(1S,2S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol | 133520-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol
• 英文别名: (1S,2S,4R,7S)-7-(phenylmethoxymethyl)bicyclo[2.2.1]hept-5-en-2-ol
• CAS: 133520-34-0
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: KKVPWJXBLONPNZ-AJNGGQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol 生成 7-Benzyloxymethylbicyclo<2.2.1>hept-5-en-2-one 、 (1S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-one
  参考文献：
  名称：

  Asymmetric microbiological baeyer-villiger reaction of a bridged bicyclic ketone: divergent behaviour of its enantiomers

  摘要：

  The bioconversion of 7-anti-benzyloxymethylbicyclo [2.2.1]hept-5-en-2-one 1 with cells of Acinetobacter calcoaceticus NCIB 9871 has been studied. Its (1R, 4S, 7R) enantiomer underwent a Baeyer-Villiger oxidation yielding rearranged lactone 2 (ee 85%), whereas (1S, 4R, 7S)-1 was reduced to alcohols 3-endo (ee 95%) and 3-exo (o.p. 89%).

  DOI：

  10.1016/s0040-4039(00)79478-0
• 作为产物：
  描述：

  7-Benzyloxymethylbicyclo<2.2.1>hept-5-en-2-one 在 特普 作用下， 生成 (3aR,4S,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydrocyclopenta[b]furan-2-one 、 (1S,2S,4R,7S)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol 、 (3aS,4R,6aR)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 、 (1R,2R,4S,7R)-7-Benzyloxymethyl-bicyclo[2.2.1]hept-5-en-2-ol
  参考文献：
  名称：

  Asymmetric microbiological baeyer-villiger reaction of a bridged bicyclic ketone: divergent behaviour of its enantiomers

  摘要：

  The bioconversion of 7-anti-benzyloxymethylbicyclo [2.2.1]hept-5-en-2-one 1 with cells of Acinetobacter calcoaceticus NCIB 9871 has been studied. Its (1R, 4S, 7R) enantiomer underwent a Baeyer-Villiger oxidation yielding rearranged lactone 2 (ee 85%), whereas (1S, 4R, 7S)-1 was reduced to alcohols 3-endo (ee 95%) and 3-exo (o.p. 89%).

  DOI：

  10.1016/s0040-4039(00)79478-0