4-methyl-2-pentylquinazoline | 1239313-40-6

• 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: 4-methyl-2-pentylquinazoline
• 英文别名: 4-Methyl-2-pentylquinazoline
• CAS: 1239313-40-6
• 化学式: C₁₄H₁₈N₂
• 分子量: 214.31
• InChiKey: WIZSZXKGPAMLDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2'-(hexylideneamino)acetophenone oxime 以 乙腈 为溶剂， 以78%的产率得到4-methyl-2-pentylquinazoline
  参考文献：
  名称：

  An efficient synthesis of quinazolines: a theoretical and experimental study on the photochemistry of oxime derivatives

  摘要：

  A new photochemical method for the preparation of quinazolines (2) through irradiation of [2-(methyleneamino)phenyl]methanone oximes (1) is reported. The photoreaction has been studied in depth by experimental, theoretical and photochemical methods. A six-electron electrocyclic ring closure mechanism, followed by water loss, is proposed and rationalized to explain the formation of quinazolines (2). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.082

文献信息

• Hydrogen peroxide-mediated synthesis of 2,4-substituted quinazolines <i>via</i> one-pot three-component reactions under metal-free conditions
  作者：Khang H. Trinh、Khang X. Nguyen、Phuc H. Pham、Tung T. Nguyen、Anh N. Q. Phan、Nam T. S. Phan

  DOI：10.1039/d0ra05040g

  日期：——

  An efficient metal-free synthesis of 2,4-substituted quinazolines via a hydrogen peroxide-mediated one-pot three-component reaction of 2-aminoaryl ketones, aldehydes, and ammonium acetate has been developed. The transformation proceeded readily under mild conditions in the presence of commercially available hydrogen peroxide. The significant advantages of this approach are (1) the readily available

  2,4-取代喹唑啉的高效无金属合成已经开发了过氧化氢介导的 2-氨基芳基酮、醛和乙酸铵的一锅三组分反应。在市售过氧化氢存在的温和条件下，转化很容易进行。这种方法的显着优点是（1）容易获得的原子效率和绿色过氧化氢作为氧化剂；(2)不需要过渡金属催化剂；(3) 反应条件温和；(4)基材范围广。据我们所知，利用过氧化氢作为一种原子效率高的绿色氧化剂来合成 2,4-取代的喹唑啉，以前没有文献报道过。该方法是对先前合成 2,4-取代喹唑啉的协议的补充。
• Synthesis of Quinazoline and Quinazolinone Derivatives via Ligand-Promoted Ruthenium-Catalyzed Dehydrogenative and Deaminative Coupling Reaction of 2-Aminophenyl Ketones and 2-Aminobenzamides with Amines
  作者：Pandula T. Kirinde Arachchige、Chae S. Yi

  DOI：10.1021/acs.orglett.9b01082

  日期：2019.5.3

  highly selective for the dehydrogenative coupling reaction of 2-aminophenyl ketones with amines to form quinazoline products. The deaminative coupling reaction of 2-aminobenzamides with amines led to the efficient formation of quinazolinone products. The catalytic coupling method provides an efficient synthesis of quinazoline and quinazolinone derivatives without using any reactive reagents or forming

  发现原位形成的钌催化体系（[Ru] / L）对2-氨基苯基酮与胺的脱氢偶联反应形成喹唑啉产物具有高度选择性。2-氨基苯甲酰胺与胺的脱氨基偶联反应导致喹唑啉酮产物的有效形成。催化偶合方法可有效合成喹唑啉和喹唑啉酮衍生物，而无需使用任何反应性试剂或形成任何有毒副产物。
• Visible-light photocatalyzed C–N bond activation of tertiary amines: a three-component approach to synthesize quinazolines
  作者：Ajithkumar Arumugam、Gopal Chandru Senadi

  DOI：10.1039/d3ob02067c

  日期：——

  three-component approach has been developed to prepare 2,4-disubstituted quinazolines from o-acylanilines, trialkylamines and ammonium chloride under visible-light using eosin Y as the photocatalyst. The notable features of this work include (i) the use of tertiary amines as an alkyl synthon and triethanolamine as a C2-OH synthon; (ii) good functional group tolerance with 52%–98% yields; (iii) proof of

  开发了一种无金属三组分方法，以曙红 Y 作为光催化剂，在可见光下由邻酰基苯胺、三烷基胺和氯化铵制备 2,4-二取代喹唑啉。这项工作的显着特点包括（i）使用叔胺作为烷基合成子和三乙醇胺作为C 2 -OH合成子； (ii) 良好的官能团耐受性，产率 52%–98%； (iii) 以邻氨基苯甲醛为底物传递 2-甲基喹唑啉3pa的概念验证； (iv)化合物3ga 、 3ja和3ma的克级合成。基于控制研究和氧化还原电位值，提出了还原猝灭机制。
• An efficient synthesis of quinazolines: a theoretical and experimental study on the photochemistry of oxime derivatives
  作者：Rafael Alonso、Alegría Caballero、Pedro J. Campos、Diego Sampedro、Miguel A. Rodríguez

  DOI：10.1016/j.tet.2010.04.082

  日期：2010.6

  A new photochemical method for the preparation of quinazolines (2) through irradiation of [2-(methyleneamino)phenyl]methanone oximes (1) is reported. The photoreaction has been studied in depth by experimental, theoretical and photochemical methods. A six-electron electrocyclic ring closure mechanism, followed by water loss, is proposed and rationalized to explain the formation of quinazolines (2). (C) 2010 Elsevier Ltd. All rights reserved.