(2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester | 252847-74-8

• 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: (2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester
• 英文别名: methyl (3R,4S,6R)-6-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-3-carboxylate
• CAS: 252847-74-8
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: KEAYTRQQDQHWJM-YIZRAAEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester 在 4-二甲氨基吡啶 、 二甲基氯化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Novel Bridged Bicyclic α-Amino Acid Esters and Key Derivatives from Quincorine and Quincoridine

  摘要：

  Oxidation of Quincorine (QCl) and Quincoridine (QCD) has been investigated, giving bicyclic a-amino acids and dicarboxylic acid derivatives, which are epimerically and also enantiomerically pure. Acidic Cr(VI)-mediated oxidation (Jones oxidation) has been optimized with respect to reaction conduct and work up (addition of ethylenediamine).

  DOI：

  10.1021/ol990981o
• 作为产物：
  描述：

  甲醇 、 quincoridine 在 potassium permanganate 、 硫酸 、 盐酸 作用下， 以 水 为溶剂， 反应 125.0h， 以57%的产率得到(2R,4S,5R)-2-(hydroxymethyl)-1-azabicyclo[2.2.2]octane-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Novel Bridged Bicyclic α-Amino Acid Esters and Key Derivatives from Quincorine and Quincoridine

  摘要：

  Oxidation of Quincorine (QCl) and Quincoridine (QCD) has been investigated, giving bicyclic a-amino acids and dicarboxylic acid derivatives, which are epimerically and also enantiomerically pure. Acidic Cr(VI)-mediated oxidation (Jones oxidation) has been optimized with respect to reaction conduct and work up (addition of ethylenediamine).

  DOI：

  10.1021/ol990981o

文献信息

• Novel Bridged Bicyclic α-Amino Acid Esters and Key Derivatives from Quincorine and Quincoridine
  作者：Olaf Schrake、Volker S. Rahn、Jens Frackenpohl、Wilfried M. Braje、H. Martin R. Hoffmann

  DOI：10.1021/ol990981o

  日期：1999.11.1

  Oxidation of Quincorine (QCl) and Quincoridine (QCD) has been investigated, giving bicyclic a-amino acids and dicarboxylic acid derivatives, which are epimerically and also enantiomerically pure. Acidic Cr(VI)-mediated oxidation (Jones oxidation) has been optimized with respect to reaction conduct and work up (addition of ethylenediamine).