ethyl 1-methyl-2-oxo-6-phenyl-4-trifluoromethyl-1,2-dihydropyrimidine-5-carboxylate | 1397258-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl 1-methyl-2-oxo-6-phenyl-4-trifluoromethyl-1,2-dihydropyrimidine-5-carboxylate
• 英文别名: Ethyl 1-methyl-2-oxo-6-phenyl-4-(trifluoromethyl)pyrimidine-5-carboxylate；ethyl 1-methyl-2-oxo-6-phenyl-4-(trifluoromethyl)pyrimidine-5-carboxylate
• CAS: 1397258-04-6
• 化学式: C₁₅H₁₃F₃N₂O₃
• 分子量: 326.275
• InChiKey: IWKGWGCMPASZMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 1-methyl-2-oxo-6-phenyl-4-trifluoromethyl-1,2-dihydropyrimidine-5-carboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以41%的产率得到ethyl 3-methyl-2-oxo-4-phenyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Heterocyclization of N-(1-chloro-2,2,2-trifluoroethylidene)carbamates with β-enaminoesters—a novel synthetic strategy to functionalized trifluoromethylated pyrimidines

  摘要：

  A novel synthetic strategy to 4-trifluoromethyl substituted 2-oxo-1,2-dihydropyrimidine-5-carboxylates has been developed based on the cyclocondensation of beta-enaminoesters with N-(1-chloro-2,2,2trifluoroethylidene)carbamates. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.099
• 作为产物：
  描述：

  ethyl 3-(methylamino)-3-phenylacrylate 、 N-benzyloxycarbonyl-2,2,2-trifluoroacetimidoyl chloride 在 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以40%的产率得到ethyl 1-methyl-2-oxo-6-phenyl-4-trifluoromethyl-1,2-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Heterocyclization of N-(1-chloro-2,2,2-trifluoroethylidene)carbamates with β-enaminoesters—a novel synthetic strategy to functionalized trifluoromethylated pyrimidines

  摘要：

  A novel synthetic strategy to 4-trifluoromethyl substituted 2-oxo-1,2-dihydropyrimidine-5-carboxylates has been developed based on the cyclocondensation of beta-enaminoesters with N-(1-chloro-2,2,2trifluoroethylidene)carbamates. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.099

文献信息

• Control of Regio- and Enantioselectivity in the Asymmetric Organocatalytic Addition of Acetone to 4-(Trifluoromethyl)pyrimidin-2(1<i>H</i>)-ones
  作者：Volodymyr A. Sukach、Viktor M. Tkachuk、Veronika M. Shoba、Volodymyr V. Pirozhenko、Eduard B. Rusanov、Alexey A. Chekotilo、Gerd-Volker Röschenthaler、Mykhailo V. Vovk

  DOI：10.1002/ejoc.201301542

  日期：2014.3

  The reactions of variously substituted 4-(trifluoromethyl)pyrimidin-2(1H)-ones with acetone in the presence of L-proline or chiral secondary amine organocatalysts were studied. As demonstrated, 4-(trifluoromethyl)pyrimidin-2(1H)-ones unsubstituted at the 6-position of the heterocyclic ring react with acetone at the endocyclic C=N or C=C bond depending on whether thermodynamic or kinetic control is

  研究了不同取代的 4-(三氟甲基)嘧啶-2(1H)-酮与丙酮在 L-脯氨酸或手性仲胺有机催化剂存在下的反应。正如所证明的，在杂环的 6-位未取代的 4-(三氟甲基)嘧啶-2(1H)-ones 与丙酮在环内 C=N 或 C=C 键上反应，这取决于热力学或动力学控制是否有效加成反应也取决于所用的催化剂。外消旋动力学优选的区域异构体，6-(2-氧代丙基)-4-(三氟甲基)-3,4-二氢嘧啶-2(1H)-ones，被发现经历分子间有机催化重排成对映​​体富集的热力学稳定产物，4-(2- oxopropyl)-4-(trifluoromethyl)-3,4-dihydropyrimidin-2(1H)-ones，对映体比例高达 83:17。
• Development of an efficient route to CF₃-substituted pyrrolopyrimidines through understanding the competition between Michael and aza-Henry reactions
  作者：V. M. Tkachuk、V. A. Sukach、K. V. Kovalchuk、M. V. Vovk、V. G. Nenajdenko

  DOI：10.1039/c4ob02233e

  日期：——

  A simple control of temperature and time in the nitromethane addition to 4-trifluoromethylated pyrimidin-2-ones allowed regioselective synthesis of isomeric products.

  通过对硝基甲烷加入4-三氟甲基嘧啶-2-酮的温度和时间进行简单控制，实现了同分异构体产物的区域选择性合成。
• Heterocyclization of N-(1-chloro-2,2,2-trifluoroethylidene)carbamates with β-enaminoesters—a novel synthetic strategy to functionalized trifluoromethylated pyrimidines
  作者：Volodymyr A. Sukach、Viktor M. Tkachuk、Eduard B. Rusanov、Gerd-Volker Röschenthaler、Mykhaylo V. Vovk

  DOI：10.1016/j.tet.2012.07.099

  日期：2012.10

  A novel synthetic strategy to 4-trifluoromethyl substituted 2-oxo-1,2-dihydropyrimidine-5-carboxylates has been developed based on the cyclocondensation of beta-enaminoesters with N-(1-chloro-2,2,2trifluoroethylidene)carbamates. (c) 2012 Elsevier Ltd. All rights reserved.