N-(2-chloro-2-propenyl)-2-chloroaniline | 133932-64-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-chloro-2-propenyl)-2-chloroaniline
• 英文别名: 2-chloro-N-(2-chloroallyl)aniline；2-chloro-N-(2-chloroprop-2-enyl)aniline
• CAS: 133932-64-6
• 化学式: C₉H₉Cl₂N
• mdl: MFCD12797681
• 分子量: 202.083
• InChiKey: AUQCCKPFAIYATM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(2-chloro-2-propenyl)-2-chloroaniline 以38%的产率得到
  参考文献：
  名称：

  FOX, MARYE ANNE;CHANDLER, DANIEL A.;LEE, CHANGJIN, J. ORG. CHEM., 56,(1991) N0, C. 3246-3255

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-二氯丙烯 、 邻氯苯胺 在 potassium carbonate 作用下， 反应 12.0h， 以15%的产率得到N-(2-chloro-2-propenyl)-2-chloroaniline
  参考文献：
  名称：

  Electrocatalytic coupling of aryl halides with (1,2-bis(di-2-propylphosphino)benzene)nickel(0)

  摘要：

  Dibromo- and dichloro(1,2-bis(di-2-propylphosphino)benzene)nickel(II) is compared with tetrakis(triphenylphosphino)nickel(II) as an electrocatalyst for the reductive coupling of aryl halides. In many of the reactions examined, dehalogenation of the substrate predominated over coupling; however, preparative yields of biphenyls as high as 96% can be obtained with aryl chlorides and 2 mol % of the title catalyst in polar, coordinating solvents. Experimental factors governing the efficiency of these reactions are discussed, and possible mechanisms for coupling and catalyst deactivation are considered. Much better selectivity for aryl chlorides is attained in electroreductive couplings catalyzed by the title compound, whereas electrocatalysis with (Ph3P)4NiCl2 allows for selective intra- and intermolecular coupling at aryl bromide and vinyl chloride sites. Modest yields of cyclization products can be attained with either electrocatalyst in the presence of appropriately functionalized aryl or vinyl halides.

  DOI：

  10.1021/jo00010a014

文献信息

• Highly Efficient Synthesis of New α-Arylamino-α′-chloropropan-2-ones via Oxidative Hydrolysis of Vinyl Chlorides Promoted by Calcium Hypochlorite
  作者：Vittorio Pace、Fernando Martínez、María Fernández、José V. Sinisterra、Andrés R. Alcántara

  DOI：10.1002/adsc.200900565

  日期：2009.12

  The oxidative hydrolysis of different trifluoroacetyl-protected N-(2-chloroallyl)anilines, promoted by calcium hypochlorite, is able to yield several not previously described α-arylamino-α′-chloropropan-2-ones, very valuable building blocks that are useful as precursors of several drugs, in excellent yields and short reaction times. The main requirement of the reaction for avoiding the undesired aromatic

  由次氯酸钙促进的不同三氟乙酰基保护的N-（2-氯烯丙基）苯胺的氧化水解能够产生几种先前未描述的α-芳基氨基-α'-氯丙烷-2-酮，这是非常有用的重要组成部分作为几种药物的前体，具有优异的收率和较短的反应时间。通过使用易于形成和除去的N-三氟乙酰基，可以有效地解决为避免不希望的芳族氯化反应（N-保护）而进行的反应的主要要求。因此，可以使用一锅法进行氧化水解-脱保护步骤，从而在非常短的反应时间内获得定量的产率。