(1R,2S,4aR,8aR)-2,4a-Dimethyl-5-methylene-decahydro-naphthalen-1-ol | 137789-16-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,4aR,8aR)-2,4a-Dimethyl-5-methylene-decahydro-naphthalen-1-ol
• 英文别名: (1R,2S,4aR,8aR)-2,4a-dimethyl-5-methylidene-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-ol
• CAS: 137789-16-3
• 化学式: C₁₃H₂₂O
• 分子量: 194.317
• InChiKey: VTDZPIGCUSWGRA-SYEHKZFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (1R,2S,4aR,8aR)-2,4a-Dimethyl-5-methylene-decahydro-naphthalen-1-ol 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(4aR)-2,4a-dimethyl-5-methylene-trans-octahydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Use of the Me3Sn function as a readily removable ‘anchoring’ group in the synthesis of enantiomerically pure bicyclic alcohols and ketones

  摘要：

  Subjection of (5R, 6R)-(-)-3,6-dimethyl-5-trimethylstannyl-2-cyclohexen-1-one (11) to appropriate annulation sequences provides the cis-fused ketones 15, 20, and 21, which, upon reduction (Li, NH3, THF,t-BuOH) are converted smoothly into the enantiomerically pure bicyclic alcohols 16, 22, and 23, respectively. Compound 16 is readily transformed into the unichiral ketones 6 and 7.

  DOI：

  10.1016/s0040-4039(00)92348-7
• 作为产物：
  描述：

  (R)-5-methyl-cyclohex-2-enone 、 lithium,5-chloropent-1-ene 、 碘甲烷 生成 (1R,2S,4aR,8aR)-2,4a-Dimethyl-5-methylene-decahydro-naphthalen-1-ol
  参考文献：
  名称：

  Use of the Me3Sn function as a readily removable ‘anchoring’ group in the synthesis of enantiomerically pure bicyclic alcohols and ketones

  摘要：

  Subjection of (5R, 6R)-(-)-3,6-dimethyl-5-trimethylstannyl-2-cyclohexen-1-one (11) to appropriate annulation sequences provides the cis-fused ketones 15, 20, and 21, which, upon reduction (Li, NH3, THF,t-BuOH) are converted smoothly into the enantiomerically pure bicyclic alcohols 16, 22, and 23, respectively. Compound 16 is readily transformed into the unichiral ketones 6 and 7.

  DOI：

  10.1016/s0040-4039(00)92348-7

文献信息

• Use of the Me3Sn function as a readily removable ‘anchoring’ group in the synthesis of enantiomerically pure bicyclic alcohols and ketones
  作者：Edward Piers、Jacques Y. Roberge

  DOI：10.1016/s0040-4039(00)92348-7

  日期：1991.9

  Subjection of (5R, 6R)-(-)-3,6-dimethyl-5-trimethylstannyl-2-cyclohexen-1-one (11) to appropriate annulation sequences provides the cis-fused ketones 15, 20, and 21, which, upon reduction (Li, NH3, THF,t-BuOH) are converted smoothly into the enantiomerically pure bicyclic alcohols 16, 22, and 23, respectively. Compound 16 is readily transformed into the unichiral ketones 6 and 7.