Tert-butyl 7-(6-formyl-1,3-benzodioxol-5-yl)-2,3-dihydroindole-1-carboxylate | 157738-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Tert-butyl 7-(6-formyl-1,3-benzodioxol-5-yl)-2,3-dihydroindole-1-carboxylate
• CAS: 157738-77-7
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: VGKMRHDSFZSCFC-UHFFFAOYSA-N

物化性质

• 沸点：
  534.0±50.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 7-(6-formyl-1,3-benzodioxol-5-yl)-2,3-dihydroindole-1-carboxylate 在 盐酸 、 silver(l) oxide 作用下， 生成 去氢石蒜碱酮
  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-3,4-亚甲基二氧苯甲醛 、 7-(tributylstannyl)-2,3-dihydroindole-1-carboxylic acid tert-butyl ester 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 以63%的产率得到Tert-butyl 7-(6-formyl-1,3-benzodioxol-5-yl)-2,3-dihydroindole-1-carboxylate
  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

文献信息

• 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.