2-(3-hydroxy-3-methyl-1-butynyl)adamantan-2-ol | 303015-49-8

• 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-methyl-1-butynyl)adamantan-2-ol
• 英文别名: 2-hydroxy-2-(3-hydroxy-3-methyl-1-butynyl)adamantane；2-(3-hydroxy-3-methylbut-1-ynyl)adamantan-2-ol；2-Hydroxy-2-(3-hydroxy-3-methyl-1-butynyl)-adamantane
• CAS: 303015-49-8
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: WOTQGYYVDISLEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 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-methyl-1-butynyl)adamantan-2-ol 在 镍 氢气 作用下， 以 乙醇 为溶剂， 以51%的产率得到2-(3-hydroxy-3-methylbutyl)adamantan-2-ol
  参考文献：
  名称：

  Zurabishvili; Lomidze; Samsonia, Sh.A., Russian Journal of Organic Chemistry, 2000, vol. 36, # 2, p. 218 - 221

  摘要：

  DOI：
• 作为产物：
  描述：

  金刚烷酮 在 乙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 13.0h， 生成 2-(3-hydroxy-3-methyl-1-butynyl)adamantan-2-ol
  参考文献：
  名称：

  Zurabishvili; Lomidze; Samsonia, Sh.A., Russian Journal of Organic Chemistry, 2000, vol. 36, # 2, p. 218 - 221

  摘要：

  DOI：

文献信息

• ——
  作者：V. I. Potkin、E. A. Dikusar、N. G. Kozlov

  DOI：10.1023/a:1021691426904

  日期：——

  A procedure has been proposed for the synthesis of tertiary acetylenic alcohols and diols by treatment of phenylacetylene or 2-methyl-3-butyn-2-ol with butyllithium and subsequent reaction of lithium phenylacetylide or lithium 4-lithio-2-methyl-3-butyn-2-olate thus obtained with alicyclic, aromatic, and terpene ketones.
• Transformations of 2-(3-Hydroxy-3-methyl-1-butynyl)adamantan-2-ol >Catalyzed by Acids
  作者：S. S. Koval'skaya、N. G. Kozlov、E. A. Dikusar

  DOI：10.1023/b:rujo.0000043712.63729.6e

  日期：2004.5

  Reaction of 2-(3-hydroxy-3-methyl-1-butynyl)adamantan-2-ol with acetonitrile under Ritter reaction conditions is accompanied by isomerization and partial hydration where the water addition to the triple bond occurs nonselectively. As a result of reaction carried out in the presence of 8 equiv of sulfuric acid a mixture was obtained of N-2-[4-(1-acetylaniino-2-adamantyl)-2-methyl-3-butyn-2-yl]acetamide, N-3-[1-(1-acetylamino-2-adarnantyl)-3-methyl-2-oxo-3-butyl]-acetamide, and N-3-[1-(1-acetylamino-2-adamantyl)-3-methyl-1-oxo-3)-butyl]acetamide in similar to10:3:2 ratio. In the presence of 2 equiv of the acid the mixture obtained consisted of N-2-[4-(1-acetylamino-2-adamantyl)-2-methyl-3-butyn-2-yl]acetamide, N-3-[1-(1-acetylamino-2-adamantyl)-3-methyl-2-oxo-3-butyl]acetamide, and 1-(acetylamino-2-adamantyl)-3-methyl-2-buten-1-one in the same ratio. In Rupe reaction conditions we obtained instead of the expected alpha, beta-unsaturated ketones a mixture of 1-(1-hydroxy-2-adamantyl)-3-hydroxy-3-methylbutan-1-one and 1-(1-hydroxy-2-adamantyl)-3-hydroxy-3-methylbutan-2-one in a 5:3 ratio.