1,3-Dimethyl-4-phenyl-6-piperidin-1-ylpyrazolo[3,4-d]pyrimidine | 1216866-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1,3-Dimethyl-4-phenyl-6-piperidin-1-ylpyrazolo[3,4-d]pyrimidine
• CAS: 1216866-04-4
• 化学式: C₁₈H₂₁N₅
• 分子量: 307.398
• InChiKey: NVKOTQNHVZWNLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-((1,3-dimethyl-1H-pyrazol-5-ylimino)(piperidin-1-yl)methyl)benzamide 反应 0.25h， 以92%的产率得到1,3-Dimethyl-4-phenyl-6-piperidin-1-ylpyrazolo[3,4-d]pyrimidine
  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.