5-tert-butyl-6-chloro-N-[(4-(trifluoromethyl)phenyl)]pyrazine-2-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-tert-butyl-6-chloro-N-[(4-(trifluoromethyl)phenyl)]pyrazine-2-carboxamide
• 英文别名: 5-tert-butyl-6-chloro-N-[4-(trifluoromethyl)phenyl]pyrazine-2-carboxamide；5-tert-butyl-6-chloro-N-(4-trifluoromethylphenyl)-pyrazine-2-carboxamide；5-tert-butyl-6-chloro-N-(4-trifluoromethylphenyl)pyrazine-2-carboxamide
• 化学式: C₁₆H₁₅ClF₃N₃O
• 分子量: 357.763
• InChiKey: YGAYLVGAIOIANM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对三氟甲基苯胺 、 6-chloro-5-tert-butylpyrazine-2-carboxylic acid chloride 在 吡啶 作用下， 以 丙酮 为溶剂， 生成 5-tert-butyl-6-chloro-N-[(4-(trifluoromethyl)phenyl)]pyrazine-2-carboxamide
  参考文献：
  名称：

  取代的 N-苯基吡嗪-2-甲酰胺：合成和抗分枝杆菌评价

  摘要：

  取代的吡嗪羧酸的氯化物与环取代的苯胺缩合产生十二个取代的吡嗪羧酸酰胺。介绍了新合成化合物的合成方法、分析和亲脂性数据。使用了两种抗结核试验。首先，研究了一系列吡嗪衍生物对四种不同分枝杆菌菌株的抗分枝杆菌活性。其次，抗分枝杆菌评估是在结核病抗微生物采集和协调机构 (TAACF) 计划中进行的。发现了有趣的体外抗分枝杆菌活性，N-(3-iodo-4-methyl-phenyl)pyrazine-2-carboxamide (9) 是对结核分枝杆菌最有效的衍生化合物（MIC < 2.0 μmol/L），

  DOI：

  10.3390/molecules14104180

文献信息

• Substituted N-Phenylpyrazine-2-carboxamides, Their Synthesis and Evaluation as Herbicides and Abiotic Elicitors
  作者：Martin Doležal、Lenka Tůmová、Diana Kešetovičová、Jiří Tůma、Katarína Kráľová

  DOI：10.3390/12122589

  日期：——

  The condensation of substituted pyrazine-2-carboxylic acid chlorides with ring-substituted anilines yielded five substituted pyrazine-2-carboxylic acid amides. Thesynthesis, and analytical, lipophilicity and biological data of the newly synthesizedcompounds are presented in this paper. The photosynthesis inhibition, antialgal activityand the effect of a series of pyrazine derivatives as abiotic elicitors

  取代的吡嗪-2-羧酸氯化物与环取代的苯胺缩合产生五个取代的吡嗪-2-羧酸酰胺。本文介绍了新合成化合物的合成、分析、亲脂性和生物学数据。研究了光合作用抑制、抗藻活性和一系列吡嗪衍生物作为非生物诱导剂对 Ononis arvensis (L.) 愈伤组织培养物中黄酮类化合物积累的影响。菠菜叶绿体中析氧速率最活跃的抑制剂是 6-氯-吡嗪-2-羧酸（3-碘-4-甲基苯基）-酰胺（2，IC(50) = 51.0 μmol.L(-1)） . 发现 5-叔丁基-N-(4-氯-3-甲基苯基)-吡嗪-2-甲酰胺 (3, IC(50) = 44.0 micromol. L(-1))。在使用 6-氯吡嗪-2-羧酸（3-碘-4-甲基苯基）-酰胺 (2) 进行 12 小时的诱导过程后，达到了最大的类黄酮产量（约 900%）。
• Spectroscopic (FT-IR, FT-Raman), first order hyperpolarizability, NBO analysis, HOMO and LUMO analysis of 5-tert-Butyl-6-chloro-N-[(4-(trifluoromethyl)phenyl]pyrazine-2-carboxamide
  作者：J.B. Bhagyasree、Hema Tresa Varghese、C. Yohannan Panicker、Christian Van Alsenoy、Abdulaziz A. Al-Saadi、Martin Dolezal、Jadu Samuel

  DOI：10.1016/j.saa.2014.08.104

  日期：2015.2

  The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-tert-Butyl-6-chloro-N-[(4-(trifluoromethyl)phenyl]Pyrazine-2-carboxamide have been investigated experimentally and theoretically using Gaussian09 software package. Potential energy distribution of normal modes of vibrations was done using GAR2PED program. The HOMO and LUMO analysis is used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. From the NBO analysis it is evident that the increased electron density at the nitrogen, carbon atoms leads to the elongation of respective bond length and a lowering of the corresponding stretching wave number. The calculated geometrical parameters are in agreement with that of similar derivatives. The calculated first hyperpolarizability is high and the calculated data suggest an extended sr-electron delocalization over the pyrazine ring and carboxamide moiety which is responsible for the nonlinearity of the molecule. (c) 2014 Elsevier B.V. All rights reserved.