(1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one | 139236-68-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one
• 英文别名: (1R,2R,3R,5S)-3-[tert-butyl(diphenyl)silyl]oxy-2-ethenylbicyclo[3.2.0]heptan-6-one
• CAS: 139236-68-3
• 化学式: C₂₅H₃₀O₂Si
• 分子量: 390.598
• InChiKey: OFBJJYVVYWAFBC-PIATZUFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one 在 双氧水 作用下， 以 2,2,2-三氟乙醇 为溶剂， 生成 (1S,5R,6R,7R)-7-(tert-butyldiphenylsilyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one 、 (3aS,5R,6R,6aR)-5-[tert-butyl(diphenyl)silyl]oxy-6-ethenyl-1,3a,4,5,6,6a-hexahydrocyclopenta[c]furan-3-one
  参考文献：
  名称：

  A short multigram asymmetric synthesis of prostanoid scaffolds

  摘要：

  Enantiomerically pure polysubstituted cyclopentanes which can be regarded as prostanoid scaffolds have been prepared by an efficient synthetic sequence readily applicable to the preparation of multigram quantities. The first key reaction is the diastereoselective allylmetallation of oxoamide 4 which is readily prepared from gamma-butyrolactone and an enantiomerically pure 2,5-dimethylpyrrolidine. The second key-step is an intramolecular [2+2] cycloaddition of a keteneiminium salt leading to bicylo[3.2.0] heptanones. These intermediates have been easily transformed into a variety of prostanoid scaffolds of high enantionneric purities. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00920-7
• 作为产物：
  描述：

  (2S,5S)-1-[(4R)-4-hydroxy-5-vinylhept-6-enoyl]-2,5-dimethylpyrrolidine 在 咪唑 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 101.0h， 生成 (1R,2R,3R,5S)-3-(tert-butyldiphenylsilyloxy)-2-vinyl-bicyclo[3.2.0]heptan-6-one
  参考文献：
  名称：

  A short multigram asymmetric synthesis of prostanoid scaffolds

  摘要：

  Enantiomerically pure polysubstituted cyclopentanes which can be regarded as prostanoid scaffolds have been prepared by an efficient synthetic sequence readily applicable to the preparation of multigram quantities. The first key reaction is the diastereoselective allylmetallation of oxoamide 4 which is readily prepared from gamma-butyrolactone and an enantiomerically pure 2,5-dimethylpyrrolidine. The second key-step is an intramolecular [2+2] cycloaddition of a keteneiminium salt leading to bicylo[3.2.0] heptanones. These intermediates have been easily transformed into a variety of prostanoid scaffolds of high enantionneric purities. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00920-7