(E)-N,3-bis(4-chlorophenyl)acrylamide | 110179-65-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N,3-bis(4-chlorophenyl)acrylamide
• 英文别名: 4-chloro-trans-cinnamic acid-(4-chloro-anilide)；4-Chlor-trans-zimtsaeure-(4-chlor-anilid)；(2E)-N,3-bis(4-chlorophenyl)prop-2-enamide；(E)-N,3-bis(4-chlorophenyl)prop-2-enamide
• CAS: 110179-65-2
• 化学式: C₁₅H₁₁Cl₂NO
• 分子量: 292.164
• InChiKey: VJZUOEFCTHGIMC-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-4,4'-(prop-1-ene-1,3-diyl)bis(chlorobenzene) 在 叠氮基三甲基硅烷 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 iron(II) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以81%的产率得到(E)-N,3-bis(4-chlorophenyl)acrylamide
  参考文献：
  名称：

  铁催化的C ？H和C ？C键裂解：直接从简单烃中酰胺化的方法

  摘要：

  起作用的东西：标题反应在叠氮化物和水的存在下进行，以高收率提供酰胺，可用于扩环策略以生成内酰胺。根据实验结果提出了一种机理。该反应提供了一种功能化简单易得的碳氢化合物的新方法。DDQ = 2,3-二氯-5,6-二氰基-1,4-苯醌。

  DOI：

  10.1002/anie.201106112

文献信息

• DDQ-promoted direct transformation of benzyl hydrocarbons to amides via tandem reaction of the CDC reaction and Beckmann rearrangement
  作者：Jun Qiu、Ronghua Zhang

  DOI：10.1039/c3ob41218k

  日期：——

  An atom-efficient and transition metal-free approach to amides from the corresponding benzyl hydrocarbons through C–H and C–C bond cleavage has been developed. Mechanistic studies have shown that a DDQ-promoted cross-dehydrogenative coupling (CDC) reaction with subsequent oxidation and rearrangement are involved in this transformation.

  开发了一种通过C-H和C-C键断裂，从相应的苄基烃高效、无需过渡金属的原子到酰胺合成的方法。机理研究表明，这种转化涉及DDQ促进的交叉脱氢偶联（CDC）反应、随后氧化和重排。
• Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source
  作者：Balaji V. Rokade、Karthik Gadde、Kandikere Ramaiah Prabhu

  DOI：10.1002/ejoc.201500010

  日期：2015.4

  synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation

  在2,3-二氯-5存在下，以仲醇、Cu(ClO4)2·6H2O为催化剂，以叠氮化三甲基甲硅烷(TMSN3)为氮源，探索了一种温和、简便的酰胺合成方法。 ,6-二氰基对苯醌 (DDQ) 在环境温度下。该方法已成功地适用于直接从其相应的醇制备叠氮化物，并在 ω-卤代叠氮化物的形成和烯丙醇在苄醇部分存在下的叠氮化中提供出色的化学选择性。此外，该策略为合成可作为 β-氨基酸前体的叠氮化物提供了机会。
• Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides
  作者：Tomas Strharsky、Dominika Pindjakova、Jiri Kos、Lucia Vrablova、Hana Michnova、Jan Hosek、Nicol Strakova、Veronika Lelakova、Lenka Leva、Lenka Kavanova、Michal Oravec、Alois Cizek、Josef Jampilek

  DOI：10.3390/ijms23063159

  日期：——

  A series of eighteen 4-chlorocinnamanilides and eighteen 3,4-dichlorocinnamanilides were designed, prepared and characterized. All compounds were evaluated for their activity against gram-positive bacteria and against two mycobacterial strains. Viability on both cancer and primary mammalian cell lines was also assessed. The lipophilicity of the compounds was experimentally determined and correlated together with other physicochemical properties of the prepared derivatives with biological activity. 3,4-Dichlorocinnamanilides showed a broader spectrum of action and higher antibacterial efficacy than 4-chlorocinnamanilides; however, all compounds were more effective or comparable to clinically used drugs (ampicillin, isoniazid, rifampicin). Of the thirty-six compounds, six derivatives showed submicromolar activity against Staphylococcus aureus and clinical isolates of methicillin-resistant S. aureus (MRSA). (2E)-N-[3,5-bis(trifluoromethyl)phenyl]- 3-(4-chlorophenyl)prop-2-enamide was the most potent in series 1. (2E)-N-[3,5-bis(Trifluoromethyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide, (2E)-3-(3,4-dichlorophenyl)-N-[3-(trifluoromethyl)phenyl]prop-2-enamide, (2E)-3-(3,4-dichloro- phenyl)-N-[4-(trifluoromethyl)phenyl]prop-2-enamide and (2E)-3-(3,4-dichlorophenyl)- N-[4-(trifluoromethoxy)phenyl]prop-2-enamide were the most active in series 2 and in addition to activity against S. aureus and MRSA were highly active against Enterococcus faecalis and vancomycin-resistant E. faecalis isolates and against fast-growing Mycobacterium smegmatis and against slow-growing M. marinum, M. tuberculosis non-hazardous test models. In addition, the last three compounds of the above-mentioned showed insignificant cytotoxicity to primary porcine monocyte-derived macrophages.

  设计、制备并表征了18种4-氯肉桂酰胺和18种3,4-二氯肉桂酰胺。评估了所有化合物对革兰氏阳性菌和两种分枝杆菌菌株的活性。还评估了化合物在癌细胞和原代哺乳动物细胞系上的存活率。实验测定了化合物的亲脂性，并将其与所制备衍生物的其他物理化学性质相关联，以探究其生物活性。3,4-二氯肉桂酰胺表现出更广泛的作用谱和更高的抗菌效力，而所有化合物都比临床使用的药物（氨苄青霉素、异烟肼、利福平）更有效或相当。在36种化合物中，有6种衍生物对金黄色葡萄球菌和甲氧西林耐药金黄色葡萄球菌（MRSA）表现出亚微米级的活性。在第一系列中，(2E)-N-[3,5-双(三氟甲基)苯基]-3-(4-氯苯基)丙-2-烯酰胺是最有效的。在第二系列中，(2E)-N-[3,5-双(三氟甲基)苯基]-3-(3,4-二氯苯基)丙-2-烯酰胺、(2E)-3-(3,4-二氯苯基)-N-[3-(三氟甲基)苯基]丙-2-烯酰胺、(2E)-3-(3,4-二氯苯基)-N-[4-(三氟甲基)苯基]丙-2-烯酰胺和(2E)-3-(3,4-二氯苯基)-N-[4-(三氟甲氧基)苯基]丙-2-烯酰胺是最活跃的，并且除了对S. aureus和MRSA的活性外，还高度活跃于肠球菌和万古霉素耐药肠球菌分离株以及快速生长的结核分枝杆菌和缓慢生长的海水分枝杆菌等非危险性试验模型。此外，上述最后三种化合物对初代猪单核细胞衍生的巨噬细胞具有极小的细胞毒性。
• Kim, Tae-Hyoung; Huh, Chul; Lee, Bon-Su, Journal of the Chemical Society. Perkin transactions II, 1995, # 12, p. 2257 - 2262
  作者：Kim, Tae-Hyoung、Huh, Chul、Lee, Bon-Su、Lee, Ikchoon

  DOI：——

  日期：——
• School Nurses Identify Barriers and Solutions to Implementing a School-Based Hepatitis B Immunization Program
  作者：Andrea D. Guajardo、Amy B. Middleman、Kim M. Sansaricq

  DOI：10.1111/j.1746-1561.2002.tb06531.x

  日期：2002.3