α,α,α-trifluoro-N-phenyl-m-acetotoluidide | 844-04-2

• 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: α,α,α-trifluoro-N-phenyl-m-acetotoluidide
• 英文别名: N-Acetyl-3-trifluormethyl-diphenylamin；N-phenyl-N-(3-trifluoromethyl-phenyl)-acetamide；N-Phenyl-N-(3-trifluormethyl-phenyl)-acetamid；ACETAMIDE, N-PHENYL-N-(alpha,alpha,alpha-TRIFLUORO-m-TOLYL)-；N-phenyl-N-[3-(trifluoromethyl)phenyl]acetamide
• CAS: 844-04-2
• 化学式: C₁₅H₁₂F₃NO
• 分子量: 279.262
• InChiKey: AIEQQLHWKYTELX-UHFFFAOYSA-N

物化性质

• 沸点：
  125-127 °C(Press: 0.5 Torr)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 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：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α,α,α-trifluoro-N-phenyl-m-acetotoluidide 在 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以115.6 mg的产率得到间三氟甲基二苯胺
  参考文献：
  名称：

  铁盐催化合成二芳基胺。

  摘要：

  DOI：

  10.1002/chem.200802018
• 作为产物：
  描述：

  3-(trifluoromethyl)phenyllithium 在 硼酸三甲酯 、 copper diacetate 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 α,α,α-trifluoro-N-phenyl-m-acetotoluidide
  参考文献：
  名称：

  Cupric acetate mediated N-arylation by arylboronic acids: A preliminary investigation into the scope of application

  摘要：

  A range of NH substrates of varying nucleophilicity were reacted with a selection of electronically diverse aryl boronic acids in the presence of cupric acetate in order to evaluate the generality of a previously described N-arylation procedure. The results of that investigation are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01735-3

文献信息

• Fischer Indolization of Ethyl Pyruvate 2-(2-(Trifluoromethyl)phenyl)-phenylhydrazone and New Insight into the Mechanism of the Goldberg Reaction. (Fischer Indolization and Its Related Compounds. XXVI)
  作者：Yasuoki MURAKAMI、Toshiko WATANABE、Takao HAGIWARA、Yohko AKIYAMA(nee KONDO)、Hisashi ISHII

  DOI：10.1248/cpb.43.1281

  日期：——

  The Fischer indolization of ethyl pyruvate 2-[2-(trifluoromethyl)phenyl]phenylhydrazone (5) gave two indolic products, ethyl 7-(trifluoromethyl)-1-phenylindole-2-carboxylate (12) as a minor product and ethyl 1-[2-(trifluoromethyl)phenyl]indole-2-carboxylate (13) as a major product. This result shows that the Fischer indolization occurred on the more electron-rich phenyl group. In the Goldberg reaction to prepare 13 from ethyl indole-2-carboxylate (15) and o- (21) or m-bromo-α, α, α-trifluotoluene (23), it was found that Goldberg reaction proceeds via a benzyne mechanism, at least in part, in a sterically crowded situation.

  Fischer吲哚合成法对乙基丙二酸酯2-[2-(三氟甲基)苯基]苯肼（5）进行反应，得到两个吲哚产物，分别是少量产物乙基7-(三氟甲基)-1-苯基吲哚-2-羧酸酯（12）和主要产物乙基1-[2-(三氟甲基)苯基]吲哚-2-羧酸酯（13）。这一结果表明，Fischer吲哚合成发生在电子云密度更高的苯基上。在通过Goldberg反应由乙基吲哚-2-羧酸酯（15）和邻位（21）或间位溴-α, α, α-三氟甲苯（23）制备13的过程中发现，Goldberg反应至少在一定程度上通过苯炔机制进行，尤其是在空间位阻较大的情况下。
• SYNTHESIS OF PHENOTHIAZINE DERIVATIVES FOR USE AS ANTIOXIDANTS
  作者：NATHAN L. SMITH

  DOI：10.1021/jo01151a033

  日期：1950.9
• Cupric acetate mediated N-arylation by arylboronic acids: A preliminary investigation into the scope of application
  作者：Darren J Cundy、Stewart A Forsyth

  DOI：10.1016/s0040-4039(98)01735-3

  日期：1998.10

  A range of NH substrates of varying nucleophilicity were reacted with a selection of electronically diverse aryl boronic acids in the presence of cupric acetate in order to evaluate the generality of a previously described N-arylation procedure. The results of that investigation are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of Diarylamines Catalyzed by Iron Salts
  作者：Arkaitz Correa、Mónica Carril、Carsten Bolm

  DOI：10.1002/chem.200802018

  日期：2008.12.8