8-hydroxy-9,10-(methylenedioxy)-4,5-dihydropyrrolo<3,2,1-de>phenanthridin-7-one | 157738-78-8

• 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: 8-hydroxy-9,10-(methylenedioxy)-4,5-dihydropyrrolo<3,2,1-de>phenanthridin-7-one
• 英文别名: 9-Hydroxy-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9,15(19),16-hexaen-11-one
• CAS: 157738-78-8
• 化学式: C₁₆H₁₁NO₄
• 分子量: 281.268
• InChiKey: BTHPTPXMJDVRIM-UHFFFAOYSA-N

物化性质

• 沸点：
  566.2±50.0 °C(predicted)
• 密度：
  1.65±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-hydroxy-9,10-(methylenedioxy)-4,5-dihydropyrrolo<3,2,1-de>phenanthridin-7-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 40.0h， 以86%的产率得到kalbretorine
  参考文献：
  名称：

  A Synthesis of Pyrrolophenanthridone Alkaloids via Consecutive Directed Lithiation and Palladium-catalyzed Cross-coupling Reactions

  摘要：

  A short and convergent synthesis of pyrrolophenanthridone alkaloids, such as anhydrolycorin-7-one, oxoassoanine, hippadine, and pratosine, was developed by using directed lithiation and palladium-catalyzed cross-coupling as key reactions. Anhydrolycorin-7-one was converted to an antitumor alkaloid, kalbretorine, via directed lithiation and hydroxylation reactions.

  DOI：

  10.3987/com-94-6777
• 作为产物：
  描述：

  6-溴苯并[d][1,3]二氧代-5-羧酸 在 palladium on activated charcoal 2,6-二甲基吡啶 、 盐酸 、 正丁基锂 、 磺酰氯 、 草酰氯 、 双(三甲基硅基)过氧化物 、 1,1,2,2-四氟-1,2-二溴乙烷 、 硫酸 、 氢气 、 sodium methylate 、 铜 、 magnesium 作用下， 以 二氯甲烷 为溶剂， 反应 28.17h， 生成 8-hydroxy-9,10-(methylenedioxy)-4,5-dihydropyrrolo<3,2,1-de>phenanthridin-7-one
  参考文献：
  名称：

  An Oxazoline-Mediated Synthesis of the Pyrrolophenanthridine Alkaloids and Some Novel Derivatives

  摘要：

  An unsymmetrical biaryl coupling between the Grignard of N-benzyl-7-bromoindoline 25 and the appropriately substituted (o-methoxyaryl)oxazoline 15 leads to an intermediate biaryl which can be elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system. This simple two-step sequence provides general access to the pyrrolophenanthridine alkaloids 2-6.

  DOI：

  10.1021/jo951474x

文献信息

• An Oxazoline-Mediated Synthesis of the Pyrrolophenanthridine Alkaloids and Some Novel Derivatives
  作者：Richard H. Hutchings、A. I. Meyers

  DOI：10.1021/jo951474x

  日期：1996.1.1

  An unsymmetrical biaryl coupling between the Grignard of N-benzyl-7-bromoindoline 25 and the appropriately substituted (o-methoxyaryl)oxazoline 15 leads to an intermediate biaryl which can be elaborated in one step to the 1H-pyrrolo[3,2,1-de]phenanthridine ring system. This simple two-step sequence provides general access to the pyrrolophenanthridine alkaloids 2-6.
• A Synthesis of Pyrrolophenanthridone Alkaloids via Consecutive Directed Lithiation and Palladium-catalyzed Cross-coupling Reactions
  作者：Masatomo Iwao、Hirokazu Takehara、Shigeru Obata、Mitsuaki Watanabe

  DOI：10.3987/com-94-6777

  日期：——

  A short and convergent synthesis of pyrrolophenanthridone alkaloids, such as anhydrolycorin-7-one, oxoassoanine, hippadine, and pratosine, was developed by using directed lithiation and palladium-catalyzed cross-coupling as key reactions. Anhydrolycorin-7-one was converted to an antitumor alkaloid, kalbretorine, via directed lithiation and hydroxylation reactions.