3-(tert-butoxycarbonyl)-3-azabicyclo[4.1.0]heptane-1-carboxylic acid | 1239421-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(tert-butoxycarbonyl)-3-azabicyclo[4.1.0]heptane-1-carboxylic acid
• 英文别名: 3-tert-butyl 3-aza-bicyclo[4.1.0]heptane-1,3-dicarboxylate；3-(Tert-butoxycarbonyl)-3-azabicyclo[4.1.0]heptane-1-carboxylic acid；3-[(2-methylpropan-2-yl)oxycarbonyl]-3-azabicyclo[4.1.0]heptane-1-carboxylic acid
• CAS: 1239421-67-0
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: BKMZZZVRNHEHLG-UHFFFAOYSA-N

物化性质

• 沸点：
  363.3±25.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(tert-butoxycarbonyl)-3-azabicyclo[4.1.0]heptane-1-carboxylic acid 在 盐酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 以96%的产率得到3-氮杂双环[4.1.0]庚烷-1-羧酸盐酸盐
  参考文献：
  名称：

  Synthesis of racemic and enantiopure 3,4-methanonipecotic acid

  摘要：

  The synthesis of both racemic and enantiomerically pure (1R,6S)-3,4-methanonipecotic acid, a cyclopropane-containing 8-amino acid, which is a valuable building block for drug discovery, is described. The synthetic scheme commences from natural (S)-malic acid and allows for the preparation of the title compound in 12 steps in 28% overall yield. A novel approach to the racemic 3,4-methanonipecotic acid, which relies on a Simmons-Smith cyclopropanation as the key step, was also developed. In this case, the product was obtained in 8 steps and 38% total yield. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2015.09.015
• 作为产物：
  描述：

  (3-苄基-3-氮杂双环[4.1.0]庚-1-基)甲醇 在 sodium chlorite 、 disodium hydrogenphosphate 、 2-甲基-2-丁烯 、 palladium 10% on activated carbon 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 50.0 ℃ 、7.0 MPa 条件下， 反应 72.0h， 生成 3-(tert-butoxycarbonyl)-3-azabicyclo[4.1.0]heptane-1-carboxylic acid
  参考文献：
  名称：

  Synthesis of racemic and enantiopure 3,4-methanonipecotic acid

  摘要：

  The synthesis of both racemic and enantiomerically pure (1R,6S)-3,4-methanonipecotic acid, a cyclopropane-containing 8-amino acid, which is a valuable building block for drug discovery, is described. The synthetic scheme commences from natural (S)-malic acid and allows for the preparation of the title compound in 12 steps in 28% overall yield. A novel approach to the racemic 3,4-methanonipecotic acid, which relies on a Simmons-Smith cyclopropanation as the key step, was also developed. In this case, the product was obtained in 8 steps and 38% total yield. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2015.09.015

文献信息

• Synthesis of 3-azabicyclo[4.1.0]heptane-1-carboxylic acid
  作者：Carmela Napolitano、Manuela Borriello、Francesca Cardullo、Daniele Donati、Alfredo Paio、Stefano Manfredini

  DOI：10.1016/j.tet.2010.05.006

  日期：2010.7

  A full study on the synthesis of 3-azabicyclo[4.1.0]heptane-1-carboxylic acid is described. Three different approaches were investigated in order to achieve an efficient synthesis of this unnatural aminoacid. The optimized synthetic route relies upon three key steps: (i) diazomalonate insertion on 4-phtalimido 1-butene, (ii) intramolecular cyclization and (iii) chemoselective reduction of the resulting

  描述了对3-氮杂双环[4.1.0]庚烷-1-羧酸的合成的全面研究。为了实现这种非天然氨基酸的有效合成，研究了三种不同的方法。优化的合成路线取决于三个关键步骤：（i）将重氮丙二酸酯插入4-phtalimido 1-butene，（ii）分子内环化和（iii）产生的内酰胺的化学选择性还原。由于其双环性质和构象限制，这种氨基酸可能是药物化学中有用的组成部分。
• Synthesis of racemic and enantiopure 3,4-methanonipecotic acid
  作者：Andriy V. Tymtsunik、Yevhen M. Ivon、Igor V. Komarov、Oleksandr O. Grygorenko

  DOI：10.1016/j.tetasy.2015.09.015

  日期：2015.12

  The synthesis of both racemic and enantiomerically pure (1R,6S)-3,4-methanonipecotic acid, a cyclopropane-containing 8-amino acid, which is a valuable building block for drug discovery, is described. The synthetic scheme commences from natural (S)-malic acid and allows for the preparation of the title compound in 12 steps in 28% overall yield. A novel approach to the racemic 3,4-methanonipecotic acid, which relies on a Simmons-Smith cyclopropanation as the key step, was also developed. In this case, the product was obtained in 8 steps and 38% total yield. (C) 2015 Published by Elsevier Ltd.