endo-9-bromobornan-2-ol mesylate | 129594-61-2

• 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
• 英文名称: endo-9-bromobornan-2-ol mesylate
• CAS: 129594-61-2
• 化学式: C₁₁H₁₉BrO₃S
• 分子量: 311.24
• InChiKey: BTOHQAHCYSOEQZ-RCWTZXSCSA-N

物化性质

• 沸点：
  390.6±11.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  endo-9-bromobornan-2-ol mesylate 在 sodium naphthaleimide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 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-溴樟脑 在 氯磺酸 、 4-二甲氨基吡啶 、 溴 、 aluminum isopropoxide 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 103.0h， 生成 endo-9-bromobornan-2-ol mesylate
  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