methyl 2-[(4aR,5S,7R,8aS)-1-benzyl-7-methyl-4a-(4-oxobutanoyl)-2,3,4,5,6,7,8,8a-octahydroquinolin-5-yl]acetate | 1390644-55-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: methyl 2-[(4aR,5S,7R,8aS)-1-benzyl-7-methyl-4a-(4-oxobutanoyl)-2,3,4,5,6,7,8,8a-octahydroquinolin-5-yl]acetate
• CAS: 1390644-55-9
• 化学式: C₂₄H₃₃NO₄
• 分子量: 399.53
• InChiKey: GBCXMJAJNMTPNE-KDNSLJGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-[(4aR,5S,7R,8aS)-1-benzyl-7-methyl-4a-(4-oxobutanoyl)-2,3,4,5,6,7,8,8a-octahydroquinolin-5-yl]acetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， -78.0~110.0 ℃ 、354.66 kPa 条件下， 反应 5.25h， 生成 (1S,2S,4R,6S,9S)-4-methyl-13-azatetracyclo[7.7.0.01,6.02,13]hexadecan-8-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
• 作为产物：
  描述：

  methyl 2-[(1S,5R)-5-methyl-3-oxo-2-pent-4-enoylcyclohexyl]acetate 在 sodium triacetylborohydride 、 H₄O₆Os^(2-)*K⁽¹⁺⁾ 、 溶剂黄146 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 1,1-二氯乙烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 15.0h， 生成 methyl 2-[(4aR,5S,7R,8aS)-1-benzyl-7-methyl-4a-(4-oxobutanoyl)-2,3,4,5,6,7,8,8a-octahydroquinolin-5-yl]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

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.