1,7-bis((7R,8aR)-1-ethanoyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl)heptane-2,6-dione | 1202395-00-3

• 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: 1,7-bis((7R,8aR)-1-ethanoyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl)heptane-2,6-dione
• 英文别名: 1,7-bis[(7R,8aR)-1-acetyl-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-5-yl]heptane-2,6-dione
• CAS: 1202395-00-3
• 化学式: C₃₁H₄₆N₂O₄
• 分子量: 510.717
• InChiKey: PVWCHRZMIJYUET-MLMKKTDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,7-bis((7R,8aR)-1-ethanoyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl)heptane-2,6-dione 在 三氟乙酸铵 、 三乙酰氧基硼氢化钠 、 sodium methoxide-d3 作用下， 以 四氢呋喃 、 氘代甲醇 为溶剂， 反应 144.0h， 以29%的产率得到lycoperine A
  参考文献：
  名称：

  Total Synthesis of (−)-Lycoperine A

  摘要：

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.

  DOI：

  10.1021/ol902389e
• 作为产物：
  描述：

  (2R,6S)-2,6-bis[[(7R,8aR)-1-acetyl-7-methyl-3,4,6,7,8,8a-hexahydro-2H-quinolin-5-yl]methyl]-1-benzylpiperidine-2,6-dicarbonitrile 在 silver nitrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 以84%的产率得到1,7-bis((7R,8aR)-1-ethanoyl-7-methyl-1,2,3,4,6,7,8,8a-octahydroquinolin-5-yl)heptane-2,6-dione
  参考文献：
  名称：

  Total Synthesis of (−)-Lycoperine A

  摘要：

  Lycoperine A was synthesized through a highly convergent route in which a double alkylation of 2,6-dicyano-N-benzylpiperidine with the octahydroquinoline moiety gave the lycoperine skeleton. The octahydroquinoline was prepared by a desymmetrization reaction of 5-methylcyclohexane-1,3-dione. Hydrolysis, reductive amination, and cyclization gave lycoperine A in 13 steps and 3% overall yield. The absolute configuration of lycoperine A was assigned as 6R,6'R,8R,8'R,13S,17R.

  DOI：

  10.1021/ol902389e