N-(p-methoxyphenyl) bromodifluoroacetimidoyl chloride

• 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-(p-methoxyphenyl) bromodifluoroacetimidoyl chloride
• 英文别名: 2-bromo-2,2-difluoro-N-(4-methoxyphenyl)acetimidoyl chloride；2-bromo-2,2-difluoro-N-(4-methoxyphenyl)ethanimidoyl chloride
• 化学式: C₉H₇BrClF₂NO
• 分子量: 298.514
• InChiKey: WTGXXUKLKQPLNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(p-methoxyphenyl) bromodifluoroacetimidoyl chloride 在 Wilkinson's catalyst 、 正丁基锂 、 silver carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 3.33h， 生成 N-(2-(tert-butyl)-6,6-difluoro-8-methoxypyrrolo[2,1-a]isoquinolin-5(6H)-ylidene)-4-methoxyaniline
  参考文献：
  名称：

  Rh-catalyzed intramolecular sp2 C–H bond difluoromethylenation

  摘要：

  一种新的Rh催化的CF2Br基团与吲哚或吡咯的2-芳基间的分子内偶联反应被提出，经过C–H键活化。该反应代表了将二氟亚甲基团引入有机化合物的新方式。初步的机理研究表明，该反应可能不是通过传统的自由基途径进行的。

  DOI：

  10.1039/c2cc30207a

文献信息

• β-Bromodifluoromethyl β-enaminoketones: versatile synthetic intermediates for synthesis of CF2-containing compounds
  作者：Yong-Ming Wu、Ya Li、Juan Deng

  DOI：10.1016/j.tetlet.2005.06.002

  日期：2005.8

  A series of N-aryl β-bromodifluoromethyl β-enaminoketones were regioselectively synthesized in good yield by the reaction of N-aryl bromodifluoroacetimidoyl chlorides with methyl ketones. β-Bromodifluoromethyl β-enaminoketones smoothly cyclized to give a novel class of cyclic (2,2-difluoro-5-phenyl-furan-3-ylidene)-aryl-amines under basic condition. An intramolecular halophilic substitution mechanism

  通过使N-芳基溴二氟乙酰亚胺基氯与甲基酮反应，以高产率区域选择性地合成了一系列N-芳基β-溴二氟甲基β-烯胺酮。β-溴二氟甲基β-烯胺酮在碱性条件下平稳环化，得到一类新型的环状（2,2-二氟-5-苯基-呋喃-3-亚烷基）-芳基胺。提出了分子内的嗜盐取代机制。
• Rhodium-Catalyzed Intramolecular Difluoromethylenative Dearomatization of Phenols
  作者：Yajun Li、Lisi Zhang、Li Zhang、Yongming Wu、Yuefa Gong

  DOI：10.1002/ejoc.201301225

  日期：2013.12

  Rhodium-catalyzed intramolecular difluoromethylenative dearomatization of phenols to yield azaspirocyclohexadienones containing all-carbon quaternary centers in good to excellent yields was developed. A variety of functional groups proved compatible with

  开发了铑催化的酚类分子内二氟亚甲基脱芳构化，以产生含有全碳季中心的氮杂螺环己二烯酮，收率良好至极好。各种官能团被证明与
• Facile synthesis of α-fluoro substituted amidines from imidoyl chlorides and some of its application
  作者：Yong-Ming Wu、Min Zhang、Yi-Qun Li

  DOI：10.1016/j.jfluchem.2006.06.008

  日期：2006.9

  A series of α-fluoro subustituted amidines were synthesized from corresponding fluorinated imidoyl chlorides in good to excellent yields and some of its applications are outlined in our programs.

  从相应的氟化亚氨酰氯合成了一系列α-氟取代的am，收率良好至优异，我们的程序概述了其一些应用。
• An efficient method to access 2-fluoroalkylbenzimidazoles by PIDA oxidation of amidines
  作者：Jiangtao Zhu、Zixian Chen、Haibo Xie、Shan Li、Yongming Wu

  DOI：10.1016/j.jfluchem.2011.06.007

  日期：2012.1

  A mild and practical strategy for the synthesis of 2-bromodifluoromethyl (or trifluoromethyl)-1H-benzimidazoles via PIDA-mediated oxidative intramolecular cyclization of the fluorinated amidines is described. The approach has the advantages of superior yields, excellent functional groups tolerance and mild reaction conditions. (C) 2011 Elsevier B.V. All rights reserved.
• Rh-catalyzed intramolecular sp2 C–H bond difluoromethylenation
  作者：Yajun Li、Jiangtao Zhu、Haibo Xie、Shan Li、Dongjie Peng、Zhengke Li、Yongming Wu、Yuefa Gong

  DOI：10.1039/c2cc30207a

  日期：——

  A new Rh-catalyzed intramolecular coupling reaction of a CF2Br group with a 2-aryl of indole or pyrrolevia C–H bond activation is presented. This reaction represents a new way of incorporating difluoromethylene groups into organic compounds. Preliminary mechanistic studies suggest that this reaction might not occur via a conventional free radical pathway.

  一种新的Rh催化的CF2Br基团与吲哚或吡咯的2-芳基间的分子内偶联反应被提出，经过C–H键活化。该反应代表了将二氟亚甲基团引入有机化合物的新方式。初步的机理研究表明，该反应可能不是通过传统的自由基途径进行的。