(E)-N,N-diethyl-2,2-difluoro-4-phenylbut-3-enamide | 1239497-42-7

• 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: (E)-N,N-diethyl-2,2-difluoro-4-phenylbut-3-enamide
• CAS: 1239497-42-7
• 化学式: C₁₄H₁₇F₂NO
• 分子量: 253.292
• InChiKey: MDQVCMGLYLSUGG-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  [(Z)-2-溴乙烯基]苯 、 2-bromo-N,N-diethyl-2,2-difluoroacetamide 在 锰 、 sodium iodide 、 iron(II) chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到(E)-N,N-diethyl-2,2-difluoro-4-phenylbut-3-enamide
  参考文献：
  名称：

  双 Fe/Pd 催化还原交叉偶联：用烯基溴化物和溴二氟甲烷构建 gem-二氟亚丙基

  摘要：

  已经公开了一种前所未有的铁/钯催化的烯基溴和溴二氟甲烷与锰作为还原剂的还原交叉偶联。各种官能团具有良好的耐受性，以中等至良好的产率提供各种取代的偕二氟亚丙基。初步机制研究排除了这种新反应的自由基途径。

  DOI：

  10.1002/ejoc.202101252

文献信息

• （E）-4-芳基-2,2-二氟-3-丁烯酸类衍生物的制备方法
  申请人：昆明理工大学

  公开号：CN113511972A

  公开（公告）日：2021-10-19

  本发明公开一种（E）‑4‑芳基‑2，2‑二氟‑3‑丁烯酸类衍生物的制备方法，属于医药中间体及有机合成技术领域，本发明以（E）‑1‑芳基‑2‑溴乙烯、2，2‑二氟‑2‑溴乙酸类衍生物为原料，在铁/钯共催化剂的协同催化下发生还原偶联反应，生成（E）‑4‑芳基‑2，2‑二氟‑3‑丁烯酸类衍生物；本发明所合成的（E）‑4‑芳基‑2，2‑二氟‑3‑丁烯酸类衍生物含有偕二氟烯丙基结构单元，可作为潜在的候选药物，亦可为引入偕二氟烯丙基提供一种全新的方式。
• Copper-Catalyzed C–H Difluoroalkylations and Perfluoroalkylations of Alkenes and (Hetero)arenes
  作者：Xiaoyang Wang、Shuang Zhao、Jing Liu、Dingsheng Zhu、Minjie Guo、Xiangyang Tang、Guangwei Wang

  DOI：10.1021/acs.orglett.7b01712

  日期：2017.8.18

  A general and facile synthetic method for C(sp2)–H difluoroalkylations and perfluoroalkylations of alkenes and (hetero)arenes with commercially available fluoroalkyl halides has been developed with a copper-amine catalyst system. This method is characterized by high yields, mild reaction conditions, low-cost catalyst, broad substrate scope, and excellent functional group compatibility, therefore providing

  已经开发了一种使用铜胺催化剂体系开发的用于烯烃和（杂）芳烃的C（sp 2）-H二氟烷基化和全氟烷基化的通用且简便的合成方法。该方法的特征在于高收率，温和的反应条件，低成本的催化剂，广泛的底物范围和优异的官能团相容性，因此为各种二氟烷基和全氟烷基取代的烯烃和（杂）芳烃提供了方便的合成策略。
• Copper-mediated regioselective hydrodifluoroalkylation of alkynes
  作者：Xiaorui Feng、Xiaoyang Wang、Hongtai Chen、Xiangyang Tang、Minjie Guo、Wentao Zhao、Guangwei Wang

  DOI：10.1039/c8ob00256h

  日期：——

  A highly regioselective copper-mediated hydrodifluoroalkylation of alkynes with ethyl bromodifluoroacetate or bromodifluoroacetamides has been developed. This strategy provides straightforward access to a variety of difluoroalkylated alkenes under mild reaction conditions with low-cost cuprous bromide and metabisulfite as reduction agents. A wide range of alkynes are applicable under these reaction

  已经开发了具有高区域选择性的铜介导的炔烃与溴代二氟乙酸乙酯或溴代二氟乙酰胺的氢二氟烷基化。该策略可在温和的反应条件下以低成本的溴化亚铜和偏亚硫酸氢盐作为还原剂，直接获得各种二氟烷基化烯烃。在这些反应条件下，可以使用多种炔烃。出色的功能基团相容性以及良好的区域选择性和立体选择性是这一转变的显着特征。
• Copper-Mediated Fluoroalkylation Reactions with Iododifluoroacetamides: Controlling the Selectivity among Cross-Coupling, Intramolecular Cyclization, and Homocoupling Reactions
  作者：Jieming Zhu、Wei Zhang、Laijun Zhang、Jun Liu、Ji Zheng、Jinbo Hu

  DOI：10.1021/jo1005262

  日期：2010.8.20

  Cu-mediated fluoroalkylation reactions with iododifluoroacetamides I have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R-1 = alkyl and R-2 = aryl groups, or when R-1 = R-2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R-1 = R-2 = alkyl groups, or when R-1 = H and R-2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.