4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide

• 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: 4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: 4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxamide
• 化学式: C₁₈H₁₆FN₃O₂
• 分子量: 325.342
• InChiKey: JSSOFNWHAXUUGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide 、 苯甲醛 在 iron(III) chloride hexahydrate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以84%的产率得到(E)-4-(4-fluorophenyl)-2-oxo-N-phenyl-6-styryl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  铁催化的比格内利产物的乙烯基醛醇缩合反应及其在吡喃并[4,3- d ]嘧啶酮中的应用

  摘要：

  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。

  DOI：

  10.1021/jo402773r
• 作为产物：
  描述：

  4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carbothioamide 在 溶剂黄146 、 sodium nitrite 作用下， 反应 8.0h， 以41%的产率得到4-(4-fluorophenyl)-6-methyl-2-oxo-N-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  2-Acylthioacetamides in the Biginelli Reaction

  摘要：

  We have demonstrated for the first time a Biginelli reaction of 2-acylthioacetamides with aromatic aldehydes and ureas or thioureas, leading to N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydro-pyrimidine-5-carbothioamides. The regioselectivity of this process matched the concept of hard/soft Lewis acids and bases. It was established that nitrous acid or other oxidants converted the synthesized compounds into N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxamides, and not the expected 4-Ar-2-6-R-1-1-R-2-5-(1,3-benzothiazol-2-yl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).

  DOI：

  10.1007/s10593-014-1429-z

文献信息

• 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。
• Iron-catalyzed four-member multicomponent reaction for assembly of (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Zhiguo Zhang、Lianqiang Zhang、Xinyu Duan、Xiangqian Yan、Yan Yan、Qingfeng Liu、Tongxin Liu、Guisheng Zhang

  DOI：10.1016/j.tet.2015.07.039

  日期：2015.10

  A novel iron-catalyzed one-pot multi-component tandem reaction of acetoacetamide, urea, and two molecules of aryl aldehydes has been developed. This reaction provides a general, straightforward, practical and useful method for the preparation of potential bioactive (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones. They are also versatile precursors leading to diverse drug-like dihydropyrimidin-2(1H)-one

  已开发出一种新的铁催化的乙酰乙酰胺，尿素和两分子芳基醛的单锅多组分串联反应。该反应为制备潜在的生物活性（E）-6-芳基乙烯基-3,4-二氢嘧啶-2（1 H）-酮提供了一种通用，直接，实用和有用的方法。它们还是通用的前体，可产生多种药物样的二氢嘧啶-2（1 H）-一衍生物。避免质子酸并使用单一廉价且对环境无害的催化剂的特征使该方法更有价值。
• 2-Acylthioacetamides in the Biginelli Reaction
  作者：M. N. Kurmach、A. B. Ryabitskiy、V. N. Britsun

  DOI：10.1007/s10593-014-1429-z

  日期：2014.3

  We have demonstrated for the first time a Biginelli reaction of 2-acylthioacetamides with aromatic aldehydes and ureas or thioureas, leading to N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydro-pyrimidine-5-carbothioamides. The regioselectivity of this process matched the concept of hard/soft Lewis acids and bases. It was established that nitrous acid or other oxidants converted the synthesized compounds into N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxamides, and not the expected 4-Ar-2-6-R-1-1-R-2-5-(1,3-benzothiazol-2-yl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).