(E)-2-cyano-3-(2,4-dichlorophenyl)acrylamide | 1352550-05-0

• 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)-2-cyano-3-(2,4-dichlorophenyl)acrylamide
• 英文别名: (E)-2-cyano-3-(2,4-dichlorophenyl)prop-2-enamide
• CAS: 1352550-05-0
• 化学式: C₁₀H₆Cl₂N₂O
• 分子量: 241.076
• InChiKey: XLEXVFCXCZKVRX-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-cyano-3-(2,4-dichlorophenyl)acrylamide 、 噻莫西酸 、 苊醌 在 sodium chloride 作用下， 以 水 为溶剂， 反应 0.58h， 以88%的产率得到6'-cyano-7'-(2,4-dichlorophenyl)-2-oxo-3',6',7',7a'-tetrahydro-1'H,2H-spiro[acenaphthylene-1,5'-pyrrolo[1,2-c]thiazole]-6'-carboxamide
  参考文献：
  名称：

  Imposed hydrophobic interactions by NaCl: accountable attribute for the synthesis of spiro[acenaphthylene-1,5′-pyrrolo[1,2-c]thiazole] derivatives via 1,3-dipolar cycloaddition reaction in aqueous medium

  摘要：

  水疏水性对在水介质中通过1,3-双极环加成反应合成螺[芴-1,5′-吡咯[1,2-c]噻唑]衍生物的重要性进行了概述。

  DOI：

  10.1039/c5gc02816g
• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 氰乙酰胺 在 N-甲基哌嗪 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以52%的产率得到(E)-2-cyano-3-(2,4-dichlorophenyl)acrylamide
  参考文献：
  名称：

  Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases

  摘要：

  The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a K(i)-value of 35.7 mu M at the Dengue and 44.6 mu M at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.061

文献信息

• Oxidative Olefination of Benzylamine with an Active Methylene Compound Mediated by Hypervalent Iodine (III)
  作者：Bapurao D. Rupanawar、Sruthi M. Veetil、Gurunath Suryavanshi

  DOI：10.1002/ejoc.201900970

  日期：2019.9.30

  Hypervalent iodine mediates the oxidative olefination of amines with active methylene compounds for the formation of electrophilic alkenes under mild reaction conditions in good to excellent yields.

  高价碘介导胺与活性亚甲基化合物的氧化烯化反应，可在温和的反应条件下以良好至极好的收率形成亲电烯烃。
• Triflic acid-catalyzed metal-free synthesis of (<i>E</i>)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones
  作者：Bapurao D. Rupanwar、Santosh S. Chavan、Anil M. Shelke、Gurunath M. Suryavanshi

  DOI：10.1039/c7nj05169g

  日期：——

  efficient synthesis of biologically active (E)-2-cyanoacrylamides and 3-substituted azetidine-2,4-diones has been reported with 64–94% yields under metal-free conditions. The reaction proceeds through sequential Knoevenagel condensation/stereoselective in situ monohydration of nitrile or C–N cyclization protocol in one-pot. The attractive features of this tandem process are moderate reaction conditions

  据报道，在无金属条件下，TfOH催化可高效合成具有生物活性的（E）-2-氰基丙烯酰胺和3-取代的氮杂环丁烷2,4-二酮，收率为64-94％。反应通过一锅顺序进行的Knoevenagel缩合反应/腈选择性地原位单水合或CN环化方案进行。该串联方法的吸引人的特征是中等反应条件，高原子经济性，广泛的底物范围，克级反应和易于操作。
• Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases
  作者：Christoph Nitsche、Christian Steuer、Christian D. Klein

  DOI：10.1016/j.bmc.2011.10.061

  日期：2011.12

  The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a K(i)-value of 35.7 mu M at the Dengue and 44.6 mu M at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Imposed hydrophobic interactions by NaCl: accountable attribute for the synthesis of spiro[acenaphthylene-1,5′-pyrrolo[1,2-c]thiazole] derivatives via 1,3-dipolar cycloaddition reaction in aqueous medium
  作者：Anshu Dandia、Vijay Parewa、Sukhbeer Kumari、Sarika Bansal、Amit Sharma

  DOI：10.1039/c5gc02816g

  日期：——

  The significance of hydrophobicity for the synthesis of spiro[acenaphthylene-1,5′-pyrrolo[1,2-c]thiazole] derivatives by a 1,3-dipolar cycloaddition reaction in aqueous medium is outlined.

  水疏水性对在水介质中通过1,3-双极环加成反应合成螺[芴-1,5′-吡咯[1,2-c]噻唑]衍生物的重要性进行了概述。