N-(4-chlorophenyl)-4-phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 330453-93-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-chlorophenyl)-4-phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: N-(4-chlorophenyl)-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide；6-methyl-2(1H)-oxo-4-phenyl-3,4-dihydropyrimidine-5-(4'-chlorophenyl)carboxamide；N-(4-chlorophenyl)-6-methyl-2-oxo-4-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 330453-93-5
• 化学式: C₁₈H₁₆ClN₃O₂
• 分子量: 341.797
• InChiKey: QWMNGZVYFIXETH-UHFFFAOYSA-N

物化性质

• 熔点：
  265-266 °C
• 沸点：
  545.5±50.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-4-phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 以 乙腈 为溶剂， 反应 4.5h， 以89%的产率得到N-(4-chlorophenyl)-6-methyl-2-oxo-4-phenyl-1,2-dihydropyrimidine-5-carboxamide
  参考文献：
  名称：

  光诱导的2-氧-1,2,3,4-四氢嘧啶-5-羧酰胺的脱氢反应

  摘要：

  通过将各种2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides（THPMs）暴露于紫外光下，研究其光敏性，以阐明位于4-上的取代基的性质的影响。杂环的5-位和氧气或氩气气氛对反应速率的影响。在氩气下的反应速率比在氧气下的反应速率更快，并且受THPM环4和5位上取代基的性质影响。此外，发现THPM-酰胺的脱氢比相应的5-乙氧基羰基-和5-乙酰基-THPM的脱氢更快。与溶液光化学相反，通过固态照射没有观察到变化。

  DOI：

  10.1007/s13738-012-0097-0
• 作为产物：
  描述：

  对氯苯胺 以 乙醇 、 甲苯 为溶剂， 生成 N-(4-chlorophenyl)-4-phenyl-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  Targeting Dormant Tuberculosis Bacilli: Results for Molecules with a Novel Pyrimidone Scaffold

  摘要：

  Our inability to completely control TB has been due in part to the presence of dormant mycobacteria. This also renders drug regimens ineffective and is the prime cause of the appearance of drug‐resistant strains. In continuation of our efforts to develop novel antitubercular agents that especially target dormant mycobacteria, a set of 55 new compounds belonging to the pyrimidone class were designed on the basis of CoMFA and CoMSIA studies, and these were synthesized and subsequently tested against both the dormant and virulent BCG strain of M. tuberculosis. Some novel compounds have been identified which selectively inhibit the dormant tuberculosis bacilli with significantly low IC50 values. This study reports the second molecule after TMC‐207, having the ability to inhibit tuberculosis bacilli exclusively in its dormant phase. The synthesis was accomplished by a modified multicomponent Biginelli reaction. A classification model was generated using the binary QSAR approach – recursive partitioning (RP) to identify structural characteristics related to the activity. Physicochemical, structural, topological, connectivity indices, and E‐state key descriptors were used for generation of the decision tree. The decision tree could provide insights into structure–activity relationships that will guide the design of more potent inhibitors.

  DOI：

  10.1111/cbdd.12373

文献信息

• Synthesis of 3,4-Dihydropyrimidin-2(1H)-one-5-carboxamides
  作者：Mousa Soleymani、Hamid Reza Memarian

  DOI：10.1515/znb-2010-0408

  日期：2010.4.1

  The synthesis of various dihydropyrimidinone derivatives bearing carbamoyl moieties in 5-position under reflux conditions and microwave irradiation is described. An efficient three-component Biginelli reaction using catalytic amounts of zirconium(IV) chloride as an efficient catalyst leads to the formation of these compounds.

  在回流条件和微波辐射下合成了带有5位羰基基团的各种二氢嘧啶酮衍生物。使用催化量的四氯化锆作为高效催化剂进行高效的三组分Biginelli反应，导致这些化合物的形成。
• A General, Effcient and Green Procedure for Synthesis of Dihydropyrimidine-5-carboxamides in Low Melting Betaine Hydrochloride/Urea Mixture
  作者：Peng Liu、Jianwu Hao、Zhanhui Zhang

  DOI：10.1002/cjoc.201500862

  日期：2016.6

  A simple, facile and convenient strategy has been developed for the synthesis of dihydropyrimidine‐5‐carboxamides in low melting mixture of betaine hydrochloride/urea. In this procedure, the low melting mixture of betaine hydrochloride/urea plays a triple role: as a catalyst, solvent and reactant. The present green protocol has advantages such as high yield of products, short reaction times, operational

  已经开发了一种简单，简便，方便的策略，用于在甜菜碱盐酸盐/尿素的低熔点混合物中合成二氢嘧啶-5-羧酰胺。在此过程中，甜菜碱盐酸盐/尿素的低熔点混合物起着三重作用：作为催化剂，溶剂和反应物。当前的绿色方案具有以下优点：产品产量高，反应时间短，操作简便，无需色谱分离，生态友好以及适用于大规模合成。
• Synthesis of Biginelli Compounds Using Cobalt Hydrogen Sulfate
  作者：Hamid Reza Memarian、Mahnaz Ranjbar

  DOI：10.1002/jccs.201190016

  日期：2011.8

  Efficient synthesis of various 2‐oxo(thioxo)‐1,2,3,4‐tetrahydropyrimidines containing acetyl, carboethoxy, carbomethoxy and carboxamide groups on 5‐position of the N1‐substituted and N1‐unsubstituted heterocyclic ring was achieved using cobalt hydrogen sulfate Co(HSO4)2 under thermal conditions. Good to high yield, shorter reaction times, easy work up and simple preparation of Co(HSO4)2 are the advantages

  使用钴实现了在N 1-取代和N 1-未取代的杂环的5位上含有乙酰基，碳乙氧基，碳甲氧基和羧酰胺基团的各种2-氧代（thioxo）-1、2、3、4-四氢嘧啶的高效合成在热条件下产生硫酸氢Co（HSO 4）2。该合成方法的优点是产率高至高，反应时间短，易于后处理和制备Co（HSO 4）2简便。
• Iron-Catalyzed Vinylogous Aldol Condensation of Biginelli Products and Its Application toward Pyrido[4,3-<i>d</i>]pyrimidinones
  作者：Lianqiang Zhang、Zhiguo Zhang、Qingfeng Liu、Tongxin Liu、Guisheng Zhang

  DOI：10.1021/jo402773r

  日期：2014.3.7

  A novel iron-catalyzed vinylogous aldol condensation of Biginelli products with aryl aldehydes has been developed for the syntheses of potential bioactive (E)-6-arylvinyl-dihydropyrimidin-2(1H)-ones. These materials are valuable synthetic precursors to drug-like pyrido[4,3-d]pyrimidine derivatives. The amide group at the 5-position of the dihydropyrimidin-2(1H)-ones played an important role in the

  已经开发了一种新型的铁催化的比格内利产物与芳基醛基的乙烯基醇醛醇醛缩合反应，用于合成潜在的生物活性（E）-6-芳基乙烯基-二氢嘧啶-2（1 H）-ones。这些材料是药物样吡啶并[4,3- d ]嘧啶衍生物的有价值的合成前体。二氢嘧啶-2（1 H）-的5-位的酰胺基在乙烯基醇醛缩合反应中起重要作用。
• Ultrasound assisted dehydrogenation of 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides
  作者：Hamid R. Memarian、Mousa Soleymani

  DOI：10.1016/j.ultsonch.2010.10.006

  日期：2011.5

  Dehydrogenation of various 2-oxo-1,2,3.4-tetrahydropyrimidine-5-carboxamides (THPMs) to 2-oxo-1,2-dihydropyrimidine-5-carboxamides (DHPMs) using tetrabutylammonium peroxydisulfate (TBAPS) as an efficient oxidizing agent under thermal and sono-thermal conditions has been investigated. In contrast to the thermal reaction, a decrease of the amount of oxidant and an increase of the rate of reaction are observed by simultaneously applying heat and ultrasound. The nature of both C-4 and C-5 substituents on the heterocyclic ring influences the rate of reaction under both conditions. The proposed electron-transfer-induced dehydrogenation in this study is supported by conductometric studies. (C) 2010 Elsevier B.V. All rights reserved.