(1R,2R,4S)-2-(bromomethyl)-2-methyl-3-methylidenebicyclo[2.2.1]heptane | 129704-45-6

• 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: (1R,2R,4S)-2-(bromomethyl)-2-methyl-3-methylidenebicyclo[2.2.1]heptane
• CAS: 129704-45-6
• 化学式: C₁₀H₁₅Br
• 分子量: 215.133
• InChiKey: BKYNWRMRJLEMSI-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  白樟油 在 氯磺酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢溴酸 、 溴 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (1R,2R,4S)-2-(bromomethyl)-2-methyl-3-methylidenebicyclo[2.2.1]heptane
  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

文献信息

• Synthesis and absolute configuration of the antiparasitic furanosesquiterpenes (-)-furodysin and (-)-furodysinin. Camphor as a six-membered ring chiral pool template
  作者：Valerie Vaillancourt、Mohamad R. Agharahimi、Uma N. Sundram、Olivier Richou、D. John Faulkner、Kim F. Albizati

  DOI：10.1021/jo00001a069

  日期：1991.1

  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.