(11S,11aS)-(-)-10,11-dihydroxy-7,8-dimethoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizin-4-one | 143724-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (11S,11aS)-(-)-10,11-dihydroxy-7,8-dimethoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizin-4-one
• CAS: 143724-56-5
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: ONKDFNSQFALBGT-HZMBPMFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  79.23
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (11S,11aS)-(-)-10,11-dihydroxy-7,8-dimethoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizin-4-one 在 三乙基硅烷 、 硝酸 、 三氟乙酸 作用下， 反应 2.0h， 生成 (+/-)-8-methoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizine-4,7,10-trione
  参考文献：
  名称：

  A Synthesis of 4-Cyano-hexahydro-2H-benzo[b]quinolizine-7,10-dione as a Simple Model Compound of Saframycin A

  摘要：

  A simple and efficient synthesis of 4-cyano-8-methoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzo[b]quinolizine-7,10-dione (20a) as a simple model compound of saframycin A (1) is described starting from the corresponding lactam (16). Reduction of the lactam (16) with lithium aluminum hydride followed by sodium cyanide treatment afforded the alpha-amino nitrile (19) as an inseparable mixture in an excellent yield. Oxidative demethylation of compound (19) with 1ON HNO3 gave the title compound (20a) and its C-4 epimer (20b). The structure of 20a was confirmed by H-1 nmr and C-13 nmr spectroscopic analysis.

  DOI：

  10.3987/com-92-6017
• 作为产物：
  描述：

  diisopropyl (S)-α-aminoadipate 在 氢氧化钾 、 sodium tetrahydroborate 、 四氯化锡 、 sodium cyanoborohydride 、 溶剂黄146 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 50.0h， 生成 (11S,11aS)-(-)-10,11-dihydroxy-7,8-dimethoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizin-4-one
  参考文献：
  名称：

  A Synthesis of 4-Cyano-hexahydro-2H-benzo[b]quinolizine-7,10-dione as a Simple Model Compound of Saframycin A

  摘要：

  A simple and efficient synthesis of 4-cyano-8-methoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzo[b]quinolizine-7,10-dione (20a) as a simple model compound of saframycin A (1) is described starting from the corresponding lactam (16). Reduction of the lactam (16) with lithium aluminum hydride followed by sodium cyanide treatment afforded the alpha-amino nitrile (19) as an inseparable mixture in an excellent yield. Oxidative demethylation of compound (19) with 1ON HNO3 gave the title compound (20a) and its C-4 epimer (20b). The structure of 20a was confirmed by H-1 nmr and C-13 nmr spectroscopic analysis.

  DOI：

  10.3987/com-92-6017