trans,trans-3-pentyl-1,2-cyclohexanediol | 92210-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans,trans-3-pentyl-1,2-cyclohexanediol
• CAS: 92210-72-5
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: MGLPZHTVRQBYOB-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  n-pentyl lithium 在 六甲基磷酰三胺 、 sodium hydroxide 、 copper(l) iodide 、 dimethyl sulfide borane 、 双氧水 、 三乙胺 作用下， 反应 50.0h， 生成 trans,trans-3-pentyl-1,2-cyclohexanediol
  参考文献：
  名称：

  Saturated analogs of poison ivy allergens. Synthesis of trans,trans- and cis,trans-3-alkyl-1,2-cyclohexanediols and sensitizing properties in allergic contact dermatitis

  摘要：

  Saturated analogues of poison ivy and oak allergens (3-alkylcatechols), i.e. trans,trans-3-alkyl-1,2-cyclohexanediols (alkyl = CH3, n-C5H11, n-C10H21, n-C15H31), have been prepared and used to sensitize guinea pigs. Only long-chain derivatives (carbon chain length greater than C10) are contact sensitizers. The sensitized animals cross-react to PDC (i.e. pentadecylcatechol, one of the allergens of poison ivy), but the converse is not true (PDC-sensitized animals do not react to cyclohexanediols). cis,trans-3-n-Pentadecyl-1,2-cyclohexanediol has also been synthesized and shown to be a sensitizer. There is not cross-reaction between trans,trans- and cis,trans-3-n-pentadecylcyclohexanediols, excluding a common skin metabolite.

  DOI：

  10.1021/jm00152a018

文献信息

• Cyclohexane analogs of poison ivy and poison oak derivatives. A totally stereoselective synthesis of trans,trans-3-alkyl-1,2-cyclohexanediols.
  作者：Jean-Pierre Lepoittevin、Claude Benezra

  DOI：10.1016/s0040-4039(01)81216-8

  日期：1984.1