(6R)-6-(3-methylbut-2-enyl)cyclohex-2-en-1-one | 868777-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R)-6-(3-methylbut-2-enyl)cyclohex-2-en-1-one
• CAS: 868777-92-8
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: UPYOTWCFEVGDHZ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (6R)-6-(3-methylbut-2-enyl)cyclohex-2-en-1-one 、 alkaline earth salt of/the/ methylsulfuric acid 以 乙醚 为溶剂， 反应 1.0h， 生成 (R)-1-Methyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enol
  参考文献：
  名称：

  Total Synthesis of (±)-Garsubellin A

  摘要：

  The first total synthesis of garsubellin A, a neurotrophic compound with potent choline acetyltransferase-inducing activity, is described. Keys for success were (1) stereoselective intermolecular aldol reaction at the C-4 position with acetaldehyde, (2) stereoelective Claisen rearrangement to introduce an allyl group to the most sterically crowded position at C-6, (3) ring-closing metathesis to construct the B-ring, and (4) Wacker-type oxidative C-ring formation. This synthetic route can be extended to an asymmetric synthesis of garsubellin A using the Koga catalytic enantioselective alkylation, which produced enantioenriched alpha-prenyl cyclohexenone with excellent enantioselectivity (95% ee).

  DOI：

  10.1021/ja055301t
• 作为产物：
  描述：

  1-(三甲基硅氧基)-3,4-二氢苯 、 1-溴-3-甲基-2-丁烯 生成 (6R)-6-(3-methylbut-2-enyl)cyclohex-2-en-1-one 、 (6S)-6-(3-methylbut-2-enyl)cyclohex-2-en-1-one
  参考文献：
  名称：

  Total Synthesis of (±)-Garsubellin A

  摘要：

  The first total synthesis of garsubellin A, a neurotrophic compound with potent choline acetyltransferase-inducing activity, is described. Keys for success were (1) stereoselective intermolecular aldol reaction at the C-4 position with acetaldehyde, (2) stereoelective Claisen rearrangement to introduce an allyl group to the most sterically crowded position at C-6, (3) ring-closing metathesis to construct the B-ring, and (4) Wacker-type oxidative C-ring formation. This synthetic route can be extended to an asymmetric synthesis of garsubellin A using the Koga catalytic enantioselective alkylation, which produced enantioenriched alpha-prenyl cyclohexenone with excellent enantioselectivity (95% ee).

  DOI：

  10.1021/ja055301t