6''-dihydro-12S,13R-epoxy-6''-O-(tert-butyldiphenylsilyl)niddanolide | 143317-68-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 6''-dihydro-12S,13R-epoxy-6''-O-(tert-butyldiphenylsilyl)niddanolide
• CAS: 143317-68-4
• 化学式: C₃₆H₅₀O₈Si
• 分子量: 638.874
• InChiKey: YNVVFGVPLNLJMV-GKQMZOHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  45.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  114.82
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-甲氧基丙烯 、 6''-dihydro-12S,13R-epoxy-6''-O-(tert-butyldiphenylsilyl)niddanolide 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以84%的产率得到6''-dihydro-12S,13R-epoxy-3,5-isopropylidene-6''-O-(tert-butyldiphenylsilyl)niddanolide
  参考文献：
  名称：

  Conformational analysis of the 16-membered epoxyenone and complete stereoselection in the reduction of its C9 carbonyl group, the key reaction in the synthesis of maridonolides

  摘要：

  16-membered epoxyenone (2), the key synthetic intermediate of maridonolides, has two distinct conformational isomers in solution. The conformational analysis of them by virtue of NMR measurement and the profound effect of their conformations on reactivity and stereoselectivity in the reduction of the C9 carbonyl group are discussed.

  DOI：

  10.1016/s0040-4020(01)81225-4
• 作为产物：
  描述：

  (11E,13E)-(4R,5S,6S,7R,9R,16R)-7-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,6-dihydroxy-5-methoxy-9,16-dimethyl-oxacyclohexadeca-11,13-diene-2,10-dione 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 以51%的产率得到6''-dihydro-12S,13R-epoxy-6''-O-(tert-butyldiphenylsilyl)niddanolide
  参考文献：
  名称：

  Conformational analysis of the 16-membered epoxyenone and complete stereoselection in the reduction of its C9 carbonyl group, the key reaction in the synthesis of maridonolides

  摘要：

  16-membered epoxyenone (2), the key synthetic intermediate of maridonolides, has two distinct conformational isomers in solution. The conformational analysis of them by virtue of NMR measurement and the profound effect of their conformations on reactivity and stereoselectivity in the reduction of the C9 carbonyl group are discussed.

  DOI：

  10.1016/s0040-4020(01)81225-4