<1R<1β(R^*,E,S^*),3aα,4β,7aβ>>-6-(Octahydro-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7a-methyl-1H-inden-1-yl)-2,3-dimethyl-4-hepten-2-ol | 139238-87-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: <1R<1β(R^*,E,S^*),3aα,4β,7aβ>>-6-(Octahydro-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7a-methyl-1H-inden-1-yl)-2,3-dimethyl-4-hepten-2-ol
• 英文别名: (E,3S,6R)-6-[(1R,3aR,4S,7aR)-4-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]-2,3-dimethylhept-4-en-2-ol
• CAS: 139238-87-2
• 化学式: C₂₅H₄₈O₂Si
• 分子量: 408.74
• InChiKey: VCTXSFGHAZDFQZ-CCMNTYHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  <1R<1β(R^*,E,S^*),3aα,4β,7aβ>>-6-(Octahydro-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7a-methyl-1H-inden-1-yl)-2,3-dimethyl-4-hepten-2-ol 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以95%的产率得到帕立骨化醇杂质A01
  参考文献：
  名称：

  Two new approaches to the 25-hydroxy-vitamin D2 side chain

  摘要：

  Two approaches to the 25-hydroxy-vitamin D2 side chain have been developed based on the solvolysis of cyclopropylcarbinyl precursors. The first involves addition of trimethylcyclopropyllithium reagent 4 to a suitably protected C/D system 9. This reaction leads directly to cyclopropylcarbinols 10a,b which can be solvolyzed to the vitamin D2 side chain directly. The second approach uses an intermediate C/D system with a side chain allylic alcohol. Cyclopropanation of the allylic alcohol using Et2Zn/CH3CHI2 produces the same type of cyclopropylcarbinols 10a,b but in differing isomer ratios. Model studies and stereochemical differences in the two approaches are discussed.

  DOI：

  10.1021/jo00033a021
• 作为产物：
  描述：

  (S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal 在 四甲基乙二胺 、 水 、 叔丁基锂 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 <1R<1β(R^*,E,S^*),3aα,4β,7aβ>>-6-(Octahydro-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7a-methyl-1H-inden-1-yl)-2,3-dimethyl-4-hepten-2-ol
  参考文献：
  名称：

  Two new approaches to the 25-hydroxy-vitamin D2 side chain

  摘要：

  Two approaches to the 25-hydroxy-vitamin D2 side chain have been developed based on the solvolysis of cyclopropylcarbinyl precursors. The first involves addition of trimethylcyclopropyllithium reagent 4 to a suitably protected C/D system 9. This reaction leads directly to cyclopropylcarbinols 10a,b which can be solvolyzed to the vitamin D2 side chain directly. The second approach uses an intermediate C/D system with a side chain allylic alcohol. Cyclopropanation of the allylic alcohol using Et2Zn/CH3CHI2 produces the same type of cyclopropylcarbinols 10a,b but in differing isomer ratios. Model studies and stereochemical differences in the two approaches are discussed.

  DOI：

  10.1021/jo00033a021