N-((1H-indol-6-ylimino)(piperidin-1-yl)methyl)benzamide | 1216865-95-0

• 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: N-((1H-indol-6-ylimino)(piperidin-1-yl)methyl)benzamide
• 英文别名: N-[N-(1H-indol-6-yl)-C-piperidin-1-ylcarbonimidoyl]benzamide
• CAS: 1216865-95-0
• 化学式: C₂₁H₂₂N₄O
• 分子量: 346.432
• InChiKey: FLFDBUSKEPKPKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  60.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-((1H-indol-6-ylimino)(piperidin-1-yl)methyl)benzamide 反应 0.25h， 以82%的产率得到9-phenyl-7-(piperidin-1-yl)-1H-pyrrolo[2,3-f]quinazoline
  参考文献：
  名称：

  Swift and Efficient Synthesis of 4-Phenylquinazolines: Involvement of N-Heterocyclic Carbene in the Key Cyclization Step

  摘要：

  An original route to 2-alkyamino-4-phenylquinazolines in three steps from simple (hetero)aromatic amines is reported here. The key step involves the intramolecular cyclization of benzoyl arylguanidines performed in [OMIm]Cl ionic liquid. The basic (hetero)aromatic guanidines deprotonate the imidazolium-based Ionic liquid, thus triggering the cascade process ultimately leading to the intramolecular cyclization. This reaction is the first example of a Friedel-Crafts-type reaction in which an N-heterocyclic carbene is involved in the formation of the electrophilic intermediate.

  DOI：

  10.1021/jo902726k
• 作为产物：
  描述：

  哌啶 、 N-(1H-indol-6-ylcarbamothioyl)benzamide 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-((1H-indol-6-ylimino)(piperidin-1-yl)methyl)benzamide
  参考文献：
  名称：

  Swift and Efficient Synthesis of 4-Phenylquinazolines: Involvement of N-Heterocyclic Carbene in the Key Cyclization Step

  摘要：

  An original route to 2-alkyamino-4-phenylquinazolines in three steps from simple (hetero)aromatic amines is reported here. The key step involves the intramolecular cyclization of benzoyl arylguanidines performed in [OMIm]Cl ionic liquid. The basic (hetero)aromatic guanidines deprotonate the imidazolium-based Ionic liquid, thus triggering the cascade process ultimately leading to the intramolecular cyclization. This reaction is the first example of a Friedel-Crafts-type reaction in which an N-heterocyclic carbene is involved in the formation of the electrophilic intermediate.

  DOI：

  10.1021/jo902726k

文献信息

• Swift and Efficient Synthesis of 4-Phenylquinazolines: Involvement of <i>N</i>-Heterocyclic Carbene in the Key Cyclization Step
  作者：Julien Debray、Jean-Marc Lévêque、Christian Philouze、Micheline Draye、Martine Demeunynck

  DOI：10.1021/jo902726k

  日期：2010.3.19

  An original route to 2-alkyamino-4-phenylquinazolines in three steps from simple (hetero)aromatic amines is reported here. The key step involves the intramolecular cyclization of benzoyl arylguanidines performed in [OMIm]Cl ionic liquid. The basic (hetero)aromatic guanidines deprotonate the imidazolium-based Ionic liquid, thus triggering the cascade process ultimately leading to the intramolecular cyclization. This reaction is the first example of a Friedel-Crafts-type reaction in which an N-heterocyclic carbene is involved in the formation of the electrophilic intermediate.