1-(2,2-二甲基环丙基)-1-庚醇 | 139131-71-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 1-(2,2-二甲基环丙基)-1-庚醇
• 中文别名: 环丙甲醇,a-己基-2,2-二甲基-
• 英文名称: 1-(2,2-Dimethylcyclopropyl)-1-heptanol
• 英文别名: 1-(2,2-Dimethylcyclopropyl)heptan-1-ol
• CAS: 139131-71-8
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: FBWSTRLSXNTWEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2,2-二甲基环丙基)-1-庚醇 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76%的产率得到trans-2-methyl-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， 以 甲苯 、 正戊烷 为溶剂， 反应 16.83h， 生成 1-(2,2-二甲基环丙基)-1-庚醇
  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

文献信息

• Two new approaches to the 25-hydroxy-vitamin D2 side chain
  作者：Stephen R. Wilson、Andrew E. Davey、Maria E. Guazzaroni

  DOI：10.1021/jo00033a021

  日期：1992.3

  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.