(E)-3-(2-chlorophenyl)-N-phenyl-2-propenamide | 935430-61-8

• 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)-3-(2-chlorophenyl)-N-phenyl-2-propenamide
• 英文别名: (E)-3-(2-chlorophenyl)-N-phenylacrylamide；2-chloro-trans-cinnamic acid anilide；2-Chlor-trans-zimtsaeure-anilid；N1-phenyl-3-(2-chlorophenyl)acrylamide；(E)-3-(2-chlorophenyl)-N-phenylprop-2-enamide
• CAS: 935430-61-8
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: SPGGGKNPDWVLRC-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 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

• 作为反应物：
  描述：

  (E)-3-(2-chlorophenyl)-N-phenyl-2-propenamide 、 苯硼酸 在 bis(η3-allyl-μ-chloropalladium(II)) 、 2-(二环己基膦)3,6-二甲氧基-2′,4′,6′-三异丙基-1,1′-联苯 、 2Rh⁽¹⁺⁾*2Cl^(1-)*2C₈H₇CH₃CH(CH₃)2COOC₆H₃(CH₃)2=(RhCl(C₈H₇CH₃CH(CH₃)2COOC₆H₃(CH₃)2))2 、 potassium hydroxide 作用下， 以 甲醇 、 2-甲基-2-丁醇 为溶剂， 反应 18.08h， 以60%的产率得到(S)-1,4-diphenyl-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  顺序铑/钯催化：在非手性和手性配体存在下二氢喹啉酮的对映选择性形成

  摘要：

  非手性和手性配体的相容组合可用于铑/钯催化，以实现高度对映选择性的多米诺反应。催化速率的差异和配体干扰的最小影响赋予了多米诺骨牌序列控制权。“全合一” 1,4-共轭的芳基化和C 通过顺序的Rh / Pd催化下Ñ交叉耦合提供了访问对映体富集二氢喹啉酮积木。

  DOI：

  10.1002/anie.201407400
• 作为产物：
  描述：

  3-苯胺基-3-羰基丙酸 生成 (E)-3-(2-chlorophenyl)-N-phenyl-2-propenamide
  参考文献：
  名称：

  Pandya; Pandya, Proceedings - Indian Academy of Sciences, Section A, 1943, vol. 17, p. 1,4

  摘要：

  DOI：

文献信息

• 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。
• INHIBITORS OF VIRAL REPLICATION
  申请人：Beigelman Leonid

  公开号：US20090099186A1

  公开（公告）日：2009-04-16

  The embodiments provide compounds of the general Formulas I-IV, as well as compositions, including pharmaceutical compositions, comprising a subject compound. The embodiments further provide treatment methods, including methods of treating a hepatitis C virus infection and methods of treating liver fibrosis, the methods generally involving administering to an individual in need thereof an effective amount of a subject compound or composition.

  实施例提供了一般公式I-IV的化合物，以及包括主题化合物的组合物，包括药物组合物。实施例还提供了治疗方法，包括治疗丙型肝炎病毒感染的方法和治疗肝纤维化的方法，这些方法通常涉及向需要的个体施用主题化合物或组合物的有效量。
• Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction
  作者：Jun Qiu、Ronghua Zhang

  DOI：10.1039/c3ob42444h

  日期：——

  arylpropynes and hydroxylamine hydrochloride through sp3 C–H and C–C bond cleavage has been achieved with DDQ as an oxidant. The mechanistic study shows that the acrylamides are formed through a three-step tandem sequence, including cross-dehydrogenative-coupling (CDC) reaction, aza-Meyer–Schuster rearrangement and Beckmann rearrangement.

  使用DDQ作为氧化剂，可以通过sp 3 C–H和C–C键断裂在芳基丙炔和羟胺盐酸盐之间形成一种新颖且无金属的丙烯酰胺。机理研究表明，丙烯酰胺是通过三步串联序列形成的，包括交叉脱氢偶联（CDC）反应，Aza-Meyer-Schuster重排和Beckmann重排。
• Synthesis of a series of unsaturated ketone derivatives as selective and reversible monoamine oxidase inhibitors
  作者：Ji Won Choi、Bo Ko Jang、Nam-chul Cho、Jong-Hyun Park、Seul Ki Yeon、Eun Ji Ju、Yong Sup Lee、Gyoonhee Han、Ae Nim Pae、Dong Jin Kim、Ki Duk Park

  DOI：10.1016/j.bmc.2015.08.012

  日期：2015.10

  We have synthesized three categories of alpha,beta-unsaturated carbonyl derivatives and evaluated their MAO-A and MAO-B inhibitory activities. Among them, compound 10b including alpha, beta-unsaturated ketone group showed the most potent and selective MAO-B inhibitory activity (IC50 human MAO-B 16 nM, >6000-fold selective vs MAO-A) and compound 10b exhibited good reversibility compared with selegiline, a well-known irreversible MAO-B inhibitor. However, both a, b-unsaturated amide and ester derivatives exhibited weaker MAO-B inhibition potencies. The docking studies provided insights into the possible binding modes and the key interaction sites of the synthesized MAO-B inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.
• Design, synthesis, antiviral evaluation, and In silico studies of acrylamides targeting nsP2 from Chikungunya virus
  作者：Beatriz Gois de Souza、Shweta Choudhary、Gabriel Gomes Vilela、Gabriel Felipe Silva Passos、Clara Andrezza Crisóstomo Bezerra Costa、Johnnatan Duarte de Freitas、Grazielle Lobo Coelho、Júlia de Andrade Brandão、Leticia Anderson、Ênio José Bassi、João Xavier de Araújo-Júnior、Shailly Tomar、Edeildo Ferreira da Silva-Júnior

  DOI：10.1016/j.ejmech.2023.115572

  日期：2023.10