(+)-(Z)-2-benzylidene-5(αS)-hydroxy-1-azabicyclo[2.2.2]octan-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 英文名称: (+)-(Z)-2-benzylidene-5(αS)-hydroxy-1-azabicyclo[2.2.2]octan-3-one
• 英文别名: (2Z,4R,5S)-2-benzylidene-5-hydroxy-1-azabicyclo[2.2.2]octan-3-one
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: JNKZJAPCZUBINF-KCWVNHISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one 在 Cunninghamella echinulata ATCC 9244 phosphate buffer 、 葡萄糖 、 二甲基亚砜 作用下， 反应 23.0h， 以17.9%的产率得到(α,α)-(Z)-2-benzylidene-5,7-dihydroxy-1-azabicyclo[2.2.2]octan-3-one
  参考文献：
  名称：

  Microbial hydroxylation of (Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one

  摘要：

  Microbial hydroxylation of (Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one 1 by various species of fungi and actinomycetes occurred regio- and stereoselectively at the 5 position of the quinuclidinone moiety. Most of the organisms produced alpha-(5S)-(Z)-2-benzylidene-5-hydroxy-1-azabicyclo[2.2.2]octan-3-one 2 as the major product with enantiomeric excesses ranging from 30% to 84%. The (5 beta)-hydroxy epimer 3 and the (5 alpha,7 alpha)-dihydroxy derivative 4 were also produced by whole cell biotransformations of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00471-1

文献信息

• Microbial hydroxylation of (Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one
  作者：John W. Wong、Michael P. Burns

  DOI：10.1016/s0957-4166(99)00471-1

  日期：1999.11

  Microbial hydroxylation of (Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one 1 by various species of fungi and actinomycetes occurred regio- and stereoselectively at the 5 position of the quinuclidinone moiety. Most of the organisms produced alpha-(5S)-(Z)-2-benzylidene-5-hydroxy-1-azabicyclo[2.2.2]octan-3-one 2 as the major product with enantiomeric excesses ranging from 30% to 84%. The (5 beta)-hydroxy epimer 3 and the (5 alpha,7 alpha)-dihydroxy derivative 4 were also produced by whole cell biotransformations of 1. (C) 1999 Elsevier Science Ltd. All rights reserved.