9-hydroxy-10-methoxy-2,3-methylenedioxybenzo[c]phenanthridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-hydroxy-10-methoxy-2,3-methylenedioxybenzo[c]phenanthridine
• 英文别名: zanthoxyline；4-Methoxy-[1,3]benzodioxolo[5,6-c]phenanthridin-3-ol
• 化学式: C₁₉H₁₃NO₄
• 分子量: 319.317
• InChiKey: FYJSYMQIPQSCAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-hydroxy-10-methoxy-2,3-methylenedioxybenzo[c]phenanthridine 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 25.5h， 生成 5,6-dihydro-9,10-dimethoxy-N-methyl-2,3-methylenedioxybenzo[c]phenanthridine
  参考文献：
  名称：

  微波辅助氮杂6π电子体系的环化反应和布鲁索帕比林的结构修饰，全合成苯并[ c ]菲啶生物碱

  摘要：

  合成了苯并[ c ]菲啶生物碱1a - f和19和苯并[ c ]菲啶生物碱，白屈菜红碱（2d）和布鲁索帕林（2f）的des- N-甲基（nor）型。关键步骤是利用微波辅助的2-环烯基苯甲醛肟基甲基醚4作为氮杂6π电子体系的微波辅助反应，构建四环10,11-二氢苯并[ c ]菲啶，该过程分两步从Suzuki- 2-溴苯甲醛6的宫浦交叉偶联反应与2-（3,4-二氢-6,7-亚甲基二氧基萘基）硼酸频哪醇酯7。另外，确定了溴索品比林（2f）（2,3,9,10-四加氧型）的确切结构为白屈菜红碱（2d）。

  DOI：

  10.1016/j.tet.2010.11.066
• 作为产物：
  描述：

  2,3-二羟基萘 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 硝酸 、 palladium diacetate 、 乙酸酐 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三苯基膦 、 cesium fluoride 、 silver carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 9-hydroxy-10-methoxy-2,3-methylenedioxybenzo[c]phenanthridine
  参考文献：
  名称：

  Synthesis of 2,3,9,10-Tetraoxygenated Benzo[c]phenanthridine Derivatives via Palladium-Mediated Aryl-Aryl Coupling Reaction

  摘要：

  Two 2,3,9,10-tetraoxygenated benzo[c]phenanthridine alkaloids, 1 2, originally reported as zanthoxyline and broussonpapyrine, respectively, were synthesized using the Pd-mediated intramolecular aryl-aryl coupling reaction as the key step.

  DOI：

  10.3987/com-15-s(t)56

文献信息

• Benzophenanthridine alkaloids from Zanthoxylum rhoifolium
  作者：Neusa F. de Moura、Heraldo B. Ribeiro、Emília C.S. Machado、Eduardo M. Ethur、Nilo Zanatta、Ademir F. Morel

  DOI：10.1016/s0031-9422(97)00498-6

  日期：1997.12

  A novel benzophenanthridine alkaloid, named zanthoxyline, was isolated from the bark of Zanthoxylum rhoifolium, together with the known compounds, dihydronitidine, 6-oxynitidine and skimmianine. The structure of the new compound was elucidated on the basis of spectroscopic investigations and elemental analysis. (C) 1997 Elsevier Science Ltd.
• Synthesis of Zanthoxyline and Its Related Compounds: Revision of the Reported Structure
  作者：Hitoshi Abe、Takashi Harayama、Naoko Kobayashi、Yasuo Takeuchi

  DOI：10.3987/com-09-s(s)111

  日期：——

  Benzo[c]phenanthridine alkaloid, zanthoxyline, was synthesized through an intramolecular biaryl coupling reaction of N-naphthylbenzamide derivative using a palladium reagent. Comparison of the NMR data for the synthetic product with that reported previously revealed that the proposed structure was incorrect. Synthesis of the related compounds suggested that the correct structure of zanthoxyline is the previously known decarine.
• Synthesis of 2,3,9,10-Tetraoxygenated Benzo[c]phenanthridine Derivatives via Palladium-Mediated Aryl-Aryl Coupling Reaction
  作者：Hitoshi Abe、Naoko Kobayashi、Yutaka Kadoshima、Yasuo Takeuchi、Takashi Harayama、Yoshikazu Horino

  DOI：10.3987/com-15-s(t)56

  日期：——

  Two 2,3,9,10-tetraoxygenated benzo[c]phenanthridine alkaloids, 1 2, originally reported as zanthoxyline and broussonpapyrine, respectively, were synthesized using the Pd-mediated intramolecular aryl-aryl coupling reaction as the key step.
• Total synthesis of benzo[c]phenanthridine alkaloids based on a microwave-assisted electrocyclic reaction of the aza 6π-electron system and structural revision of broussonpapyrine
  作者：Yuhsuke Ishihara、Shuhei Azuma、Tominari Choshi、Kakujirou Kohno、Kanako Ono、Hiroyuki Tsutsumi、Takashi Ishizu、Satoshi Hibino

  DOI：10.1016/j.tet.2010.11.066

  日期：2011.2

  Total syntheses of the des-N-methyl (nor) type of benzo[c]phenanthridine alkaloids 1a–f and 19 and benzo[c]phenanthridine alkaloids, chelerythrine (2d), and broussonpapyrine (2f) were achieved. The key step was the construction of tetracyclic 10,11-dihydrobenzo[c]phenanthridines using a microwave-assisted electrocyclic reaction of the 2-cycloalkenylbenzaldoxime methyl ether 4 as an aza 6π-electron

  合成了苯并[ c ]菲啶生物碱1a - f和19和苯并[ c ]菲啶生物碱，白屈菜红碱（2d）和布鲁索帕林（2f）的des- N-甲基（nor）型。关键步骤是利用微波辅助的2-环烯基苯甲醛肟基甲基醚4作为氮杂6π电子体系的微波辅助反应，构建四环10,11-二氢苯并[ c ]菲啶，该过程分两步从Suzuki- 2-溴苯甲醛6的宫浦交叉偶联反应与2-（3,4-二氢-6,7-亚甲基二氧基萘基）硼酸频哪醇酯7。另外，确定了溴索品比林（2f）（2,3,9,10-四加氧型）的确切结构为白屈菜红碱（2d）。