1-(3-bromoadamantan-1-yl)propan-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-bromoadamantan-1-yl)propan-2-one
• 英文别名: 1-(1-Brom-1-adamantyl)-2-propanon；1-(3-Bromo-adamantan-1-yl)-propan-2-one；1-(3-bromo-1-adamantyl)propan-2-one
• 化学式: C₁₃H₁₉BrO
• 分子量: 271.197
• InChiKey: GWDZCKKSXFQQAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-bromoadamantan-1-yl)propan-2-one 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 硫酸 、 水 、 二硫代碳酸-O-丁酯钠盐 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 16.0h， 生成 3-(3-hydroxyadamantan-1-yl)propanoic acid
  参考文献：
  名称：

  Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives

  摘要：

  The Willgerodt-Kindler reaction of 1-(1-adamantyl)propan-2-one and its derivatives was studied by gas chromatography-mass spectrometry. The reaction time was found to be 3-4 times longer than in the case of alkyl aryl ketones due to considerable steric hindrances in the molecules of adamantyl ketones. The use of diglyme as solvent and sodium butyl xanthate as catalyst significantly shortened the reaction time and improved the yield to 92%.

  DOI：

  10.1134/s1070363217120027
• 作为产物：
  描述：

  乙酸异丙烯酯 、 1,3-二溴金刚烷 在 aluminum tri-bromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以76%的产率得到1-(3-bromoadamantan-1-yl)propan-2-one
  参考文献：
  名称：

  Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives

  摘要：

  The Willgerodt-Kindler reaction of 1-(1-adamantyl)propan-2-one and its derivatives was studied by gas chromatography-mass spectrometry. The reaction time was found to be 3-4 times longer than in the case of alkyl aryl ketones due to considerable steric hindrances in the molecules of adamantyl ketones. The use of diglyme as solvent and sodium butyl xanthate as catalyst significantly shortened the reaction time and improved the yield to 92%.

  DOI：

  10.1134/s1070363217120027

文献信息

• Chemistry of adamantane. VII. Adamantanealkanamines as potential antidepressant and anti-Parkinson agents
  作者：Jiban K. Chakrabarti、Michael J. Foulis、Terrence M. Hotten、Stephen S. Szinai、Alec Todd

  DOI：10.1021/jm00252a007

  日期：1974.6
• Peculiar Features of the Willgerodt–Kindler Reaction of 1-Adamantylpropan-2-one and Its Derivatives
  作者：I. A. Novakov、B. S. Orlinson、E. N. Savel’ev、E. A. Potaenkova、O. V. Vostrikova、D. P. Tarakanov、M. A. Nakhod

  DOI：10.1134/s1070363217120027

  日期：2017.12

  The Willgerodt-Kindler reaction of 1-(1-adamantyl)propan-2-one and its derivatives was studied by gas chromatography-mass spectrometry. The reaction time was found to be 3-4 times longer than in the case of alkyl aryl ketones due to considerable steric hindrances in the molecules of adamantyl ketones. The use of diglyme as solvent and sodium butyl xanthate as catalyst significantly shortened the reaction time and improved the yield to 92%.