methyl (1S,2R,4R)-N-benzoyl-2-hydroxymethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate | 685896-66-6

• 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: methyl (1S,2R,4R)-N-benzoyl-2-hydroxymethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
• 英文别名: methyl (1S,2R,4R)-7-benzoyl-2-(hydroxymethyl)-7-azabicyclo[2.2.1]heptane-1-carboxylate
• CAS: 685896-66-6
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: PTURNXDUCYMXSL-ZENOOKHLSA-N

物化性质

• 熔点：
  91-93 °C
• 沸点：
  446.4±20.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  methyl (1S,2R,4R)-N-benzoyl-2-hydroxymethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate 在 sodium hydride 、 三乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 147.0h， 生成 methyl (1S,2R,4R)-N-benzoyl-2-benzylthiomethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  New enantiopure 7-azanorbornane β-substituted prolines by SN2 displacements at the Cγ of the side chain

  摘要：

  Continuing our work on building new beta-substituted prolines in en antiomerically pure form as new surrogates to be incorporated into model peptides, we describe functional group conversions and carbon-carbon bond forming reactions by S(N)2 displacements at the gamma-position of the alpha-amino acid side chain of an azanorbornane derivative. This work extends efforts on the elaboration of the side arm at carbon C2 of the 7-azabicyclo[2.2.1]heptane core. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.003
• 作为产物：
  描述：

  methyl (1S,2R,4R)-N-benzoyl-2-formyl-7-azabicyclo[2.2.1]heptane-1-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.83h， 以97%的产率得到methyl (1S,2R,4R)-N-benzoyl-2-hydroxymethyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  New enantiopure 7-azanorbornane β-substituted prolines by SN2 displacements at the Cγ of the side chain

  摘要：

  Continuing our work on building new beta-substituted prolines in en antiomerically pure form as new surrogates to be incorporated into model peptides, we describe functional group conversions and carbon-carbon bond forming reactions by S(N)2 displacements at the gamma-position of the alpha-amino acid side chain of an azanorbornane derivative. This work extends efforts on the elaboration of the side arm at carbon C2 of the 7-azabicyclo[2.2.1]heptane core. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.003

文献信息

• Synthesis of enantiopure 7-azanorbornane proline–α-amino acid chimeras by highly efficient HPLC resolution of a phenylalanine analogue
  作者：Ana M. Gil、Elena Buñuel、Pilar López、Carlos Cativiela

  DOI：10.1016/j.tetasy.2003.12.008

  日期：2004.3

  4S)-2-phenyl-7-azabicyclo [2.2.1]heptane-1-carboxylic acid hydrochlorides, which are proline–phenylalanine chimeras, have been separately obtained by resolution of a key intermediate using chiral high performance liquid chromatography. The efficiency of the chromatographic resolution provides a general methodology for the preparation of both enantiomers of a broad variety of proline–α-amino acid chimeras with a

  对映体纯的构象受限的脯氨酸（1 S，2 S，4 R）-和（1 R，2 R，4 S）-2-苯基-7-氮杂双环[2.2.1]庚烷-1-羧酸盐酸盐，它们是脯氨酸-苯丙氨酸嵌合体，是通过使用手性高效液相色谱拆分关键中间体而单独获得的。色谱分离的效率为制备具有7-氮杂降硼烷骨架的多种脯氨酸-α-氨基酸嵌合体的两种对映异构体提供了一种对映体纯形式的通用方法。