(1S,2S,4S)-8,8-Dimethyl-bicyclo[2.2.2]oct-5-en-2-ol | 52611-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,4S)-8,8-Dimethyl-bicyclo[2.2.2]oct-5-en-2-ol
• 英文别名: (1S,2S,4S)-8,8-dimethylbicyclo[2.2.2]oct-5-en-2-ol
• CAS: 52611-77-5
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: RKZAYEFYJPKCFM-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (1S,2S,4S)-8,8-Dimethyl-bicyclo[2.2.2]oct-5-en-2-ol 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (-)-(1S,4S)-8,8-dimethylbicyclo<2.2.2>oct-5-en-2-one
  参考文献：
  名称：

  Synthesis of Both Antipodal Forms of 7,7-Dimethylbicyclo[2.2.2]oct-2-en-5-one by Enantiomer Interconversion

  摘要：

  An enantioselective synthesis of both enantiomers of the title ketone 5 from a common achiral beta-diketone is reported. Bakers' yeast reduction of 6 cleanly differentiates between the two carbonyl groups to deliver (+)-9 in >90% yield, and with an ee exceeding 98%. Direct xanthate elimination leads to (+)-5. To arrive at the levorotatory antipode, the OH group in the beta-hydroxy ketone is transformed into the tetrahydropyranyl ether and the carbonyl group is subsequently reduced in advance of formal dehydration. Oxiadtion of the deprotected alcohol ultimately reestablishes the carbonyl functionality and delivers (-)-5 of equally high optical purity.

  DOI：

  10.1021/jo951552g
• 作为产物：
  描述：

  2-<<(1S,2S,4S)-8,8-dimethylbicyclo<2.2.2>oct-5-en-2-yl>oxy>tetrahydro-2H-pyran 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (1S,2S,4S)-8,8-Dimethyl-bicyclo[2.2.2]oct-5-en-2-ol
  参考文献：
  名称：

  Synthesis of Both Antipodal Forms of 7,7-Dimethylbicyclo[2.2.2]oct-2-en-5-one by Enantiomer Interconversion

  摘要：

  An enantioselective synthesis of both enantiomers of the title ketone 5 from a common achiral beta-diketone is reported. Bakers' yeast reduction of 6 cleanly differentiates between the two carbonyl groups to deliver (+)-9 in >90% yield, and with an ee exceeding 98%. Direct xanthate elimination leads to (+)-5. To arrive at the levorotatory antipode, the OH group in the beta-hydroxy ketone is transformed into the tetrahydropyranyl ether and the carbonyl group is subsequently reduced in advance of formal dehydration. Oxiadtion of the deprotected alcohol ultimately reestablishes the carbonyl functionality and delivers (-)-5 of equally high optical purity.

  DOI：

  10.1021/jo951552g

文献信息

• Synthesis of Both Antipodal Forms of 7,7-Dimethylbicyclo[2.2.2]oct-2-en-5-one by Enantiomer Interconversion
  作者：Leo A. Paquette、Hon-Chung Tsui

  DOI：10.1021/jo951552g

  日期：1996.1.1

  An enantioselective synthesis of both enantiomers of the title ketone 5 from a common achiral beta-diketone is reported. Bakers' yeast reduction of 6 cleanly differentiates between the two carbonyl groups to deliver (+)-9 in >90% yield, and with an ee exceeding 98%. Direct xanthate elimination leads to (+)-5. To arrive at the levorotatory antipode, the OH group in the beta-hydroxy ketone is transformed into the tetrahydropyranyl ether and the carbonyl group is subsequently reduced in advance of formal dehydration. Oxiadtion of the deprotected alcohol ultimately reestablishes the carbonyl functionality and delivers (-)-5 of equally high optical purity.