N-(4-chlorophenyl)-2,2,2,-trichloroacetamide | 2877-13-6

• 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: N-(4-chlorophenyl)-2,2,2,-trichloroacetamide
• 英文别名: N-4-chlorophenyltrichloroacetamide；trichloro-acetic acid-(4-chloro-anilide)；Trichlor-essigsaeure-(4-chlor-anilid)；2,2,2-trichloro-N-(4-chlorophenyl)-acetamide；2,2,2,4'-tetrachloro-acetanilide；α,α,α-Trichlor-p-chloracetanilid；Acetamide, 2,2,2-trichloro-N-(4-chlorophenyl)-；2,2,2-trichloro-N-(4-chlorophenyl)acetamide
• CAS: 2877-13-6
• 化学式: C₈H₅Cl₄NO
• mdl: MFCD00028819
• 分子量: 272.946
• InChiKey: CWUXLDOMGYBJFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(4-chlorophenyl)-2,2,2,-trichloroacetamide 在 2,4-双(对甲苯基硫代)-1,3-二硫杂-2,4-二磷杂环丁烷-2,4-二硫化物 作用下， 以 甲苯 为溶剂， 生成 N-4-chlorophenyltrichlorothioacetamide
  参考文献：
  名称：

  Preparation of trichlorothioacetamides and their unexpected rearrangement to thiooxamides

  摘要：

  The preparation of several N-monosubstituted trichlorothioacetamides by thionation of the corresponding acetamides, with the use of Heimgartner's reagent is described. In contrast to the corresponding amides which umdergo base-induced beta-elimination of chloroform, the title compounds undergo an unexpected rearrangement to thiooxamides. The reaction mechanism is discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02080-2
• 作为产物：
  描述：

  六氯丙酮 、 对氯苯胺 在 正己烷 作用下， 生成 N-(4-chlorophenyl)-2,2,2,-trichloroacetamide
  参考文献：
  名称：

  Sukornick, Organic Syntheses, 1960, vol. 40, p. 103

  摘要：

  DOI：

文献信息

• A novel synthesis of isocyanates and ureas via β-elimination of haloform
  作者：S. Braverman、M. Cherkinsky、L. Kedrova、A. Reiselman

  DOI：10.1016/s0040-4039(99)00372-x

  日期：1999.4

  isocyanates via base-induced β-elimination of haloform N-monosubstituted trihaloacetamides is described. The rate of reaction exhibits a strong dependence on the nature of the trihalomethyl group. Thus, while the reaction of tribromoacetamides proceeds at room temperature and the reaction of trichloroacetamides requires heating in polar solvents, no reaction could be observed for any of the corresponding

  描述了通过卤代N-单取代的三卤代乙酰胺的碱诱导的β-消除新合成的异氰酸酯。反应速率显示出对三卤代甲基基团的强烈依赖性。因此，尽管三溴乙酰胺的反应在室温下进行并且三氯乙酰胺的反应需要在极性溶剂中加热，但是对于任何相应的三氟衍生物都没有观察到反应。从稳定且容易获得的三卤代乙酰胺中去除卤素的这种新颖的β-消除方法可用于尿素的“一锅法”合成，避免了使用光气和分离异氰酸酯。
• Photoinduced Alcoholysis of Trihaloacetyl Group
  作者：Yasuji Izawa、Katsuhiro Ishiguro、Hideo Tomioka

  DOI：10.1246/bcsj.56.951

  日期：1983.3

  Photolysis of trichloroacetamide in nondegassed methanol gave methyl oxanilate (13–44%), along with carbamate (3–20%) and amine (4–12%). Similar irradiation of other trichloroacetyl derivatives of aliphatic ketone, aldehyde, and acetate afforded only radical product. The results are interpreted in terms of the mechanism involving electron transfer of the radical pair.

  三氯乙酰胺在未脱气的甲醇中的光解得到草胺酸甲酯 (13-44%)、氨基甲酸酯 (3-20%) 和胺 (4-12%)。脂肪族酮、醛和乙酸酯的其他三氯乙酰衍生物的类似辐照仅提供自由基产物。根据涉及自由基对电子转移的机制来解释结果。
• Die Darstellung von N-Trichloracetaniliden unter der Anwendung von Phosphoroxychlorid
  作者：Francisco Antonio Berti、Lizwaldo Mario Ziti

  DOI：10.1002/ardp.19522850806

  日期：——
• Microwave Promoted Environmentally Benign Synthesis of 2-Aminobenzothiazoles and Their Urea Derivatives
  作者：Zheng Li、Shuxiu Xiao、Guoqiang Tian、Anguo Zhu、Xu Feng、Jing Liu

  DOI：10.1080/10426500701578506

  日期：2008.4.18

  2-Aminobenzothiazoles were efficiently synthesized using stable, crystalline tetrabutylammonium tribromide instead of toxic, corrosive liquid bromine under solvent-free and microwave irradiation condition. Furthermore, benzothiazol-2-ylureas were synthesized in good to high yield by reactions of 2-aminobenzothiazoles with N-trichloroacetanilides, which were used as a substitute for toxic, unstable isocyanates, under microwave irradiation condition. This protocol has advantages of no utilization of hazardous chemicals, rapid reaction rate, high yield, and easy work-up procedure.
• Bew, Clive; Joshi, Virginia Otero de; Gray, Jim, Journal of the Chemical Society. Perkin transactions I, 1982, p. 945 - 948
  作者：Bew, Clive、Joshi, Virginia Otero de、Gray, Jim、Kaye, Perry T.、Meakins, G. Denis

  DOI：——

  日期：——

表征谱图