(5R)-5-methyl-2-pent-4-enoylcyclohex-2-en-1-one | 1390644-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R)-5-methyl-2-pent-4-enoylcyclohex-2-en-1-one
• CAS: 1390644-48-0
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: QCFVOESXROLJIH-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R)-5-methyl-2-pent-4-enoylcyclohex-2-en-1-one 在 lithium perchlorate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 methyl 2-[(1S,2S,5R)-5-methyl-3-oxo-2-(3-oxopropyl)-2-pent-4-enoylcyclohexyl]acetate
  参考文献：
  名称：

  Protecting Group-Free Total Synthesis of (−)-Lannotinidine B

  摘要：

  The first total synthesis of (-)-lannotinidine B, a unique tetracyclic constitutent of Lycopodium annotinum, has been accomplished in 10 steps with 23% overall yield. The completed short and efficient synthesis is characterized with three highly chemo- and/or stereoselective reductive-amination steps to furnish the desired trans-fused 6/6 bicycle and the aza seven-membered ring system, and a direct intramolecular acyloin condensation to deliver the cyclopentanone moiety, as well as successful application of a protecting group-free strategy and an optimal redox order.

  DOI：

  10.1021/ja305261h
• 作为产物：
  描述：

  (R)-5-methyl-cyclohex-2-enone 在 三丁基膦 、 1,1'-binaphthyl-8,8'-diol 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 98.0h， 生成 (5R)-5-methyl-2-pent-4-enoylcyclohex-2-en-1-one
  参考文献：
  名称：

  Protecting Group-Free Total Synthesis of (−)-Lannotinidine B

  摘要：

  The first total synthesis of (-)-lannotinidine B, a unique tetracyclic constitutent of Lycopodium annotinum, has been accomplished in 10 steps with 23% overall yield. The completed short and efficient synthesis is characterized with three highly chemo- and/or stereoselective reductive-amination steps to furnish the desired trans-fused 6/6 bicycle and the aza seven-membered ring system, and a direct intramolecular acyloin condensation to deliver the cyclopentanone moiety, as well as successful application of a protecting group-free strategy and an optimal redox order.

  DOI：

  10.1021/ja305261h

文献信息

• Protecting Group-Free Total Synthesis of (−)-Lannotinidine B
  作者：Hui Ming Ge、Lan-De Zhang、Ren Xiang Tan、Zhu-Jun Yao

  DOI：10.1021/ja305261h

  日期：2012.8.1

  The first total synthesis of (-)-lannotinidine B, a unique tetracyclic constitutent of Lycopodium annotinum, has been accomplished in 10 steps with 23% overall yield. The completed short and efficient synthesis is characterized with three highly chemo- and/or stereoselective reductive-amination steps to furnish the desired trans-fused 6/6 bicycle and the aza seven-membered ring system, and a direct intramolecular acyloin condensation to deliver the cyclopentanone moiety, as well as successful application of a protecting group-free strategy and an optimal redox order.