(4aS,7S,7aR)-7-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-methyl-7a-vinylhexahydrocyclopenta[d][1,3]dioxin-2-one | 1246189-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (4aS,7S,7aR)-7-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-methyl-7a-vinylhexahydrocyclopenta[d][1,3]dioxin-2-one
• 英文别名: (4aS,7S,7aR)-7-[3-[tert-butyl(dimethyl)silyl]oxypropyl]-7a-ethenyl-7-methyl-4,4a,5,6-tetrahydrocyclopenta[d][1,3]dioxin-2-one
• CAS: 1246189-49-0
• 化学式: C₁₉H₃₄O₄Si
• 分子量: 354.562
• InChiKey: PGUAQIDWDOPGCD-KFKAGJAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4aS,7S,7aR)-7-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-methyl-7a-vinylhexahydrocyclopenta[d][1,3]dioxin-2-one 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  A stereoselective cyclisation cascade mediated by SmI2–H2O: synthetic studies towards stolonidiol

  摘要：

  A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemo-selective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.047
• 作为产物：
  描述：

  三光气 、 (1R,2S,5S)-2-(3-((tert-butyldimethylsilyl)oxy)propyl)-5-(hydroxymethyl)-2-methyl-1-vinylcyclopentanol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以71.6 mg的产率得到(4aS,7S,7aR)-7-(3-((tert-butyldimethylsilyl)oxy)propyl)-7-methyl-7a-vinylhexahydrocyclopenta[d][1,3]dioxin-2-one
  参考文献：
  名称：

  A stereoselective cyclisation cascade mediated by SmI2–H2O: synthetic studies towards stolonidiol

  摘要：

  A cascade reaction involving sequential conjugate reduction, stereoselective aldol cyclisation and chemo-selective lactone reduction mediated by SmI2-H2O provides access to a cyclopentanol bearing two vicinal quaternary stereocentres with good stereocontrol. The functionalised cyclopentanol product has been converted to a key intermediate in ongoing asymmetric studies towards stolonidiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.047