2-trifluoromethyl-N-(1-phenylethylidene)benzenamine | 75040-61-8

• 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: 2-trifluoromethyl-N-(1-phenylethylidene)benzenamine
• 英文别名: N-(1-phenylethylidene)-2-(trifluoromethyl)aniline；N-(1-methylbenzylidene)-2-aminobenzotrifluoride；2-(trifluoromethyl)aniline；1-phenyl-N-[2-(trifluoromethyl)phenyl]ethanimine
• CAS: 75040-61-8
• 化学式: C₁₅H₁₂F₃N
• 分子量: 263.262
• InChiKey: UMBKACIBRAWKON-UHFFFAOYSA-N

物化性质

• 熔点：
  22-25 °C
• 沸点：
  108 °C(Press: 0.14 Torr)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-trifluoromethyl-N-(1-phenylethylidene)benzenamine 在 oxonium 作用下， 以 四氢呋喃 为溶剂， 生成 2-苯基-1H-喹啉-4-酮
  参考文献：
  名称：

  An unusual base-mediated cyclization of ketimines derived from 2-(trifluoromethyl)aniline that involves the trifluoromethyl group: an expedient route to 2-arylquinolines

  摘要：

  DOI：

  10.1021/jo00303a001
• 作为产物：
  描述：

  邻氨基三氟甲苯 在 2,2,6,6-四甲基哌啶 、 dihydrogen threo-(1,2-dibromo-1-phenylpropyl)phosphonate 作用下， 生成 2-trifluoromethyl-N-(1-phenylethylidene)benzenamine
  参考文献：
  名称：

  Monomeric metaphosphate anion: reaction with carbonyl groups

  摘要：

  DOI：

  10.1021/ja00395a030

文献信息

• Chiral phosphine-phosphoramidite ligands for highly enantioselective hydrogenation of N-arylimines
  作者：Qing Li、Chuan-Jin Hou、Xiao-Ning Liu、De-Zhi Huang、Yan-Jun Liu、Rui-Feng Yang、Xiang-Ping Hu

  DOI：10.1039/c4ra16062b

  日期：——

  The asymmetric hydrogenation of N-arylimines with the chiral phosphine-phosphoramidite ligand, (Sc,Sa)-PEAPhos 2b, has been developed. The results revealed that the presence of the substituents on the 3,3′-positions of the binaphthyl backbone significantly improved the enantioselectivity. The utility of this methodology was demonstrated in the synthesis of the chiral fungicide (R)-metalaxyl.

  已经开发了具有手性膦-亚磷酰胺配体（S c，S a）-PEAPhos 2b的N-芳基丙氨酸的不对称氢化。结果表明，在联萘骨架的3，3'-位置上的取代基的存在显着提高了对映选择性。该方法的实用性在手性杀菌剂（R）-甲霜灵的合成中得到了证明。
• [EN] QUINOLINES DERIVATIVES AS NOVEL ANTICANCER AGENTS<br/>[FR] DÉRIVÉS DE QUINOLINES EN TANT QUE NOUVEAUX AGENTS ANTICANCÉREUX
  申请人：GENOSCIENCE PHARMA

  公开号：WO2014147611A8

  公开（公告）日：2014-11-20
• Further studies on the cyclization of aromatic azomethines ortho-substituted with a trifluoromethyl group: synthesis of 2,4-di- or 2,3,4-trisubstituted quinolines
  作者：Lucjan Strekowski、Steven E. Patterson、Lubomir Janda、Roman L. Wydra、Donald B. Harden、Malgorzata Lipowska、Marek T. Cegla

  DOI：10.1021/jo00027a037

  日期：1992.1

  The scope and limitations of the novel synthetic route to quinolines (Strekowski et al. J. Org. Chem. 1990, 55, 4777) have been studied. A direct condensation of 2-(trifluoromethyl)aniline (1) with methyl aryl ketones, methyl heteroaryl ketones, ethyl aryl ketones, methyl vinyl ketones, 1-indanone, 1-tetralone, camphor, and cyclohexanone provides an easy access to the corresponding ketimines. An indirect one-pot preparation of dialkyl ketimines and C-alkyl-substituted amidines derived from 1, but inaccessible by the direct condensation method, is also presented. All these ketimines and amidines are cyclized in the presence of alkylamide, dialkylamide, or alkoxide bases to give a quinoline containing the base function at C-4. Analysis of byproducts of the base-mediated reactions provides strong support for the originally proposed mechanism of the quinoline formation.
• Oxo/imido heterometathesis between N-sulfinylamines and ketones catalyzed by a silica-supported molybdenum imido complex
  作者：Pavel A. Zhizhko、Anton A. Zhizhin、Dmitry N. Zarubin、Nikolai A. Ustynyuk

  DOI：10.1016/j.mencom.2012.03.003

  日期：2012.3

  Grafting the molecular complex (MesN)(2)Mo(CH2CMe2Ph)(2) onto the surface of silica dramatically enhances its catalytic activity in the oxo/irnido heterometathesis reaction of N-sulfinylamines with carbonyl compounds.
• Monomeric methyl metaphosphate: reactions with carbonyl groups
  作者：Arnold C. Satterthwait、F. H. Westheimer

  DOI：10.1021/ja00533a027

  日期：1980.6