2-(dibromomethyl)-8,9-didehydroadamantan-2-ol | 138899-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(dibromomethyl)-8,9-didehydroadamantan-2-ol
• 英文别名: 5-(Dibromomethyl)tetracyclo[4.3.1.02,4.03,8]decan-5-ol
• CAS: 138899-11-3
• 化学式: C₁₁H₁₄Br₂O
• 分子量: 322.04
• InChiKey: HNFZAZNCWLKKSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(dibromomethyl)-8,9-didehydroadamantan-2-ol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以67%的产率得到2,11-dehydro-5-homoadamantanone
  参考文献：
  名称：

  Ring expansions of simple cyclic conjugated cyclopropyl ketones by the Nozaki method are not regiospecific

  摘要：

  DOI：

  10.1021/jo00032a058
• 作为产物：
  描述：

  8,9-Dehydro-2-adamantanon 、 二溴甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 1.0h， 以81%的产率得到2-(dibromomethyl)-8,9-didehydroadamantan-2-ol
  参考文献：
  名称：

  On the reaction of (dibromomethyl)lithium with bicyclic and tricyclic ketones

  摘要：

  Many literature examples show that the reaction of a simple cyclic ketone with (dibromomethyl)-lithium at -78-degrees-C followed by low-temperature hydrolysis of the resulting lithium alkoxide 33, gives the corresponding dibromomethyl alcohol. We have found that the reaction of a bicyclic or tricyclic ketone with (dibromomethyl)lithium under comparable conditions provides a dibromomethyl alcohol and/or an alpha-bromo aldehyde. The latter product appears to result from an intramolecular displacement reaction in 33 to give a bromo epoxide, which then rearranges stereospecifically to the alpha-bromo aldehyde. The product ratios obtained in all of these reactions seem to be determined by the steric interactions in 33 between the alkoxide and dibromomethyl groups and the hydrogens that are syn to them at the carbons which are beta to the original carbonyl carbon. As these steric interactions increase, the proportion of alpha-bromo aldehyde in the product mixture increases. If 33 obtained from any cyclic ketone is warmed to 10-degrees-C before it is hydrolyzed, then the only product isolated is the alpha-bromo aldehyde

  DOI：

  10.1021/jo00072a037