9-hydroxy-6,7-dimethoxy-8-methyl-1,2,3,5,10,10a-hexahydrobenzindolizin-3-one | 175228-22-5

• 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: 9-hydroxy-6,7-dimethoxy-8-methyl-1,2,3,5,10,10a-hexahydrobenzindolizin-3-one
• 英文别名: 9-hydroxy-6,7-dimethoxy-8-methyl-2,5,10,10a-tetrahydro-1H-pyrrolo[1,2-b]isoquinolin-3-one
• CAS: 175228-22-5
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: BXDQMMFQIPXNDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  9-hydroxy-6,7-dimethoxy-8-methyl-1,2,3,5,10,10a-hexahydrobenzindolizin-3-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 6,7-Dimethoxy-8-methyl-1,2,3,5,10,10a-hexahydro-pyrrolo[1,2-b]isoquinolin-9-ol
  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：

  racemic diisopropyl glutamate 在 三乙基硅烷 、 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 、 三氟乙酸 为溶剂， 反应 28.0h， 生成 9-hydroxy-6,7-dimethoxy-8-methyl-1,2,3,5,10,10a-hexahydrobenzindolizin-3-one
  参考文献：
  名称：

  A Synthesis of the Derivative of 1,2,3,5,10,10a-Hexahydrobenz[f]indolizine-6,9-dione Having Antifungal Activity as a Simple Model of SaframycinA

  摘要：

  A simple and efficient synthesis of 1,2,3,5,10,10a-hexahydrobenz[f]indolizine-6,9-dione (7) and its analogs (28-30) is described starting from the corresponding lactam (15b).

  DOI：

  10.3987/com-94-s5-1

文献信息

• A Synthesis of the Derivative of 1,2,3,5,10,10a-Hexahydrobenz[f]indolizine-6,9-dione Having Antifungal Activity as a Simple Model of SaframycinA
  作者：Akinori Kubo、Tatsuya Nakai、Yuichi Koizumi、Yoshiyasu Kitahara、Naoki Saito、Yuzuru Mikami、Katsukiyo Yazawa、Jun Uno

  DOI：10.3987/com-94-s5-1

  日期：——

  A simple and efficient synthesis of 1,2,3,5,10,10a-hexahydrobenz[f]indolizine-6,9-dione (7) and its analogs (28-30) is described starting from the corresponding lactam (15b).
• 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.