2-(2-cyclohexenyl)-2-methyl-3-buten-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-cyclohexenyl)-2-methyl-3-buten-1-ol
• 英文别名: 2-Cyclohex-2-en-1-yl-2-methylbut-3-en-1-ol
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: LFXYNDZZXABLQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  一氧化异戊二烯 、 (2-cyclohexenyl)dicyclohexylborane 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 76.0h， 生成 2-(2-cyclohexenyl)-2-methyl-3-buten-1-ol 、 (Z)-4-cyclohex-2-en-1-yl-2-methylbut-2-en-1-ol 、 (E)-4-cyclohex-2-en-1-yl-2-methylbut-2-en-1-ol
  参考文献：
  名称：

  Syntheses with Organoboranes. XI. Allylboration of Vinylic Epoxides with Allylic Dialkylboranes

  摘要：

  Allylboration of representative vinylic epoxides with allyldiethylborane (1) and (2-cyclahexenyl)dicyclohexyl borane (2) affords the corresponding 1,2- and 1,4-addition products. cis-1,2-Addition is favored in the reaction of 1 with 3,4-epoxycycloalkenes of six- to eight-membered rings. 3,4-Epoxycyclopentene (3a) and 5,5-dimethyl-3,4-epoxycyclopentene (3b) undergo five-membered ring opening during allylboration with 1 and 2, producing the corresponding (Z)-trienols (4a and 4b) with high stereoselectivity. 1,4-Addition of 1 and 2 to monoepoxides of 1,3-butadiene and isoprene is favored, producing predominantly the corresponding (E)-alcohols.

  DOI：

  10.1021/ol006641g

文献信息

• Syntheses with Organoboranes. XI. Allylboration of Vinylic Epoxides with Allylic Dialkylboranes
  作者：Marek Zaidlewicz、Marek P. Krzemiński

  DOI：10.1021/ol006641g

  日期：2000.11.1

  Allylboration of representative vinylic epoxides with allyldiethylborane (1) and (2-cyclahexenyl)dicyclohexyl borane (2) affords the corresponding 1,2- and 1,4-addition products. cis-1,2-Addition is favored in the reaction of 1 with 3,4-epoxycycloalkenes of six- to eight-membered rings. 3,4-Epoxycyclopentene (3a) and 5,5-dimethyl-3,4-epoxycyclopentene (3b) undergo five-membered ring opening during allylboration with 1 and 2, producing the corresponding (Z)-trienols (4a and 4b) with high stereoselectivity. 1,4-Addition of 1 and 2 to monoepoxides of 1,3-butadiene and isoprene is favored, producing predominantly the corresponding (E)-alcohols.