(4aS,5S,7S,8S,9aR)-8-methyl-3-oxodecahydro-5,8-epoxy-7,9a-methanobenzo[7]annulen-2-yl methanesulfonate | 1256640-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (4aS,5S,7S,8S,9aR)-8-methyl-3-oxodecahydro-5,8-epoxy-7,9a-methanobenzo[7]annulen-2-yl methanesulfonate
• CAS: 1256640-15-9
• 化学式: C₁₄H₂₀O₅S
• 分子量: 300.376
• InChiKey: IYSPDTDYOOMKBN-PCKVIHQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4aS,5S,7S,8S,9aR)-8-methyl-3-oxodecahydro-5,8-epoxy-7,9a-methanobenzo[7]annulen-2-yl methanesulfonate 在 lithium bromide monohydrate 、 lithium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以12 mg的产率得到(1S,6S,7S,9S,10S)-9-methyl-8-oxatetracyclo[7.2.1.17,10.01,6]tridec-2-en-4-one
  参考文献：
  名称：

  A Bismuth(III)-Catalyzed Friedel−Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (−)-Platensimycin

  摘要：

  A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

  DOI：

  10.1021/ol102390t
• 作为产物：
  描述：

  (1S,7S,9S,10S)-3-methoxy-9-methyl-8-oxatetracyclo[7.2.1.17,10.01,6]trideca-2,5-dien-4-one 在 aluminum (III) chloride 、 二氢吡啶 、 tert-butyl (2R)-2-amino-3-phenylpropanoate;2,2,2-trifluoroacetic acid 、 四丁基碘化铵 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 生成 (4aS,5S,7S,8S,9aR)-8-methyl-3-oxodecahydro-5,8-epoxy-7,9a-methanobenzo[7]annulen-2-yl methanesulfonate
  参考文献：
  名称：

  A Bismuth(III)-Catalyzed Friedel−Crafts Cyclization and Stereocontrolled Organocatalytic Approach to (−)-Platensimycin

  摘要：

  A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO4 to suppress the Lewis basicity of the sulfonate group. After TBAF-promotecl cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.

  DOI：

  10.1021/ol102390t