(1R,3aR,4S,7aR)-1-((E)-(R)-5-Hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-4-ol | 139131-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3aR,4S,7aR)-1-((E)-(R)-5-Hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-4-ol
• 英文别名: (1R,3aR,4S,7aR)-1-[(E,2R)-6-hydroxy-6-methylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-ol
• CAS: 139131-75-2
• 化学式: C₁₈H₃₂O₂
• 分子量: 280.451
• InChiKey: NNLIGWTYLHBKBZ-QNAFMVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,3aR,4S,7aR)-1-((E)-(R)-5-Hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-4-ol 在 pyridinium chlorochromate 作用下， 以57%的产率得到(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：

  <1R-<1β(R^*,E),3aα,4β,7aβ>>-6-(Octahydro-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7a-methyl-1H-inden-1-yl)-2-methyl-4-hepten-2-ol 在 氢氟酸 作用下， 以 乙腈 为溶剂， 以93%的产率得到(1R,3aR,4S,7aR)-1-((E)-(R)-5-Hydroxy-1,5-dimethyl-hex-2-enyl)-7a-methyl-octahydro-inden-4-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