2-(cyclohexylamino)quinazolin-4(3H)-one | 1791-52-2

• 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-(cyclohexylamino)quinazolin-4(3H)-one
• 英文别名: 2-cyclohexylamino-3H-quinazolin-4-one；2-(cyclohexylamino)-3H-quinazolin-4-one
• CAS: 1791-52-2
• 化学式: C₁₄H₁₇N₃O
• 分子量: 243.308
• InChiKey: IQZOWJQOCNCUAC-UHFFFAOYSA-N

物化性质

• 熔点：
  209-211 °C
• 沸点：
  406.1±28.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  异氰环已烷 、 2-氨基苯甲酰胺 在 过氧化氢异丙苯 、 碘 作用下， 以 甲基叔丁基醚 为溶剂， 反应 2.0h， 以92%的产率得到2-(cyclohexylamino)quinazolin-4(3H)-one
  参考文献：
  名称：

  I2/CHP 介导的 2-氨基苯甲酰胺和异氰化物的氧化偶联：获得 2-氨基喹唑啉酮

  摘要：

  由 I2 和枯基氢过氧化物 (CHP) 介导的 2-氨基苯甲酰胺 1 和异氰化物 2 的氧化偶联导致以中等至极好的产率形成 2-氨基喹唑啉酮 3。该方法提供了一种在无金属条件下通过两个 C-N 键形成反应制备具有高原子经济性的 2-氨基喹唑啉酮的有效方法。产物可进一步转化为苯并[4,5]咪唑并[2,1-b]喹唑啉-12(6H)-one (4)。

  DOI：

  10.1002/ejoc.201600876

文献信息

• Odorless Isocyanide Chemistry: An Integrated Microfluidic System for a Multistep Reaction Sequence
  作者：Siddharth Sharma、Ram Awatar Maurya、Kyoung-Ik Min、Guan-Young Jeong、Dong-Pyo Kim

  DOI：10.1002/anie.201303213

  日期：2013.7.15

  continuous‐flow microfluidic setup enables in situ generation, extraction, separation, and reaction of foul‐smelling isocyanides with little exposure to the surroundings. Isocyanides were generated by dehydration of the corresponding N‐substituted formamides, and several representative isocyanide‐based organic reactions were successfully performed. DIPEA=N,N‐diisopropylethylamine.

  不能闻到：集成的连续流微流控装置可在几乎不暴露于环境的情况下原位产生，提取，分离异味异氰酸酯并进行反应。异氰酸酯是由相应的N-取代的甲酰胺脱水生成的，成功地进行了几种基于异氰酸酯的代表性有机反应。DIPEA = N，N-二异丙基乙胺。
• Electrochemical Synthesis of Carbodiimides via Metal/Oxidant-Free Oxidative Cross-Coupling of Amines and Isocyanides
  作者：Bhanwar Kumar Malviya、Pradeep K. Jaiswal、Ved Prakash Verma、Satpal Singh Badsara、Siddharth Sharma

  DOI：10.1021/acs.orglett.0c00510

  日期：2020.3.20

  This work discloses an electrochemical oxidative cross-coupling of amines with aryl and aliphatic isocyanides. In an undivided cell, the reaction proceeds without involving any transition-metal catalyst, oxidant, or toxic reagents providing carbodiimides in good yields, thereby circumventing stoichiometric chemical oxidants, with H2 as the only byproduct. Moreover, carbodiimides were in situ converted

  这项工作公开了胺与芳基和脂族异氰酸酯的电化学氧化交叉偶联。在一个没有分隔的电池中，反应进行时不涉及任何过渡金属催化剂，氧化剂或有毒的试剂，以高收率提供了碳二亚胺，从而绕开了化学计量的化学氧化剂，其中H 2是唯一的副产物。此外，使用电开-关策略可将碳二亚胺原位转化为中等至良好收率的不对称脲。
• A concise and efficient solid-phase synthesis of 2-amino-4(3H)-quinazolinones
  作者：Rui-Yang Yang、Alan Kaplan

  DOI：10.1016/s0040-4039(00)01201-6

  日期：2000.9

  A concise and efficient solid-phase synthesis of 2-amino-4(3H)-quinazolinones is described. Reaction of polymer-bound isothiourea with isatoic anhydride provides 2-amino-4(3H)-quinazolinones with good yields and excellent purity.

  描述了2-氨基-4（3 H）-喹唑啉酮的简洁有效的固相合成。聚合物结合的异硫脲与异丙基酸酐的反应以良好的收率和优异的纯度提供了2-氨基-4（3 H）-喹唑啉酮。
• Continuous Recycling of Homogeneous Pd/Cu Catalysts for Cross-Coupling Reactions
  作者：Siddharth Sharma、K. C. Basavaraju、Ajay K. Singh、Dong-Pyo Kim

  DOI：10.1021/ol501802w

  日期：2014.8.1

  Given the importance of homogeneous catalysts recycling in organic chemistry, we have developed a unique microfluidic loop system for automated continuous recirculation of a soluble polymer supported metal catalyst for novel isocyanide cross-coupling reactions under thermomorphic multicomponent solvent (TMS) conditions. Our system provides an innovative approach for the chemical library synthesis of quinazolinone derivatives as well as an important intermediate of Merck's LTD4 antagonist "Singulair" with efficient continuous homogeneous catalyst recycling.
• Ligand-free palladium assisted insertion of isocyanides to urea derivatives for cascade synthesis of phenylamino-substituted quinazolinones
  作者：Siddharth Sharma、Abhilasha Jain

  DOI：10.1016/j.tetlet.2014.09.027

  日期：2014.10

  Palladium catalyzed cascade coupling of substituted urea derivatives and tert-butyl isocyanide for the efficient synthesis of phenylamino-substituted quinazolinones has been developed in moderate to good yields. This method provides a short and alternative approach for the synthesis of quinazolinones derivatives which are valuable compounds with biological and pharmacological potentials. A plausible mechanistic scheme is proposed. (C) 2014 Elsevier Ltd. All rights reserved.