Cyclopropanemethanol, a-hexyl-2,2,3-trimethyl- | 139131-64-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Cyclopropanemethanol, a-hexyl-2,2,3-trimethyl-
• 英文别名: 1-(cis-2,2,3-Trimethylcyclopropyl)-1-heptanol
• CAS: 139131-64-9；139238-84-9；139238-85-0
• 化学式: C₁₃H₂₆O
• 分子量: 198.349
• InChiKey: WDMLEHNMSUIUMC-PRWSFJOGSA-N

物化性质

• 沸点：
  244.7±8.0 °C(Predicted)
• 密度：
  0.872±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  Cyclopropanemethanol, a-hexyl-2,2,3-trimethyl- 在 水 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以85%的产率得到(E)-2,3-Dimethyl-4-undecen-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
• 作为产物：
  描述：

  庚醛 在 叔丁基锂 、 diethylzinc 作用下， 反应 58.53h， 生成 Cyclopropanemethanol, a-hexyl-2,2,3-trimethyl-
  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