(1R,2R,3S,4R,6S)-6-Bromo-1-ethoxy-5-oxo-3-phenyl-bicyclo[2.2.2]octane-2-carboxylic acid ethyl ester | 133961-07-6

• 分子结构分类: 有机化合物
• 英文名称: (1R,2R,3S,4R,6S)-6-Bromo-1-ethoxy-5-oxo-3-phenyl-bicyclo[2.2.2]octane-2-carboxylic acid ethyl ester
• CAS: 133961-07-6
• 化学式: C₁₉H₂₃BrO₄
• 分子量: 395.293
• InChiKey: UPXVQVBXIBTRRP-LEVYEWFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4R,6S)-6-Bromo-1-ethoxy-5-oxo-3-phenyl-bicyclo[2.2.2]octane-2-carboxylic acid ethyl ester 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 以82%的产率得到(1R,2R,3S,4R,5R,6R)-6-Bromo-1-ethoxy-5-hydroxy-3-phenyl-bicyclo[2.2.2]octane-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Perkin communications. Stereochemistry of substituted 1-alkoxybicyclo[2.2.2]octenes; Diels–Alder synthesis versus Tandem-Michael strategy

  摘要：

  Diels-Alder reactions of 1-methoxy- and 1 -ethoxy-cyclohexa-1,3-?? dienes with ethyl cinnamate or ethyl 4,4,4-trifluorocrotonate favour the (1RS,2RS,3SR,4RS) (exo-carboxylate) bicyclo[2.2.2]octene stereochemistry, 5,6,9, whereas the bicyclo-octenes derived from 3-alkoxycyclohex-2-enones by Tandem-Michael additions are obtained exclusively as the (1RS,2SR,3RS,4RS) (endo-carboxylate) isomers 16.

  DOI：

  10.1039/p19910000651
• 作为产物：
  描述：

  反式-肉桂酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 lithium dicyclohexylamide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 生成 (1R,2R,3S,4R,6S)-6-Bromo-1-ethoxy-5-oxo-3-phenyl-bicyclo[2.2.2]octane-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Perkin communications. Stereochemistry of substituted 1-alkoxybicyclo[2.2.2]octenes; Diels–Alder synthesis versus Tandem-Michael strategy

  摘要：

  Diels-Alder reactions of 1-methoxy- and 1 -ethoxy-cyclohexa-1,3-?? dienes with ethyl cinnamate or ethyl 4,4,4-trifluorocrotonate favour the (1RS,2RS,3SR,4RS) (exo-carboxylate) bicyclo[2.2.2]octene stereochemistry, 5,6,9, whereas the bicyclo-octenes derived from 3-alkoxycyclohex-2-enones by Tandem-Michael additions are obtained exclusively as the (1RS,2SR,3RS,4RS) (endo-carboxylate) isomers 16.

  DOI：

  10.1039/p19910000651