(1S,2S,3R,4S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-2,4-dimethyl-6-methylenecyclohexane-1,3-diol | 1377359-07-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1S,2S,3R,4S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-2,4-dimethyl-6-methylenecyclohexane-1,3-diol
• 英文别名: (1S,2S,3R,4S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-2,4-dimethyl-6-methylidenecyclohexane-1,3-diol
• CAS: 1377359-07-3
• 化学式: C₂₉H₄₈O₃
• 分子量: 444.698
• InChiKey: DEXRGRQRBRMFPA-RKGTZUQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S,2S,3S,4R)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethyl]-5-(benzenesulfonyl)-2,4-dimethyl-6-methylidenecyclohexane-1,3-diol 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以9.5 mg的产率得到(1S,2S,3R,4S,Z)-5-((E)-2-((1R,3aS,7aR)-1-((R)-6-hydroxy-6-methylheptan-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-ylidene)ethylidene)-2,4-dimethyl-6-methylenecyclohexane-1,3-diol
  参考文献：
  名称：

  Fluoride-Mediated Elimination of Allyl Sulfones: Application to the Synthesis of a 2,4-Dimethyl-A-ring Vitamin D₃ Analogue

  摘要：

  A coupling strategy for the synthesis of 2,4-dimethyl-1 alpha,25(OH)(2)D-3 is achieved which involves methylation of a pro-A ring vinyl sulfone and in situ traping of the allyl sulfonyl anion with a CD ring allyl chloride. TBAF-promoted 1,2-eliminative desulfonylation and concomitant silyl ether deprotection gives the vitamin D-3 analogue.

  DOI：

  10.1021/jo300672a