(1S,5R,6R,7R)-7-(tert-butyldiphenylsilyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one | 387354-46-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1S,5R,6R,7R)-7-(tert-butyldiphenylsilyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one
• 英文别名: (3aR,4R,5R,6aS)-5-[tert-butyl(diphenyl)silyl]oxy-4-ethenyl-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 387354-46-3
• 化学式: C₂₅H₃₀O₃Si
• 分子量: 406.597
• InChiKey: TWSGRFQCGHFJHM-BXXSPATCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  29
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,5R,6R,7R)-7-(tert-butyldiphenylsilyloxy)-6-vinyl-2-oxabicyclo[3.3.0]octan-3-one 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到(1S,5R,6R,7R)-7-(tert-butyldiphenylsilyloxy)-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-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：

  (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