(4R)-4-[(2S,3R)-3-ethenylpiperidin-2-yl]-2-methyl-9-[(2S,3S)-2-[(4R)-2-methyl-3-oxonona-1,8-dien-4-yl]piperidin-3-yl]non-1-en-3-one | 1255151-08-6

• 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: (4R)-4-[(2S,3R)-3-ethenylpiperidin-2-yl]-2-methyl-9-[(2S,3S)-2-[(4R)-2-methyl-3-oxonona-1,8-dien-4-yl]piperidin-3-yl]non-1-en-3-one
• CAS: 1255151-08-6
• 化学式: C₃₂H₅₂N₂O₂
• 分子量: 496.777
• InChiKey: QGZWIAMGPVLNDW-JMMMPTOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-4-[(2S,3R)-3-ethenylpiperidin-2-yl]-2-methyl-9-[(2S,3S)-2-[(4R)-2-methyl-3-oxonona-1,8-dien-4-yl]piperidin-3-yl]non-1-en-3-one 在 水 、 silica gel 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以49.5 mg的产率得到(1R,3R,9S,9aS)-9-[5-[(1R,3R,9R,9aS)-9-ethenyl-3-methyl-2-oxo-1,3,4,6,7,8,9,9a-octahydroquinolizin-1-yl]pentyl]-3-methyl-1-pent-4-enyl-1,3,4,6,7,8,9,9a-octahydroquinolizin-2-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)- and (+)-Petrosin

  摘要：

  The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.

  DOI：

  10.1021/ol1022257
• 作为产物：
  描述：

  (2S,3R)-N-tert-butoxycarbonyl-2-{(4R)-9-[(2S,3S)-N-tert-butoxycarbonyl-2-((4R)-2-methyl-3-oxonona-1,8-dien-4-yl)piperidin-3-yl]-2-methyl-3-oxonon-1-en-4-yl}-3-vinyl-piperidine 在 zinc dibromide 、 水 、 碳酸氢钠 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 生成 (4R)-4-[(2S,3R)-3-ethenylpiperidin-2-yl]-2-methyl-9-[(2S,3S)-2-[(4R)-2-methyl-3-oxonona-1,8-dien-4-yl]piperidin-3-yl]non-1-en-3-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)- and (+)-Petrosin

  摘要：

  The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.

  DOI：

  10.1021/ol1022257

文献信息

• Enantioselective Total Synthesis of (−)- and (+)-Petrosin
  作者：Hiroki Toya、Kentaro Okano、Kiyosei Takasu、Masataka Ihara、Atsushi Takahashi、Haruo Tanaka、Hidetoshi Tokuyama

  DOI：10.1021/ol1022257

  日期：2010.11.19

  The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.