6-phenyl-4-(trifluoromethyl)pyrimidine

• 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: 6-phenyl-4-(trifluoromethyl)pyrimidine
• 英文别名: 4-phenyl-6-(trifluoromethyl)pyrimidine；4-Phenyl-6-(trifluoromethyl)pyrimidine
• 化学式: C₁₁H₇F₃N₂
• mdl: MFCD18418176
• 分子量: 224.185
• InChiKey: QPHOPRNDAKMBDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-phenyl-4-(trifluoromethyl)pyrimidine 在 N-碘代丁二酰亚胺 、 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以53%的产率得到4-(2-iodophenyl)-6-(trifluoromethyl)pyrimidine
  参考文献：
  名称：

  Pyrimidine as an Aryl C–H Activating Group

  摘要：

  The Pd-catalyzed regioselective C-H activation/arylation, /iodination, and/acetoxylation reactions of 4-arylpyrimidines using aryl iodides, N-iodosuccinimide, and (diacetoxyiodo)benzene respectively as coupling partners are described. Suzuki-Miyaura coupling and Sonogashira reactions of the resulting aryl iodides are demonstrated. The scalability of the C-H activation/functionalization starting with readily accessible 4-aryl pyrimidines is also reported.

  DOI：

  10.1021/acs.orglett.8b01300
• 作为产物：
  描述：

  1-phenyl-4,4,4-trifluorobut-2-yn-1-ol 在 manganese(IV) oxide 、 sodium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.0h， 生成 6-phenyl-4-(trifluoromethyl)pyrimidine
  参考文献：
  名称：

  4,4,4-三氟丁-2-yn-1-酮的简便制备和转化为芳香族和杂芳香族化合物

  摘要：

  报道了通过氧化容易获得的相应炔丙醇来简明制备 4,4,4-三氟丁-2-yn-1-酮，以及它们作为迈克尔受体用于构建芳香族和杂芳香族化合物的用途。

  DOI：

  10.3762/bjoc.17.14

文献信息

• Borazine‐CF ₃ ⁻ Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation
  作者：Jacob B. Geri、Michael M. Wade Wolfe、Nathaniel K. Szymczak

  DOI：10.1002/anie.201711316

  日期：2018.1.26

  A fluoroform‐derived borazine CF3− transfer reagent is used to effect rapid nucleophilic reactions in the absence of additives, within minutes at 25 °C. Inorganic electrophiles spanning seven groups of the periodic table can be trifluoromethylated in high yield, including transition metals used for catalytic trifluoromethylation. Organic electrophiles included (hetero)arenes, enabling C−H and C−X

  甲三氟甲烷衍生的环硼氮烷CF 3 -转移试剂在25用来快速作用的亲核反应在不存在添加剂时，在几分钟内℃。可以高产率地将跨越周期表的七个基团的无机亲电试剂三氟甲基化，包括用于催化三氟甲基化的过渡金属。有机亲电试剂包括（杂）芳烃，可实现CH和CX三氟甲基化反应。机理分析支持CF解离机构3 -转移，和阳离子改性，得到具有增强的稳定性的试剂。
• One-Pot, Atom and Step Economy (PASE) Assembly of Trifluoromethylated Pyrimidines from CF₃ -Ynones
  作者：Alexey R. Romanov、Alexander Yu. Rulev、Igor A. Ushakov、Vasiliy M. Muzalevskiy、Valentine G. Nenajdenko

  DOI：10.1002/ejoc.201700727

  日期：2017.8.2

  Highly efficient synthesis of 6-trifluoromethylated pyrimidines based on reaction of CF3-ynones with nitrogen 1,3-binucleophiles was developed. One-pot assembly of pyrimidine core proceeds by the cascade route via aza-Michael addition - intramolecular cyclization - dehydration sequence giving the target heterocycles in excellent yields (up to 97%). When acetamidine was used as a binucleophile, the

  开发了基于CF3-炔酮与1,3-双亲核试剂氮反应的6-三氟甲基化嘧啶的高效合成方法。嘧啶核的一锅组装通过aza-Michael加成的级联途径进行-分子内环化-脱水序列以优异的收率（最高97％）得到目标杂环。当将乙am用作双亲核试剂时，观察到意想不到的向乙two中添加了两当量的CF3-炔酮。
• Reductive Cleavage of C(sp²)–CF₃ Bonds in Trifluoromethylpyridines
  作者：Piers St. Onge、Shajia I. Khan、Adam Cook、Stephen G. Newman

  DOI：10.1021/acs.orglett.3c00258

  日期：2023.2.17

  of an earth-abundant alkoxide base and silicon hydride species. A variety of pyridine and quinoline substrates bearing alkyl, aryl, and amino functional groups are reduced in moderate to high yields. The reaction is chemoselective for C(sp2)–CF3 groups located at the 2-position on the pyridine ring, leaving trifluoromethyl groups located elsewhere on the molecule intact. Preliminary mechanistic studies

  利用地球上丰富的醇盐碱和氢化硅物种开发了还原性脱三氟甲基化方案。各种带有烷基、芳基和氨基官能团的吡啶和喹啉底物以中等到高产率被还原。该反应对位于吡啶环 2 位的C(sp 2 )–CF 3基团具有化学选择性，使位于分子其他位置的三氟甲基完好无损。初步的机理研究表明，硅烷和碱的结合产生了一个强还原系统，可以将电子转移到缺电子的 π 系统。
• Fluorinated β-Diketo Phosphorus Ylides: Their Cyclocondensation with Amidines Affording 4-Trifluoromethyl- and 4-Perfluoroalkyl-Substituted Pyrimidines
  作者：Masami Kawase、Ryosuke Saijo、Genki Watanabe、Ken-ichi Kurihara

  DOI：10.3987/com-14-13075

  日期：——

  A study is presented for the syntheses of a series of 4-trifluoromethyl-and 4-perfluoroalkyl-substituted pyrimidines from the reaction of trifiuoromethyl or perfluoroalkyl beta-diketo phosphorus ylides (Ph3P=C(CORF)COR) with amidine hydrochloride.
• Pyrimidine as an Aryl C–H Activating Group
  作者：Sahaj Gupta、Jennifer A. Melanson、Louis Vaillancourt、William A. Nugent、Gerald J. Tanoury、Gabriele Schatte、Victor Snieckus

  DOI：10.1021/acs.orglett.8b01300

  日期：2018.7.6

  The Pd-catalyzed regioselective C-H activation/arylation, /iodination, and/acetoxylation reactions of 4-arylpyrimidines using aryl iodides, N-iodosuccinimide, and (diacetoxyiodo)benzene respectively as coupling partners are described. Suzuki-Miyaura coupling and Sonogashira reactions of the resulting aryl iodides are demonstrated. The scalability of the C-H activation/functionalization starting with readily accessible 4-aryl pyrimidines is also reported.