1,3-dimethyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione | 188616-75-3

• 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: 1,3-dimethyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 6-trifluoromethyl-1,3-dimethyluracil；3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydro pyrimidine；1,3-dimethyl-6-(trifluoromethyl)uracil；1,3-dimethyl-6-(trifluoromethyl)pyrimidine-2,4-dione
• CAS: 188616-75-3
• 化学式: C₇H₇F₃N₂O₂
• 分子量: 208.14
• InChiKey: NPJVLHHOGCGSIG-UHFFFAOYSA-N

物化性质

• 沸点：
  176.5±50.0 °C(Predicted)
• 密度：
  1.426±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione 在 盐酸 、 N-碘代丁二酰亚胺 、 三甲基氯硅烷 、 1,2-二溴乙烷 、 三氟乙酸 、 三氟乙酸酐 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基乙酰胺 为溶剂， 反应 35.0h， 生成
  参考文献：
  名称：

  Identification of N-acyl 4-(5-pyrimidine-2,4-dionyl)phenylalanine derivatives and their orally active prodrug esters as dual-acting alpha4–beta1 and alpha4–beta7 receptor antagonists

  摘要：

  N-Acyl 4-(5-pyrimidine-2,4-dionyl)phenylalanine derivatives of type 4 were designed to replace the 2,6-dichlorobenzoylamine portion of compound 1 in order to identify novel compounds with improved potency against alpha 4-integrins. Several derivatives were identified as very potent dual-acting alpha 4-integrin, alpha 4 beta 1 and alpha 4 beta 7 antagonists. Investigation of a limited number of prodrug esters led to the discovery of the ethyl ester prodrug 42, which demonstrated good intestinal fluid stability and good permeability. Despite low solubility, 42 gave acceptable blood levels of 30 when dosed orally in non-human primates. Additionally, 42 had an overall excellent profile and was selected for clinical trials. Investigation of N-acyl 4-(5-pyrimidine-2,4-dionyl)phenylalanine derivatives led to the discovery of several very potent dual-acting alpha 4-integrin antagonists. Ethyl ester prodrug 42 advanced to human clinical trials based on the excellent intestinal fluid stability, good permeability and superior efficacy in non-human primates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.026
• 作为产物：
  描述：

  1,3-二甲基-5-(三氟甲基)嘧啶-2,4-二酮 在 copper(l) iodide 、 2,6-二叔丁基吡啶 、 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 、 caesium carbonate 、 联硼酸频那醇酯 、 三(五氟苯基)膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.0h， 生成 1,3-dimethyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  C-H Trifluoromethylations of 1,3-Dimethyluracil and Reactivity of the Products in C-H Arylations

  摘要：

  Diverse electrophilic, nucleophilic and radical C-H trifluoromethylations of 1,3-dimethyluracil were systematically studied in order to prepare either 5- or 6-(trifluoromethyl)uracil derivatives. Electrophilic reagents led only to dimeric bis-uracil products, whereas the radical trifluoromethylation by CF3SO2Na in presence of t-BuOOH gave 1,3-dimethyl-5-(trifluoromethyl)uracil (2) in good yield. The 6-(trifluoromethyl)uracil derivative 3 was only prepared in low yield and in a mixture with 2 by Ir-catalyzed borylation followed by treatment with the Togni's reagent. Attempted Pd-catalyzed C-H arylations of 2 in the presence of Cs2CO3 gave mixtures of de-trifluoromethylated products, whereas the reaction with 4-iodotoluene in the presence of CsF gave the desired 6-aryl-5-trifluoromethyluracil derivative 8 in moderate yield and the reaction was not general for other aryl halides.

  DOI：

  10.3987/com-14-12958

文献信息

• 4-Pyrimidinyl-n-acyl-l phenylalanines
  申请人：Hoffmann-La Roche Inc.

  公开号：US06380387B1

  公开（公告）日：2002-04-30

  Compounds of Formula I are disclosed, having activity as inhibitors of binding between VCAM-1 and cells expressing VLA-4, and accordingly useful for treating diseases whose symptoms and or damage are related to the binding of VCAM-1 to cells expressing VLA-4.

  公式I的化合物被披露，具有作为VCAM-1和表达VLA-4的细胞之间结合抑制剂的活性，因此可用于治疗症状和/或损害与VCAM-1与表达VLA-4的细胞结合相关的疾病。
• [EN] ISOXAZOLINE DERIVATIVES AND THEIR USES IN AGRICULTURE RELATED APPLICATION<br/>[FR] DÉRIVÉS D'ISOXAZOLINE ET LEURS UTILISATIONS DANS UNE APPLICATION LIÉE À L'AGRICULTURE
  申请人：DONGGUAN HEC TECH R & D CO LTD

  公开号：WO2019062802A1

  公开（公告）日：2019-04-04

  The present invention provides isoxazoline derivatives and uses thereof in agriculture; in particular, the present invention provides a compound having formula (I), or a stereoisomer, an N-oxide or a salt thereof, preparation methods thereof, and compositions containing these compounds and uses thereof in agriculture, particularly uses as herbicide active ingredients for controlling unwanted plants; wherein R1, R2, R3, R4, n, R5, R6 and Hy are as described in the invention.

  本发明提供了异噁唑啉衍生物及其在农业中的用途；具体而言，本发明提供了具有化学式（I）的化合物，或其立体异构体、N-氧化物或盐，其制备方法，以及含有这些化合物的组合物及其在农业中的用途，特别是作为除草剂活性成分用于控制不受欢迎的植物；其中R1、R2、R3、R4、n、R5、R6和Hy如本发明所述。
• Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived “Ligandless” CuCF₃
  作者：Jordi Mestre、Anton Lishchynskyi、Sergio Castillón、Omar Boutureira

  DOI：10.1021/acs.joc.8b00927

  日期：2018.8.3

  We herein present a flexible approach for the incorporation of CF3 units into a predefined site of electron-rich alkenes that exploits the regiocontrolled introduction of an iodine handle and subsequent trifluoromethylation of the C(sp2)–I bond using fluoroform-derived “ligandless” CuCF3. The broad substrate scope and functional group tolerance together with the scalability and purity of the resulting

  我们在此提出了一种将CF 3单元并入富含电子的烯烃的预定位点的灵活方法，该方法利用了碘控制的区域控制性引入以及随后使用氟仿衍生的“无配位体”对C（sp 2）-I键进行了三氟甲基化。” CuCF 3。广泛的底物范围和官能团耐受性以及所得产品的可扩展性和纯度使复杂的CF 3支架（如糖，核苷（抗病毒剂）和杂环（吲哚和色酮），具有学术和工业应用潜力。
• [EN] BENZOXAZINONE DERIVATIVES USEFUL AS HERBICIDES<br/>[FR] DÉRIVÉS DE BENZOXAZINONE UTILES EN TANT QU'HERBICIDES
  申请人：REDAG CROP PROT LTD

  公开号：WO2019020987A1

  公开（公告）日：2019-01-31

  The present invention relates to compounds which are of use in the field of agriculture as herbicides. The compounds in question are of formula II and comprise a spirofused tricycle core: wherein R4 and R5 together with the carbon atom to which they are attached form a cyclic group.

  本发明涉及一种在农业领域作为除草剂使用的化合物。所涉及的化合物属于公式II，并包括一个螺合三环核心：其中R4和R5与它们附着的碳原子一起形成一个环状基团。
• Convenient preparation of trifluoroacetyl Meldrum’s acid and its use as a building block for trifluoromethyl-containing compounds
  作者：Yasuo Morita、Rika Kamakura、Masaki Takeda、Yutaka Yamamoto

  DOI：10.1039/a608104e

  日期：——

  Trifluoroacetyl Meldrum’s acid is conveniently prepared and applied to the synthesis of trifluoromethyl-containing compounds.

  三氟乙酰梅氏酸的制备非常方便，可用于合成含三氟甲基的化合物。