2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol
• 英文别名: 2-(3-Hydroxy-3-methylbutyl)-1-(2-methylpropyl)cyclopropan-1-ol
• 化学式: C₁₂H₂₄O₂
• 分子量: 200.321
• InChiKey: OOLJKHJQYTVCFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以79%的产率得到8-hydroxy-2,5,8-trimethyl-4-nonanone
  参考文献：
  名称：

  Two-step synthesis of (±)-stigmolone, the pheromone of Stigmatella aurantiaca

  摘要：

  Racemic stigmolone (8-hydroxy-2,5,8-trimethyl-4-nonanone), the pheromone of myxobacterium Stigmatella aurantiaca, was synthesised in 67% overall yield, using titanium-mediated hydroxycyclopropanation of 2-methyl-5-hexen-2-ol with ethyl isovalerate followed by the base-induced ring opening of the resulting 2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00564-0
• 作为产物：
  描述：

  2-甲基-5-己烯-2-醇 、 异戊酸乙酯 在 titanium(IV) isopropylate 、 乙基溴化镁 作用下， 以 乙醚 为溶剂， 以85%的产率得到2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol
  参考文献：
  名称：

  Two-step synthesis of (±)-stigmolone, the pheromone of Stigmatella aurantiaca

  摘要：

  Racemic stigmolone (8-hydroxy-2,5,8-trimethyl-4-nonanone), the pheromone of myxobacterium Stigmatella aurantiaca, was synthesised in 67% overall yield, using titanium-mediated hydroxycyclopropanation of 2-methyl-5-hexen-2-ol with ethyl isovalerate followed by the base-induced ring opening of the resulting 2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)00564-0

文献信息

• Two-step synthesis of (±)-stigmolone, the pheromone of Stigmatella aurantiaca
  作者：Oleg L Epstein、Oleg G Kulinkovich

  DOI：10.1016/s0040-4039(01)00564-0

  日期：2001.5

  Racemic stigmolone (8-hydroxy-2,5,8-trimethyl-4-nonanone), the pheromone of myxobacterium Stigmatella aurantiaca, was synthesised in 67% overall yield, using titanium-mediated hydroxycyclopropanation of 2-methyl-5-hexen-2-ol with ethyl isovalerate followed by the base-induced ring opening of the resulting 2-(3-hydroxy-3-methylbutyl)-1-isobutyl-1-cyclopropanol. (C) 2001 Published by Elsevier Science Ltd.