1,3,6-Tribromadamantan | 28558-18-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1,3,6-Tribromadamantan
• 英文别名: 1,3,6-Tribromoadamantane
• CAS: 28558-18-1
• 化学式: C₁₀H₁₃Br₃
• 分子量: 372.925
• InChiKey: SRCGCORNXOCEHL-UHFFFAOYSA-N

物化性质

• 沸点：
  337.2±32.0 °C(Predicted)
• 密度：
  2.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,3,6-Tribromadamantan 在 四氯化锡 作用下， 以 苯 为溶剂， 生成 2,5-Dibromo-7-chloroadamantane
  参考文献：
  名称：

  Face selection in the reduction of p,p'-disubstituted 5,7-diphenyl-2-adamantanones and hydrolysis of the corresponding 2-adamantyl tosylates

  摘要：

  The reduction of 5,7-diphenyl-2-adamantanone with sodium borohydride in 2-propanol is affected by the introduction of a p-nitro substituent in one of the rings: the E-alcohol is obtained in small but easily measurable excess of 1.30:1. Conversely, the introduction of a p-amino group leads to an excess of Z-isomer by roughly the same factor (1.28). When both substituents are present, they evidently cooperate to produce a ratio of 1.64. The tosylates of the alcohols were prepared and their solvolysis rates measured in 3% aqueous hexafluoro-2-propanol and compared with those of the parent and p-substituted 5-phenyl-2-adamantyl tosylates. Additivity of substituent effects was again observed, but the p-aminophenyl group in these reactions was deactivating compared to phenyl, presumably due to II-bonding and/or protonation of the amino group in the acidic medium.

  DOI：

  10.1021/jo00080a012
• 作为产物：
  描述：

  金刚烷酮 在 二溴亚砜 、 溴 、 铁粉 作用下， 反应 24.0h， 生成 1,3,6-Tribromadamantan
  参考文献：
  名称：

  5,6-二溴金刚烷-2-一和-2-醇的半品醇和原金刚烷-金刚烷重排

  摘要：

  在Friedel-Crafts条件下，通过2,2,6,6-四溴金刚烷的重排和溴化反应，形成了许多新的多溴化金刚烷。原金刚烷-4,10-二酮，10-乙酰氧基原金刚烷-4-一，1,2,6-三乙酰氧基金刚烷和5,6-二乙酰氧基金刚烷-2-一是通过连续的5,6-二金刚烷- 2-一和5，6-二溴金刚烷-2-醇。这项工作可能为合成1,2,6-三取代的金刚烷打开新的途径。

  DOI：

  10.1016/j.tet.2017.04.006

文献信息

• US4990691A
  申请人：——

  公开号：US4990691A

  公开（公告）日：1991-02-05
• Semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and -2-ol
  作者：Xiaofang Wang、Yuxiang Dong、Edward L. Ezell、Jered C. Garrison、James K. Wood、James P. Hagen、Jonathan L. Vennerstrom

  DOI：10.1016/j.tet.2017.04.006

  日期：2017.5

  A number of new polybrominated adamantanes were formed by rearrangements and bromination of 2,2,6,6-tetrabromoadamantane under Friedel-Crafts conditions. Protoadamantane-4,10-dione, 10-acetoxyprotoadamantan-4-one, 1,2,6-triacetoxyadamantane and 5,6-diacetoxyadamantan-2-one were formed by successive semipinacol and protoadamantane-adamantane rearrangements of 5,6-dibromoadamantan-2-one and 5,6-dibromoadamantan-2-ol

  在Friedel-Crafts条件下，通过2,2,6,6-四溴金刚烷的重排和溴化反应，形成了许多新的多溴化金刚烷。原金刚烷-4,10-二酮，10-乙酰氧基原金刚烷-4-一，1,2,6-三乙酰氧基金刚烷和5,6-二乙酰氧基金刚烷-2-一是通过连续的5,6-二金刚烷- 2-一和5，6-二溴金刚烷-2-醇。这项工作可能为合成1,2,6-三取代的金刚烷打开新的途径。
• Face selection in the reduction of p,p'-disubstituted 5,7-diphenyl-2-adamantanones and hydrolysis of the corresponding 2-adamantyl tosylates
  作者：In H. Song、William J. le Noble

  DOI：10.1021/jo00080a012

  日期：1994.1

  The reduction of 5,7-diphenyl-2-adamantanone with sodium borohydride in 2-propanol is affected by the introduction of a p-nitro substituent in one of the rings: the E-alcohol is obtained in small but easily measurable excess of 1.30:1. Conversely, the introduction of a p-amino group leads to an excess of Z-isomer by roughly the same factor (1.28). When both substituents are present, they evidently cooperate to produce a ratio of 1.64. The tosylates of the alcohols were prepared and their solvolysis rates measured in 3% aqueous hexafluoro-2-propanol and compared with those of the parent and p-substituted 5-phenyl-2-adamantyl tosylates. Additivity of substituent effects was again observed, but the p-aminophenyl group in these reactions was deactivating compared to phenyl, presumably due to II-bonding and/or protonation of the amino group in the acidic medium.