2,6-diphenyl-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: 2,6-diphenyl-4-(trifluoromethyl)pyrimidine
• 英文别名: 2,4-diphenyl-6-(trifluoromethyl)pyrimidine
• 化学式: C₁₇H₁₁F₃N₂
• 分子量: 300.283
• InChiKey: PQSGFCYBRFYJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  phenylethynyl trifluoromethyl sulfone 在 copper diacetate 、 碳酸氢钠 、 苯甲脒 作用下， 以 乙腈 为溶剂， 反应 36.0h， 生成 2,6-diphenyl-4-(trifluoromethyl)pyrimidine
  参考文献：
  名称：

  Copper-Catalyzed Trifluoromethylalkynylation of Isocyanides

  摘要：

  The title reaction proceeds with acetylenic triflones and isocyanides under mild conditions using copper as a catalyst. This transformation provides an efficient access to (E)-N-alkyl trifluoromethyl alkynyl ketoimines, which are useful building blocks for the synthesis of CF3-containing N-heterocycles, propargylamines, etc.

  DOI：

  10.1021/acs.orglett.5b00730

文献信息

• New approaches to β-trifluoromethylated enone derivatives
  作者：In Howa Jeong、Sung Lan Jeon、Myong Sang Kim、Bum Tae Kim

  DOI：10.1016/j.jfluchem.2004.09.021

  日期：2004.11

  stereospecifically or high stercoselectively in 31–92% yields from the reaction of Weinreb amides with trifluoropropynyl lithium, followed by quenching with H2O in the presence of amine derivatives. β-Trifluoromethylated enaminone 1a was reacted with aryl or alkynyl Grignard reagents to give Michael addition products 5 at 0 °C, whereas addition–elimination adducts, β-aryl (or alkynyl)-β-trifluoromethylated

  从Weinreb酰胺与三氟丙炔基锂反应，然后在胺衍生物存在下，用H 2 O淬灭，以31-92％的产率立体定向或高立体选择性地制备β-三氟甲基化的烯胺酮1。β-三氟甲基化的烯胺酮1a与芳基或炔基格氏试剂在0°C下反应，得到迈克尔加成产物5，而加成-消除加合物β-芳基（或炔基）-β-三氟甲基化的烯酮6在50-在室温下搅拌数小时后，产率为92％。
• Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines
  作者：Alexander Yu. Rulev、Alexey R. Romanov、Alexander V. Popov、Evgeniy V. Kondrashov、Sergey V. Zinchenko

  DOI：10.1055/s-0040-1707969

  日期：2020.5

  one-pot synthesis of trifluoromethylated pyrimidines has been achieved by the treatment of fluorinated 2-bromoenones with aryl- and alkylamidines. The assembly of pyrimidine core proceeds by the cascade reactions via aza-Michael addition–intramolecular cyclization–dehydrohalogenation/dehydration sequence. This strategy is featured by high selectivity and mild reaction conditions giving the target heterocycles

  通过用芳基和烷基am处理氟化的2-溴代烯酮，可以轻松地一锅合成三氟甲基化的嘧啶。嘧啶核的组装是通过aza-Michael加成-分子内环化-脱氢卤化/脱水序列的级联反应进行的。该策略的特点是高选择性和温和的反应条件，可高产率（高达99％）提供目标杂环。证明了三氟甲基对反应路径的独特影响。
• One-pot Preparation of 2,6-Disubstituted 4-(Trifluoromethyl)pyrimidines <i>via</i> the Tandem Cyclization, Dehydration, and Oxidation Reaction of α,β-Unsaturated Trifluoromethyl Ketones Using POCl₃-Pyridine-Silica Gel and MnO₂ Systems
  作者：Kazumasa Funabiki、Hiroko Nakamura、Masaki Matsui、Katsuyoshi Shibata

  DOI：10.1055/s-1999-2741

  日期：1999.6

  The treatment of α,β-unsaturated trifluoromethyl ketones with amidines in acetonitrile gave the corresponding 4-hydroxy-4-(trifluoromethyl)-3,5,6-trihydropyrimidines, followed by successive dehydration with phosphorus oxychloride-pyridine-silica gel and oxidation with manganese(IV) oxide, producing 2,6-disubstituted 4-(trifluoromethyl)pyrimidines in good to excellent yields.

  在乙腈中，以酰胺处理α,β-不饱和三氟甲基酮，得到了相应的4-羟基-4-(三氟甲基)-3,5,6-三氢嘧啶，随后通过磷酰氯-吡啶-硅胶依次脱水，再以二氧化锰氧化，在优良至极佳的产率下生成2,6-二取代4-(三氟甲基)嘧啶。
• 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。
• ETHERIC (ETHEREAL) OXYGEN ATOM-CONTAINING PERFLUOROALKYL GROUP-SUBSTITUTED PYRIMIDINE RING COMPOUND, AND METHOD FOR ITS PRODUCTION
  申请人：ASAHI GLASS COMPANY, LIMITED

  公开号：US20170050934A1

  公开（公告）日：2017-02-23

  To provide a pyrimidine derivative having a fluorinated substituent group, that can be applied to an agricultural chemical or pharmaceutical having excellent pharmacological activities, and a method for producing said derivative. A compound represented by the following formula (A). R f is a group having an etheric (ethereal) oxygen atom inserted between carbon-carbon atoms in a C 2-19 perfluoroalkyl group, wherein the total of the number of carbon atoms and the number of oxygen atoms is from 3 to 20. R 1 is a C 1-6 alkyl group, etc. Q 1 is R 2 C(O)—, R 3 OC(O)—, a carboxy group, R 4 OC(O)NH—, an amino group, or R 5 C(O)NH—(R 2 to R 5 are each independently a C 1-6 alkyl group, etc.).

  提供一种具有氟代取代基的嘧啶衍生物，可应用于具有优异药理活性的农药或药物，并提供一种制备该衍生物的方法。以下是表示的化合物（A）的公式。Rf是一个在C2-19全氟烷基中的碳-碳原子之间插入了醚氧原子的基团，其中碳原子数和氧原子数的总和为3到20。R1是C1-6烷基基团等。Q1是R2C(O)—，R3OC(O)—，一个羧基，R4OC(O)NH—，一个氨基，或R5C(O)NH—（R2到R5分别是独立的C1-6烷基基团等）。