2-Phenyl-3-(trifluoromethyl)quinoxaline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-Phenyl-3-(trifluoromethyl)quinoxaline
• 英文别名: 2-Trifluoromethyl-3-phenylquinoxaline；2-phenyl-3-trifluoromethylquinoxaline；3-trifluoromethyl-2-phenylquinoxaline；2-trifluoromethyl-3-phenylquinxoaline
• 化学式: C₁₅H₉F₃N₂
• 分子量: 274.245
• InChiKey: GBUYGLUNANSKLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  iridium(III) chloride trihydrate 、 2-Phenyl-3-(trifluoromethyl)quinoxaline 在 N,N-二异丙基乙胺 作用下， 以 二乙二醇二甲醚 、 水 为溶剂， 以159 mg的产率得到
  参考文献：
  名称：

  JP2022017658A

  摘要：

  公开号：
• 作为产物：
  描述：

  2-羟基-3-三氟甲基喹噁啉 在 palladium diacetate 、 三溴化磷 、 sodium carbonate 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.0h， 生成 2-Phenyl-3-(trifluoromethyl)quinoxaline
  参考文献：
  名称：

  由3-（三氟甲基）喹喔啉-2（1 H）-一和3-（三（二）氟甲基）喹喔啉-2-羧酸合成新的2-取代的3-（三（二）氟甲基）-喹喔啉

  摘要：

  从3-（三氟甲基）喹喔啉-2（1 H）-1开始，获得了许多新的2-取代的3-（三氟甲基）喹喔啉，包括氨基，溴，氯，肼基，苯基，α-呋喃基，甲酰基。 ，甲硫基和甲磺酰基衍生物。首次获得3-（三（二）-氟甲基）喹喔啉-2-羧酸，用于合成2-氨基-3-（三（二）-氟甲基）喹喔啉和2-（2-氨基噻唑） -4-基）-3-（三氟甲基）喹喔啉。

  DOI：

  10.1007/s10593-015-1694-5

文献信息

• A facile synthesis of fluorine-containing heterocycles - use of 1,1,1-trifluoro-2-alkanones as a convenient synthetic intermediate
  作者：Yasuhiro Kamitori

  DOI：10.1002/jhet.5570380339

  日期：2001.5

  3-alkanediones 2 easily obtainable from various aldehyde dialkylhydrazones were reacted with several diamines to afford trifluoromethylquinoxalines 3 and trifluoromethylpyrazines 4 in good yields. With the use of aldehydes and aqueous ammonia instead of diamines, diketones 2 were successfully converted to the corresponding 4-trifluoromethylimidazoles 5 in satisfactory yields.

  容易从各种醛二烷基hydr得到的1,1,1-三氟-2,3-烷二酮2与几种二胺反应，以高收率得到三氟甲基喹喔啉3和三氟甲基吡嗪4。通过使用醛和氨水代替二胺，二酮2以令人满意的产率成功转化为相应的4-三氟甲基咪唑5。
• Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted aldehydes and ketones with aryl diamines leading to quinoxalines using molecular oxygen as oxidant
  作者：Chun Zhang、Zejun Xu、Liangren Zhang、Ning Jiao

  DOI：10.1016/j.tet.2012.03.020

  日期：2012.7

  A novel Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted carbonyl compounds with aryl diamines leading to quinoxaline derivatives using molecular oxygen as oxidant has been developed. Six hydrogen dissociations involving 2 sp3 C–H bonds activation are realized under mild conditions in this approach. Plausible mechanism is proposed for this novel Et3N-catalyzed transformation on

  已经开发出新颖的Et 3 N催化的α-未取代的羰基化合物与芳基二胺的氧化脱氢偶联，从而使用分子氧作为氧化剂生成喹喔啉衍生物。该方法在温和条件下实现了涉及2个sp 3 C–H键活化的六个氢离解。在经过精心设计的机理研究（包括通过EPR进行自由基检测）的基础上，提出了这种新颖的Et 3 N催化转化的合理机理。© 2012爱思唯尔科学。版权所有。
• Pyrrolo[1,2-<i>a</i>]quinoxalines: Novel Synthesis via Annulation of 2-Alkylquinoxalines
  作者：Sven Ammermann、Christian Hrib、Peter G. Jones、Wolf-Walther du Mont、Wolfgang Kowalsky、Hans-Hermann Johannes

  DOI：10.1021/ol302348v

  日期：2012.10.5

  In an attempt to synthesize a novel homoleptic complex 3 from 2-methyl-3-phenylquinoxaline 1 and Ir(acac)(3) for application as a triplet emitter in OLEDs (organic light-emitting diodes) no cyclometalation was observed. Instead, an annulation to 1-methyl-4-phenylpyrrolo[1,2-a]quinoxaline 2 was observed. Since pyrroloquinoxalines are potentially bioactive and few paths for their synthesis are known, selected reactions and conditions were investigated, suggesting Ir(acac)(3) as catalyst and proving glycerol to be a reactant.
• Trifluoroacetimidoyl lithium; generation and reaction with electrophiles
  作者：Hisayuki Watanabe、Fumio Yamashita、Kenji Uneyama

  DOI：10.1016/s0040-4039(00)91969-5

  日期：1993.3

  N-Aryl trifluoroacetimidoyl lithiums. synthetic equivalent of trifluoroacetyl carbanion, are prepared from N-aryl trifluoroacetimidoyl iodides by iodine-lithium exchange reaction with n-BuLi in ether at -78-degrees-C and react with various electrophiles, leading to synthetic blocks for trifluoromethylated nitrogen heterocycles.
• (Trifluoroacetimidoyl)lithiums and Their Reaction with Electrophiles
  作者：Hisayuki Watanabe、Fengyang Yan、Takashi Sakai、Kenji Uneyama

  DOI：10.1021/jo00083a016

  日期：1994.2

  N-Aryltrifluoroacetimidoyl iodides have been lithiated with n-butyllithium in ether. Because of the highly ionic nature of a carbon-lithium bond, the imidoyl carbanions are only stable below -60 degrees C. The reaction temperature, solvent, and steric bulkiness of the N-aryl substituents greatly affected alkylation. [N-(2,6-dimethylphenyl)trifluoroacetimidoyl] lithium in ether is stable enough to be alkylated and silylated on the imino carbon with electrophiles such as acyl chlorides, aldehydes, ketones, chloroformate, and trimethylsilyl chloride.