4-(4-溴苯基)-6-(三氟甲基)-2-嘧啶基苯胺 | 327098-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4-(4-溴苯基)-6-(三氟甲基)-2-嘧啶基苯胺
• 英文名称: 4-(4-bromophenyl)-6-trifluoromethyl-2-aminopyrimidine
• 英文别名: 2-amino-4-(4-bromophenyl)-6-(trifluoromethyl)pyrimidine；2-amino-6-(4-bromophenyl)-4-trifluoromethylpyrimidine；4-(4-Bromophenyl)-6-(trifluoromethyl)-2-pyrimidinylamine；4-(4-bromophenyl)-6-(trifluoromethyl)pyrimidin-2-amine
• CAS: 327098-68-0
• 化学式: C₁₁H₇BrF₃N₃
• mdl: MFCD01312150
• 分子量: 318.096
• InChiKey: KJXMTKNZTBVNTC-UHFFFAOYSA-N

物化性质

• 熔点：
  215-218°C
• 沸点：
  442.1±55.0 °C(Predicted)
• 密度：
  1.646±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 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：
  51.8
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2933599090

反应信息

• 作为产物：
  描述：

  5-(4-bromophenyl)-7-trifluoromethyltetrazolo[1,5-a]pyrimidine 在 乙醇 作用下， 以78%的产率得到4-(4-溴苯基)-6-(三氟甲基)-2-嘧啶基苯胺
  参考文献：
  名称：

  Reactivity of trifluoromethyl-tetrazolo[1,5-a]pyrimidines in click chemistry and hydrogenation

  摘要：

  DOI：

  10.1016/j.jfluchem.2022.109973

文献信息

• Synthesis, Fungicidal Activity and Mode of Action of 4-Phenyl-6-trifluoromethyl-2-aminopyrimidines against Botrytis cinerea
  作者：Chunhui Liu、Zining Cui、Xiaojing Yan、Zhiqiu Qi、Mingshan Ji、Xinghai Li

  DOI：10.3390/molecules21070828

  日期：——

  Anilinopyrimidines are the main chemical agents for management of Botrytis cinerea. However, the drug resistance in fungi against this kind of compounds is very serious. To explore new potential fungicides against B. cinerea, a series of 4-phenyl-6-trifluoromethyl-2-amino-pyrimidine compounds (compounds III-1 to III-22) were synthesized, and their structures were confirmed by 1H-NMR, IR and MS. Most of these compounds possessed excellent fungicidal activity. The compounds III-3 and III-13 showed higher fungicidal activity than the positive control pyrimethanil on fructose gelatin agar (FGA), and compound III-3 on potato dextrose agar (PDA) indicated high activity compared to the positive control cyprodinil. In vivo greenhouse results indicated that the activity of compounds III-3, III-8, and III-11 was significantly higher than that of the fungicide pyrimethanil. Scanning electron micrography (SEM) and transmission electron micrography (TEM) were applied to illustrate the mechanism of title compounds against B. cinerea. The title compounds, especially those containing a fluorine atom at the ortho-position on the benzene ring, could maintain the antifungal activity against B. cinerea, but their mechanism of action is different from that of cyprodinil. The present study lays a good foundation for us to find more efficient reagents against B. cinerea.

  苯胺嘧啶类是防治灰葡萄孢的主要化学药剂。然而，真菌对此类化合物的耐药性非常严重。为了探索新的防治灰葡萄孢的潜在杀菌剂，合成了一系列4-苯基-6-三氟甲基-2-氨基嘧啶类化合物(III-1至III-22)，并通过1H-NMR、IR和MS确认了其结构。这些化合物大多具有优异的杀菌活性。化合物III-3和III-13在果糖明胶琼脂(FGA)上的杀菌活性高于阳性对照嘧菌胺，化合物III-3在马铃薯葡萄糖琼脂(PDA)上的活性表明其与阳性对照环丙酰菌胺相比具有高活性。温室试验结果表明，化合物III-3、III-8和III-11的活性显著高于杀菌剂嘧菌胺。通过扫描电子显微镜(SEM)和透射电子显微镜(TEM)说明了这些化合物对灰葡萄孢的作用机制。这些化合物，特别是含有苯环上邻位氟原子的化合物，能够维持对灰葡萄孢的抗真菌活性，但其作用机制与环丙酰菌胺不同。本研究为我们寻找更高效的防治灰葡萄孢的药剂奠定了良好的基础。
• Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds
  作者：Takashi Yamazaki、Yoh Nakajima、Minato Iida、Tomoko Kawasaki-Takasuka

  DOI：10.3762/bjoc.17.14

  日期：——

  The concise preparation of 4,4,4-trifluorobut-2-yn-1-ones by the oxidation of the readily accessible corresponding propargylic alcohols as well as their utilization as Michael acceptors for the construction of aromatic and heteroaromatic compounds are reported.

  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。
• Reactivity of trifluoromethyl-tetrazolo[1,5-a]pyrimidines in click chemistry and hydrogenation
  作者：Elisandra Scapin、Geórgia C. Zimmer、Jean C.B. Vieira、Catarina A.B. Rodrigues、Carlos A.M. Afonso、Nilo Zanatta、Helio G. Bonacorso、Clarissa P. Frizzo、Marcos A.P. Martins

  DOI：10.1016/j.jfluchem.2022.109973

  日期：2022.5