(+)-内-3,9-二溴樟脑 | 85719-15-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (+)-内-3,9-二溴樟脑
• 英文名称: (+)-endo-3,9-dibromocamphor
• 英文别名: endo-3,9-dibromocamphor；(+)-3,8-dibromocamphor；(1R,3S,4S,7S)-3-bromo-7-(bromomethyl)-1,7-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 85719-15-9
• 化学式: C₁₀H₁₄Br₂O
• 分子量: 310.029
• InChiKey: DCDNKSJBRIJYEC-KKHAAJSZSA-N

物化性质

• 沸点：
  314.5±17.0 °C(Predicted)
• 密度：
  1.689±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (+)-内-3,9-二溴樟脑 在 sodium naphthaleimide 、 氨 、 lithium 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 (+)-对-薄荷-1-烯
  参考文献：
  名称：

  Synthesis and absolute configuration of the antiparasitic furanosesquiterpenes (-)-furodysin and (-)-furodysinin. Camphor as a six-membered ring chiral pool template

  摘要：

  The syntheses of (-)-furodysin ((-)-2a) and (-)-furodysinin ((-)-3a) in four steps starting from (+)-9-bromocamphor (18) has been accomplished, thus establishing the absolute configuration of these and related metabolites. This was made possible by the unexpected exo selectivity in the aldol condensation of camphor-like enolates with aldehydes. This has been found to be a general phenomenon in the camphor system. Further, anionic fragmentation of the C1-C7 bond of camphor derivatives has allowed access to synthetic intermediates containing functionalized six-membered rings, thus opening up avenues from camphor to a new class of chiral pool elements not currently available from chiral pool substances.

  DOI：

  10.1021/jo00001a069
• 作为产物：
  描述：

  3,3-二溴-1,7,7-三甲基双环[2.2.1]庚烷-2-酮 在 氯磺酸 、 溴 、 溶剂黄146 作用下， 反应 32.0h， 生成 (+)-内-3,9-二溴樟脑
  参考文献：
  名称：

  Dadson, William M.; Lam, Mayda; Money, Thomas, Canadian Journal of Chemistry, 1983, vol. 61, p. 343 - 346

  摘要：

  DOI：

文献信息

• The stereochemical requirement in the fragmentation of 9-bromocamphor derivatives. A new class of chiral pool elements containing asymmetric quaternary carbon centers
  作者：Uma N. Sundram、Kim F. Albizati

  DOI：10.1021/jo00008a010

  日期：1991.4

  The fragmentation of 9-bromobornan-2-ol derivatives is dependent on both the orientation and identity of the leaving group at the 2-position. This has led to a synthesis of compounds containing useful quaternary carbon centers in carbocyclic six-membered rings, a previously unknown type of chiral pool elements.