2-(2-Chloro-pyrimidin-5-yl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-(2-Chloro-pyrimidin-5-yl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 2-(2-chloropyrimidin-5-yl)-7-azabicyclo[2.2.1]heptane-7-carboxylate；tert-butyl 2-(2-chloropyrimidin-5-yl)-7-azabicyclo[2.2.1]heptane-7-carboxylate
• 化学式: C₁₅H₂₀ClN₃O₂
• 分子量: 309.796
• InChiKey: ANWMQJXCXHPOGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-Chloro-pyrimidin-5-yl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以100%的产率得到2-(2-Chloro-pyrimidin-5-yl)-7-aza-bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Syntheses and biological properties of cysteine-Reactive epibatidine derivatives

  摘要：

  The synthesis of epibatidine derivatives modified at the 2-position of the pyridine or pyrimidine rings by reactive functions are described for potential irreversible site-directed coupling reactions on cysteine mutants of neuronal nicotinic acetylcholine receptors. An improved synthesis of the 7-azabicyclo[2,2,1]hepta-2,5-diene key intermediate has been developed to allow reproducible syntheses of the epibatidine derivatives. Binding tests and electrophysiological experiments allowed to select the 2-substituted alpha-chloroacetamido 13 and the chloropyrimidine derivative 11 as potential site-directed probes for the epibatidine binding site. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00092-1
• 作为产物：
  描述：

  endo-2-(p-tolyl-sulfone)-7-tert-butoxycarbonyl-7-azabicyclo<2.2.1>hept-2-ene 在 甲醇 、 sodium amalgam 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-(2-Chloro-pyrimidin-5-yl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Syntheses and biological properties of cysteine-Reactive epibatidine derivatives

  摘要：

  The synthesis of epibatidine derivatives modified at the 2-position of the pyridine or pyrimidine rings by reactive functions are described for potential irreversible site-directed coupling reactions on cysteine mutants of neuronal nicotinic acetylcholine receptors. An improved synthesis of the 7-azabicyclo[2,2,1]hepta-2,5-diene key intermediate has been developed to allow reproducible syntheses of the epibatidine derivatives. Binding tests and electrophysiological experiments allowed to select the 2-substituted alpha-chloroacetamido 13 and the chloropyrimidine derivative 11 as potential site-directed probes for the epibatidine binding site. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00092-1

文献信息

• Syntheses and biological properties of cysteine-Reactive epibatidine derivatives
  作者：Christian Che、Grégory Petit、Florence Kotzyba-Hibert、Sonia Bertrand、Daniel Bertrand、Thomas Grutter、Maurice Goeldner

  DOI：10.1016/s0960-894x(03)00092-1

  日期：2003.3

  The synthesis of epibatidine derivatives modified at the 2-position of the pyridine or pyrimidine rings by reactive functions are described for potential irreversible site-directed coupling reactions on cysteine mutants of neuronal nicotinic acetylcholine receptors. An improved synthesis of the 7-azabicyclo[2,2,1]hepta-2,5-diene key intermediate has been developed to allow reproducible syntheses of the epibatidine derivatives. Binding tests and electrophysiological experiments allowed to select the 2-substituted alpha-chloroacetamido 13 and the chloropyrimidine derivative 11 as potential site-directed probes for the epibatidine binding site. (C) 2003 Elsevier Science Ltd. All rights reserved.