<1R-<1β,<αS*,βS*>,3aα,4aβ,7aβ>>-Octahydro-β,7a-dimethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-(2',2'-dimethyl-1-ethenyl)-1H-indene-1-ethanol | 139131-72-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: <1R-<1β,<αS*,βS*>,3aα,4aβ,7aβ>>-Octahydro-β,7a-dimethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-(2',2'-dimethyl-1-ethenyl)-1H-indene-1-ethanol
• 英文别名: <1R-<1β,<αS^*,βS^*>,3aα,4aβ,7aβ>>-Octahydro-β,7a-dimethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-(2',2'-dimethyl-1-ethenyl)-1H-indene-1-ethanol；[1R-(1β,[αS^*,βS^*],3aα,4aβ,7aβ)]-Octahydro-β,7a-dimethyl-4-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-α-(2',2'-dimethyl-1-ethenyl)-1H-indene-1-ethanol
• CAS: 139131-72-9；139238-90-7
• 化学式: C₂₃H₄₄O₂Si
• 分子量: 380.687
• InChiKey: ULVLBJAVXVZMRP-CGFLSKIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 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,<αS*,βS*>,3aα,4aβ,7aβ>>-Octahydro-β,7a-dimethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-(2',2'-dimethyl-1-ethenyl)-1H-indene-1-ethanol 在 氢氟酸 、 水 、 diethylzinc 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 (1R,3aR,7aR)-1-((E)-(R)-5-Hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-4-one
  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：

  1-溴-2-甲基-1-丙烯 、 (S)-2-[(1R,3aR,4S,7aR)-octahydro-4-[(1,1-dimethylethyl)dimethylsilyloxy]-7a-methyl-1H-inden-1-yl]propanal 在 叔丁基锂 作用下， 生成 <1R-<1β,<αS*,βS*>,3aα,4aβ,7aβ>>-Octahydro-β,7a-dimethyl-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-(2',2'-dimethyl-1-ethenyl)-1H-indene-1-ethanol
  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