2-(benzylamino)-3-phenylquinazolin-4(3H)-one | 146849-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(benzylamino)-3-phenylquinazolin-4(3H)-one
• 英文别名: 4(3H)-Quinazolinone, 3-phenyl-2-[(phenylmethyl)amino]-；2-(benzylamino)-3-phenylquinazolin-4-one
• CAS: 146849-70-9
• 化学式: C₂₁H₁₇N₃O
• 分子量: 327.385
• InChiKey: IKDFWTAPDHAOAL-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C(Solv: dichloromethane (75-09-2); ethyl ether (60-29-7))
• 沸点：
  515.7±43.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 2-(triphenylphosphoranylidene-amino)benzoate 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-(benzylamino)-3-phenylquinazolin-4(3H)-one
  参考文献：
  名称：

  A Facile and Selective Synthesis of 2-Alkylamino-4(3H)-quinazolinones

  摘要：

  The carbodiimides 2, obtained from aza-Wittig reactions of iminophosphorane 1 with aromatic isocyanates, reacted with aliphatic primary amines to give mainly 2-alkylamino-4(3H)-quinazolinones 4 with unusual selectivity.

  DOI：

  10.1081/scc-120022173

文献信息

• RE[N(SiMe₃)₂]₃-Catalyzed Guanylation/Cyclization of Amino Acid Esters and Carbodiimides
  作者：Chengrong Lu、Chao Gong、Bei Zhao、Lijuan Hu、Yingming Yao

  DOI：10.1021/acs.joc.7b02550

  日期：2018.2.2

  The example of rare-earth metal-catalyzed guanylation/cyclization of amino acid esters and carbodiimides is well-established, forming 4(3H)-2-alkylaminoquinazolinones in 65–96% yields. The rare-earth metal amides RE[N(TMS)2]3 (RE = Y, Yb, Nd, Sm, La; TMS = SiMe3) showed high activities, and La[N(TMS)2]3 performed best for a wide scope of the substrates.

  稀土金属催化氨基酸酯和碳二亚胺的鸟苷酸化/环化的例子是公认的，以65-96％的产率形成4（3 H）-2-烷基氨基喹唑啉酮。稀土金属酰胺RE [N（TMS）2 ] 3（RE = Y，Yb，Nd，Sm，La; TMS = SiMe 3）表现出高活性，而La [N（TMS）2 ] 3表现最好。广泛的基材。
• Molybdenum-mediated synthesis of quinazolin-4(3H)-ones via cyclocarbonylation using microwave irradiation
  作者：Bryan Roberts、David Liptrot、Tim Luker、Michael J. Stocks、Catherine Barber、Nicola Webb、Robert Dods、Barrie Martin

  DOI：10.1016/j.tetlet.2011.05.052

  日期：2011.7

  A new, efficient and practical synthesis of quinazolin-4(3H)-ones is reported via molybdenum-mediated cyclocarbonylation using microwave irradiation. These methods allow access to a wide range of quinazolin-4(314)-ones in reasonable yields without the need for gaseous carbon monoxide and palladium catalysts. A range of reactions illustrating the wide scope of this chemistry was carried out and all proceeded in reasonable yields. (C) 2011 Elsevier Ltd. All rights reserved.