(+/)-2-Methyloctadec-7-yn-6-ol | 157488-28-3

• 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: (+/)-2-Methyloctadec-7-yn-6-ol
• 英文别名: 2-Methyloctadec-7-yn-6-ol
• CAS: 157488-28-3
• 化学式: C₁₉H₃₆O
• 分子量: 280.494
• InChiKey: HSQCFTNPHIPOGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (+/)-2-Methyloctadec-7-yn-6-ol 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以68%的产率得到2-Methyloctadec-7-yn-6-one
  参考文献：
  名称：

  Synthesis and Inhibitory Properties of Pheromone Analogs for the Epoxide Hydrolase of the Gypsy Moth

  摘要：

  A series of analogues of disparlure, the gypsy moth (Lymantria dispar) sex attractant, was synthesized, and the potency of these inhibitors in suppressing the metabolism of disparlure by the L. dispar epoxide hydrolase (EH) was determined. The analogues substituted at the 6-position (6-hydroxy-, 6-oxo-, and 6,6-difluorodisparlure; (+/-)-threo,cis-11, (+/-)-13, and (+/-)-17, respectively), along with 9,9-difluorodisparlure [(+/-)-26], were the most potent inhibitors (IC50 values of 4-9 mu M). Two other 9-substituted analogues, 9-hydroxydisparlure [(+/-)-threo,cis-21] and 9-oxodisparlure [(+/-)-22], were slightly less potent (IC50 values of 18 and 30 mu M, respectively). Analogues substituted at both the 6- and 9-positions (threo,erythro-6,9-dihydroxy-, threo,threo-6,9-dihydroxy-, and 6,9-dioxodisparlure; (+/-)-threo,erythro-32, (+/-)-threo,threo-32, and (+/-)-33, respectively) were generally the least potent inhibitors (IC50 values of 27-200 mu M). On the basis of a model of the EH active site, a hypothesis is advanced to rationalize the higher potencies of the 6-substituted analogues. Pheromone metabolism plays a key role in pheromone perception, and the potential consequences of inhibition of pheromone metabolism are discussed.

  DOI：

  10.1021/jo00090a012
• 作为产物：
  描述：

  5-甲基-1-己醇 在 重铬酸吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 22.42h， 生成 (+/)-2-Methyloctadec-7-yn-6-ol
  参考文献：
  名称：

  Synthesis and Inhibitory Properties of Pheromone Analogs for the Epoxide Hydrolase of the Gypsy Moth

  摘要：

  A series of analogues of disparlure, the gypsy moth (Lymantria dispar) sex attractant, was synthesized, and the potency of these inhibitors in suppressing the metabolism of disparlure by the L. dispar epoxide hydrolase (EH) was determined. The analogues substituted at the 6-position (6-hydroxy-, 6-oxo-, and 6,6-difluorodisparlure; (+/-)-threo,cis-11, (+/-)-13, and (+/-)-17, respectively), along with 9,9-difluorodisparlure [(+/-)-26], were the most potent inhibitors (IC50 values of 4-9 mu M). Two other 9-substituted analogues, 9-hydroxydisparlure [(+/-)-threo,cis-21] and 9-oxodisparlure [(+/-)-22], were slightly less potent (IC50 values of 18 and 30 mu M, respectively). Analogues substituted at both the 6- and 9-positions (threo,erythro-6,9-dihydroxy-, threo,threo-6,9-dihydroxy-, and 6,9-dioxodisparlure; (+/-)-threo,erythro-32, (+/-)-threo,threo-32, and (+/-)-33, respectively) were generally the least potent inhibitors (IC50 values of 27-200 mu M). On the basis of a model of the EH active site, a hypothesis is advanced to rationalize the higher potencies of the 6-substituted analogues. Pheromone metabolism plays a key role in pheromone perception, and the potential consequences of inhibition of pheromone metabolism are discussed.

  DOI：

  10.1021/jo00090a012

文献信息

• Synthesis and Inhibitory Properties of Pheromone Analogs for the Epoxide Hydrolase of the Gypsy Moth
  作者：Steven M. Graham、Glenn D. Prestwich

  DOI：10.1021/jo00090a012

  日期：1994.6

  A series of analogues of disparlure, the gypsy moth (Lymantria dispar) sex attractant, was synthesized, and the potency of these inhibitors in suppressing the metabolism of disparlure by the L. dispar epoxide hydrolase (EH) was determined. The analogues substituted at the 6-position (6-hydroxy-, 6-oxo-, and 6,6-difluorodisparlure; (+/-)-threo,cis-11, (+/-)-13, and (+/-)-17, respectively), along with 9,9-difluorodisparlure [(+/-)-26], were the most potent inhibitors (IC50 values of 4-9 mu M). Two other 9-substituted analogues, 9-hydroxydisparlure [(+/-)-threo,cis-21] and 9-oxodisparlure [(+/-)-22], were slightly less potent (IC50 values of 18 and 30 mu M, respectively). Analogues substituted at both the 6- and 9-positions (threo,erythro-6,9-dihydroxy-, threo,threo-6,9-dihydroxy-, and 6,9-dioxodisparlure; (+/-)-threo,erythro-32, (+/-)-threo,threo-32, and (+/-)-33, respectively) were generally the least potent inhibitors (IC50 values of 27-200 mu M). On the basis of a model of the EH active site, a hypothesis is advanced to rationalize the higher potencies of the 6-substituted analogues. Pheromone metabolism plays a key role in pheromone perception, and the potential consequences of inhibition of pheromone metabolism are discussed.