4-cyclohexyl-2-phenylquinazoline

• 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-cyclohexyl-2-phenylquinazoline
• 英文别名: 4-Cyclohexyl-2-phenyl-quinazoline
• 化学式: C₂₀H₂₀N₂
• 分子量: 288.392
• InChiKey: PZXJVBUHBNWQIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苯基亚胺苄基氯 在 四溴化碳 、 rose bengal 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 6.5h， 生成 4-cyclohexyl-2-phenylquinazoline
  参考文献：
  名称：

  Transition Metal-Free Visible Light-Driven Photoredox Oxidative Annulation of Arylamidines

  摘要：

  A fast catalytic synthesis of multisubstituted quinazolines from readily available amidines via visible light-mediated oxidative C(sp(3))-C(sp(2)) bond formation has been established. This reaction is a metal-free oxidative coupling catalyzed by a photoredox organocatalyst. The protocol features low catalyst loading (1 mol %).

  DOI：

  10.1021/acs.joc.5b02366

文献信息

• Metal-Free Oxidative Decarbonylative Coupling of Aliphatic Aldehydes with Azaarenes: Successful Minisci-Type Alkylation of Various Heterocycles
  作者：Ren-Jin Tang、Lei Kang、Luo Yang

  DOI：10.1002/adsc.201500268

  日期：2015.6.15

  A metal‐free oxidative decarbonylative coupling of aliphatic aldehydes with various electron‐deficient heterocycles has been developed. This reaction is supposed to be realized via a Minisci‐type mechanism, based on the substrate scope, regioselectivity and radical trapping experiments. The ready availability of aliphatic aldehydes, metal‐free conditions and broad substrate scope should make this method

  已经开发出脂肪族醛与各种电子不足的杂环的无金属氧化脱羰基偶联。根据底物范围，区域选择性和自由基捕获实验，该反应被认为是通过Minisci型机制实现的。脂肪醛的现成可用性，无金属条件和广泛的底物范围应使该方法对生物活性杂环的后期烷基化具有吸引力。
• Alkyl Carbazates for Electrochemical Deoxygenative Functionalization of Heteroarenes
  作者：Yongyuan Gao、Zhengguang Wu、Lei Yu、Yi Wang、Yi Pan

  DOI：10.1002/anie.202001571

  日期：2020.6.26

  work describes carbazate as a new type of electrochemically activated alkylating agent derived from ubiquitous alcohols for direct functionalization of heteroarenes under mild electrolytic conditions. The simple undivided cell at low oxidative potentials with carbon/platinum electrode set‐ups offers excellent substrate tolerance, affording a variety of primary, secondary and tertiary alkyl‐decorated

  用于醇活化的C-0键裂解在合成上是有用的，并且实际上具有挑战性。这项工作将氨基甲酸酯描述为一种新型的电化学活化的烷基化剂，其衍生自普遍存在的醇，可在温和的电解条件下将杂芳烃直接官能化。具有碳/铂电极设置的低氧化电位的简单未分割电池可提供出色的底物耐受性，可提供多种伯，仲和叔烷基修饰的杂环，并具有良好的化学收率。此外，已经研究了该电化学脱氧烷基化反应的机理。
• Direct Synthesis of Substituted Pyrimidines and Quinazolines
  作者：Mohammad Movassaghi、Matthew Hill

  DOI：10.1055/s-2007-990932

  日期：2008.3

  A variety of N-vinyl and N-aryl amides were converted in one step into the corresponding pyrimidine and quinazoline derivatives, respectively. Amide activation with trifluoromethanesulfonic anhydride in the presence of 2-chloropyridine followed by nitrile addition to the activated amide derivative and annulation provides the desired azaheterocycles.

  各种 N-乙烯基和 N-芳基酰胺在一个步骤中分别转化为相应的嘧啶和喹唑啉衍生物。在 2-氯吡啶存在下，先用三氟甲磺酸酐进行酰胺活化，然后将腈加到活化的酰胺衍生物中并环化，就得到了所需的杂杂环。
• New Strategies for the Synthesis of Pyrimidine Derivatives
  作者：Matthew D. Hill、Mohammad Movassaghi

  DOI：10.1002/chem.200800014

  日期：2008.8.8

  Recent advances in pyrimidine synthesis are described. Modification of conventional strategies involving N-C-N fragment condensation with 1,3-dicarbonyl derivatives remains a common theme in current literature. Other methods, including N-C fragment condensation strategies, provide reactive intermediates capable of intramolecular cyclization and formation of pyrimidine derivatives. These recently developed

  描述了嘧啶合成的最新进展。涉及NCN片段与1，3-二羰基衍生物缩合的常规策略的修改仍然是当前文献中的共同主题。其他方法，包括NC片段缩合策略，提供了能够分子内环化和形成嘧啶衍生物的反应性中间体。这些最近开发的方法为氮杂杂环合成提供了宝贵的补充。
• Iron‐Based Imidazolium Salt as Dual Lewis Acid and Redox Catalyst for the Aerobic Synthesis of Quinazolines
  作者：Mario Martos、Isidro M. Pastor

  DOI：10.1002/ejoc.202200839

  日期：2022.9.27

  An efficient and sustainable protocol for the preparation of quinazolines by means of a condensation-cyclization-oxidation reaction sequence promoted by an iron-imidazolium catalyst has been developed and fully assessed in terms of environmental impact.

  已经开发了一种通过铁-咪唑鎓催化剂促进的缩合-环化-氧化反应序列制备喹唑啉的有效且可持续的方案，并在环境影响方面进行了全面评估。