+)-camphoric acid by treatment with methanesulfonyl chloride and triethylamine, was reacted with benzyl alcohol and catalytic DMAP, and subsequently reacted in a Curtius rearrangement to afford the corresponding carbamate derivative. This derivative was converted to the desired gamma-amino acid through hydrogenolysis. (C) 2010 Elsevier Ltd. All rights reserved.