(1R,3R,4R)-3-[(1R)-1-hydroxy-2-methylpropyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one | 129594-71-4

• 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,3R,4R)-3-[(1R)-1-hydroxy-2-methylpropyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
• CAS: 129594-71-4
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: FENYLFFNLYQXAU-BIAAXOCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,4R)-3-[(1S)-1-hydroxy-2-methylpropyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 、 (1R,3R,4R)-3-[(1R)-1-hydroxy-2-methylpropyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 、 乙酸酐 、 三乙胺 生成 [(1S)-2-methyl-1-[(1R,2S,4R)-4,7,7-trimethyl-3-oxo-2-bicyclo[2.2.1]heptanyl]propyl] acetate
  参考文献：
  名称：

  HUTCHINSON, J. H.;LI, D. L. F.;MONEY, T.;PALME, M.;AGHARAHIMI, M. R.;ALBI+, CAN. J. CHEM., 69,(1991) N, C. 558-566

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,3S,4R)-3-[(R)-hydroxy(phenyl)methyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.75h， 生成 (1R,3R,4R)-3-[(1R)-1-hydroxy-2-methylpropyl]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  Hutchinson, J. H.; Li, D. L. F.; Money, T., Canadian Journal of Chemistry, 1991, vol. 69, # 3, p. 558 - 566

  摘要：

  DOI：

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.