ethyl 1,6-dimethyl-2-oxo-4-trifluoromethyl-1,2-dihydropyrimidine-5-carboxylate | 1397257-80-5

• 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 1,6-dimethyl-2-oxo-4-trifluoromethyl-1,2-dihydropyrimidine-5-carboxylate
• 英文别名: Ethyl 1,6-dimethyl-2-oxo-4-(trifluoromethyl)pyrimidine-5-carboxylate
• CAS: 1397257-80-5
• 化学式: C₁₀H₁₁F₃N₂O₃
• 分子量: 264.204
• InChiKey: WRTNZUWKDOYKAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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 1,6-dimethyl-2-oxo-4-trifluoromethyl-1,2-dihydropyrimidine-5-carboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以62%的产率得到ethyl 6-bromomethyl-1-methyl-2-oxo-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
• 作为产物：
  描述：

  N-(methoxycarbonyl)trifluoroacetimidoyl chloride 、 3-(甲基氨基)巴豆酸乙酯 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以55%的产率得到ethyl 1,6-dimethyl-2-oxo-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。
• Hydroaminoalkyl Functionalization of Pyrimidin‐2(1<i>H</i>)‐ones by Visible Light Organophotocatalysis: A Radical Approach to Biginelli‐Type Dihydropyrimidines
  作者：Oleh Lukianov、Viktor Tkachuk、Svitlana Shishkina、Leonid Lachmann、Olga Vadzyuk、Petro Borysko、Dmytro Kovalskyy、Isabelle Gillaizeau、Volodymyr Sukach

  DOI：10.1002/adsc.202300781

  日期：2023.10.24

  visible-light-mediated hydroaminoalkylation of pyrimidin-2(1H)-ones via the aza-Giese-type reaction in presence of acridinium dye as photocatalyst under mild aerobic conditions. Using N-Boc protected aminoalkyl trifluoroborates as radical precursors and various pyrimidine-2(1H)-one substrates, a diverse set of Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones was prepared in 31–73% yields. Further transformation

  在此，我们报道了在吖啶鎓染料作为光催化剂存在下，在温和有氧条件下，通过氮杂吉斯型反应，可见光介导的嘧啶-2(1H)-酮的氢氨烷基化。使用N -Boc 保护的氨基烷基三氟硼酸盐作为自由基前体和各种嘧啶-2(1 H )-酮底物，以 31-73% 的浓度制备了多种 Biginelli 型 3,4-二氢嘧啶-2(1 H )-酮产量。所得产物的进一步转化使得能够合成3,6,7,7a-四氢-1H-吡咯并[3,4-d]嘧啶-2,5-二酮衍生物，该衍生物有望作为聚（ADP-核糖）抑制剂) 聚合酶 (PARP)（荧光测定中 PARP-2 的 IC50 为 0.46–1.12 μM）。