1-bromomethyldiamantane | 1551616-57-9

• 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-bromomethyldiamantane
• 英文别名: 1-Bromomethyldiamantane；1-(bromomethyl)pentacyclo[7.3.1.14,12.02,7.06,11]tetradecane
• CAS: 1551616-57-9
• 化学式: C₁₅H₂₁Br
• 分子量: 281.236
• InChiKey: VUHGATIERUTOOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  7.0
• 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

• 作为产物：
  描述：

  N-甲基-N-亚硝基对甲苯磺酰胺 在 溴 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 15.25h， 生成 1-bromomethyldiamantane
  参考文献：
  名称：

  Functionalization of Homodiamantane: Oxygen Insertion Reactions without Rearrangement with Dimethyldioxirane

  摘要：

  Homodiamantane bromination and nitroxylation are accompanied by contraction of the seven-membered ring to give the corresponding substituted 1-diamantylmethyl derivatives. In contrast, CH-bond hydroxylations with dimethyldioxirane retain the cage and give both apically and medially substituted homodiamantanes. The product ratios are in accord with the barriers for the oxygen insertion computed with density functional theory methods only if solvation is included through a polarizable continuum model. B3LYP-D3 and M06-2X computations with a 6-31G(d,p) basis set on the oligomeric van der Waals complexes predict the potential of homodiamantane derivatives for surface modifications with conformationally slightly flexible diamondoid homologues.

  DOI：

  10.1021/jo4026594

文献信息

• Functionalization of Homodiamantane: Oxygen Insertion Reactions without Rearrangement with Dimethyldioxirane
  作者：Andrey A. Fokin、Tatyana S. Zhuk、Alexander E. Pashenko、Valeriy V. Osipov、Pavel A. Gunchenko、Michael Serafin、Peter R. Schreiner

  DOI：10.1021/jo4026594

  日期：2014.2.21

  Homodiamantane bromination and nitroxylation are accompanied by contraction of the seven-membered ring to give the corresponding substituted 1-diamantylmethyl derivatives. In contrast, CH-bond hydroxylations with dimethyldioxirane retain the cage and give both apically and medially substituted homodiamantanes. The product ratios are in accord with the barriers for the oxygen insertion computed with density functional theory methods only if solvation is included through a polarizable continuum model. B3LYP-D3 and M06-2X computations with a 6-31G(d,p) basis set on the oligomeric van der Waals complexes predict the potential of homodiamantane derivatives for surface modifications with conformationally slightly flexible diamondoid homologues.