6-methyl-4-phenyl-2-(piperidin-1-yl)quinazoline | 307329-79-9

• 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: 6-methyl-4-phenyl-2-(piperidin-1-yl)quinazoline
• 英文别名: 6-methyl-4-phenyl-2-piperidin-1-ylquinazoline
• CAS: 307329-79-9
• 化学式: C₂₀H₂₁N₃
• mdl: MFCD00548181
• 分子量: 303.407
• InChiKey: VTDHRTNZHVPWDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.3
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-((piperidin-1-yl)(p-tolylimino)methyl)benzamide 反应 0.25h， 以79%的产率得到6-methyl-4-phenyl-2-(piperidin-1-yl)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

文献信息

• Copper-Catalyzed Domino Three-Component Approach for the Assembly of 2-Aminated Benzimidazoles and Quinazolines
  作者：Lam Quang Tran、Jihui Li、Luc Neuville

  DOI：10.1021/acs.joc.5b00614

  日期：2015.6.19

  A copper-promoted three-component synthesis of 2-aminobenzimidazoles (1) or of 2-aminoquinazolines (2) involving cyanamides, arylboronic acids, and amines has been developed. The operationally simple oxidative process, performed in the presence of K2CO3, a catalytic amount of CuCl2·2H2O, 2,2′-bipyridine, and an O2 atmosphere (1 atm), allows the rapid assembly of either benzimidazoles or quinazolines

  已经开发了一种铜促进的三组分合成2-氨基苯并咪唑（1）或2-氨基喹唑啉（2）的方法，该方法涉及氰胺，芳基硼酸和胺。在K 2 CO 3，催化量的CuCl 2 ·2H 2 O，2,2'-联吡啶和O 2气氛（1个大气压）的存在下进行的操作简单的氧化过程可以使任何一种的快速组装分别从芳基或苄基取代的氰胺开始的苯并咪唑或喹唑啉。在这个过程中，铜促进了三个键，两个C–N键以及一个由CH–H功能化事件产生的额外键的形成。
• Copper(II) Acetate/Oxygen-Mediated Nucleophilic Addition and Intramolecular CH Activation/CN or CC Bond Formation: One-Pot Synthesis of Benzimidazoles or Quinazolines
  作者：Hua-Feng He、Zhi-Jing Wang、Weiliang Bao

  DOI：10.1002/adsc.201000469

  日期：2010.11.22

  Diarylcarbodiimides or benzylphenylcarbodiimides are converted to 1,2-disubstituted benzimidazoles or 1,2-disustituted quinazolines via addition/intramolecular CH bond activation/C-N or CC bond forming reaction using copper(II) acetate/oxygen [Cu(OAc)2/O2] as the oxidant at 100 °C in one-pot cascade procedure.

  使用乙酸铜（II）/氧[Cu（OAc）2 / O 2）通过加成/分子内CH键活化/ CN或CC键形成反应将二芳基碳二亚胺或苄基苯基碳二亚胺转化为1,2-二取代的苯并咪唑或1,2-取代的喹唑啉以一锅级联程序在100°C下作为氧化剂。
• A catalyst- and solvent-free selective approach to biologically important quinazolines and benzo[g]quinazoline
  作者：Vipan Kumar、Chander Mohan、Manish Gupta、Mohinder P. Mahajan

  DOI：10.1016/j.tet.2005.01.118

  日期：2005.4

  A solvent-free and catalyst-free approach towards the selective synthesis of quinazolines and benzo[g] quinazolines has been developed using conventional microwave oven with excellent yields and reproducibilty. (c) 2005 Elsevier Ltd. All rights reserved.
• Quinazolines revisited: search for novel anxiolytic and GABAergic agents
  作者：R.K. Goel、Vipan Kumar、M.P. Mahajan

  DOI：10.1016/j.bmcl.2005.02.023

  日期：2005.4

  A systematic approach through computer assisted design to identify novel quinazolines having anxiolytic and GABAergic activity has been reported. (c) 2005 Elsevier Ltd. All rights reserved.
• 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.