(S)-(+/-)-10-hydroxy-7,8-dimethoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizin-4-one | 143724-57-6

• 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: (S)-(+/-)-10-hydroxy-7,8-dimethoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizin-4-one
• CAS: 143724-57-6
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: IKVDMIRKTONRLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  21.0
• 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：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-(+/-)-10-hydroxy-7,8-dimethoxy-9-methyl-1,3,4,6,11,11a-hexahydro-2H-benzoquinolizin-4-one 在 硝酸 作用下， 反应 1.0h， 以90.9%的产率得到(+/-)-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 三乙基硅烷 、 氢氧化钾 、 sodium tetrahydroborate 、 四氯化锡 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 、 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 51.0h， 生成 (S)-(+/-)-10-hydroxy-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

文献信息

• A Synthesis of 4-Cyano-hexahydro-2H-benzo[b]quinolizine-7,10-dione as a Simple Model Compound of Saframycin A
  作者：Akinori Kubo、Tatsuya Nakai、Yuichi Koizumi、Naoki Saito、Yuzuru Mikami、Katsukiyo Yazawa、Jun Uno

  DOI：10.3987/com-92-6017

  日期：——

  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.