(2R,3R,6S,7R)-3,6-epoxy-10,10-dimethyl-8-oxo-2,7-methano-2,3,5,6,7,9,10,11-octahydro-8H-1,4-benzodioxonin-2-yl methanesulfonate | 1567840-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,3R,6S,7R)-3,6-epoxy-10,10-dimethyl-8-oxo-2,7-methano-2,3,5,6,7,9,10,11-octahydro-8H-1,4-benzodioxonin-2-yl methanesulfonate
• CAS: 1567840-20-3
• 化学式: C₁₅H₂₀O₇S
• 分子量: 344.386
• InChiKey: WEHYTSMYCGSLLT-XMUUBJLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,6S,7R)-3,6-epoxy-10,10-dimethyl-8-oxo-2,7-methano-2,3,5,6,7,9,10,11-octahydro-8H-1,4-benzodioxonin-2-yl methanesulfonate 在 sodium tetrahydroborate 、 nickel chloride hexahydrate 作用下， 以 乙醇 为溶剂， 以80%的产率得到(1S,2R,5R)-2-(4,4-dimethyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxabicyclo[3.2.1]octan-4-one
  参考文献：
  名称：

  Eleuthesides and their analogs: V. Medium- and large-ring lactones based on levoglucosenone

  摘要：

  Ozonolysis of the bridging double bond in bicyclic enol ethers obtained by the Michael reaction and subsequent intramolecular etherification afforded chiral decanolides fused to a tetrahydropyran ring. Three-step procedures were developed for the synthesis of chiral lactones with medium and large rings via oxidative cleavage with pyridinium chlorochromate of mixed bicyclic ketals which were prepared by treatment with methanolic HCl of Michael adducts derived from levoglucosenone and cyclopenta-, cyclohexa-, cyclohepta-, and cyclododecanone.

  DOI：

  10.1134/s1070428014010229
• 作为产物：
  描述：

  左旋葡萄糖酮 在 4-二甲氨基吡啶 、 二环己烷并-18-冠醚-6 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 (2R,3R,6S,7R)-3,6-epoxy-10,10-dimethyl-8-oxo-2,7-methano-2,3,5,6,7,9,10,11-octahydro-8H-1,4-benzodioxonin-2-yl methanesulfonate
  参考文献：
  名称：

  Eleuthesides and their analogs: V. Medium- and large-ring lactones based on levoglucosenone

  摘要：

  Ozonolysis of the bridging double bond in bicyclic enol ethers obtained by the Michael reaction and subsequent intramolecular etherification afforded chiral decanolides fused to a tetrahydropyran ring. Three-step procedures were developed for the synthesis of chiral lactones with medium and large rings via oxidative cleavage with pyridinium chlorochromate of mixed bicyclic ketals which were prepared by treatment with methanolic HCl of Michael adducts derived from levoglucosenone and cyclopenta-, cyclohexa-, cyclohepta-, and cyclododecanone.

  DOI：

  10.1134/s1070428014010229