petrosin | 1255505-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: petrosin
• 英文别名: (1R,7S,9S,15R,21S,23S,29R,30R)-9,23-dimethyl-11,25-diazapentacyclo[19.7.1.17,11.025,29.015,30]triacontane-8,22-dione
• CAS: 1255505-30-6
• 化学式: C₃₀H₅₀N₂O₂
• 分子量: 470.739
• InChiKey: OCNVVYBTRKWBCO-JUZPTULESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  petrosin 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以57%的产率得到(1R,2S,41R,7aR,12aS,12a1R,13R,14S,19aR,24aS)-2,14-dimethyltetracosahydro-1H,5H,8H,13H-cyclohexadeca[1,2,3-ij:9,10,11-i'j']diquinolizine-1,13-diol
  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：

  在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 petrosin
  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.