β-(2-thienylmethylidene)(cyano)acetamide | 97006-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: β-(2-thienylmethylidene)(cyano)acetamide
• 英文别名: (E)-2-cyano-3-(thiophen-2-yl)acrylamide；(E)-2-cyano-3-(2-thienyl)acrylamide；2-cyano-3-(thiophen-2-yl)acrylamide；2-cyano-3-(2-thienyl)propenamide；(2E)-2-cyano-3-(thiophen-2-yl)prop-2-enamide；(E)-2-cyano-3-thiophen-2-ylprop-2-enamide
• CAS: 97006-41-2
• 化学式: C₈H₆N₂OS
• 分子量: 178.214
• InChiKey: BTCIBXVDLXOYIT-GQCTYLIASA-N

物化性质

• 沸点：
  432.4±45.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 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：
  95.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  β-(2-thienylmethylidene)(cyano)acetamide 、 苯乙酮 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 3-cyano-6-phenyl-4-(thiophen-2'-yl)-2(1H)-pyridone
  参考文献：
  名称：

  Elgemeie, Galal Eldin Hamza; Zohdi, Hussein Fouad; Sherif, Sherif Mourad, Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 54, # 1/4, p. 215 - 219

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-噻吩亚甲基)甲烷-1,1-二甲腈 在 copper(II) acetate monohydrate 作用下， 以 水 、 溶剂黄146 为溶剂， 以91%的产率得到β-(2-thienylmethylidene)(cyano)acetamide
  参考文献：
  名称：

  Homogeneous and Stereoselective Copper(II)-Catalyzed Monohydration of Methylenemalononitriles to 2-Cyanoacrylamides

  摘要：

  A facile and efficient route for the homogeneous and highly stereoselective monohydration of substituted methylenemalononitriles to (E)-2-cyanoacrylamides catalyzed by copper(II) acetate monohydrate in acetic acid containing 2% water is described, and a mechanism is proposed. The protocol has proved to be suitable for the monohydration of dicyanobenzenes and 2-substituted malononitriles.

  DOI：

  10.1021/jo401997v

文献信息

• An efficient catalyst-free one-pot synthesis of primary amides from the aldehydes of the Baylis–Hillman reaction
  作者：Thatikonda Narendar Reddy、Bikshapathi Raktani、Ramesh Perla、Mettu Ravinder、Jayathirtha Rao Vaidya、N. Jagadeesh Babu

  DOI：10.1039/c7nj01965c

  日期：——

  Herein, a facile and efficient method for the preparation of allyl amides from the aldehyde of Baylis–Hillman adducts has been developed using a hydroxylamine/methanol system under a catalyst-free condition. The effects of solvents and temperature on the reaction and substituents on the phenyl ring have been examined. This method is best demonstrated by its advantages such as operational simplicity

  在本文中，已经开发了一种在无催化剂条件下使用羟胺/甲醇系统从Baylis-Hillman加合物的醛制备烯丙基酰胺的简便有效的方法。研究了溶剂和温度对反应的影响以及苯环上的取代基。该方法的优点如操作简单，中等至极好的收率，较短的反应时间和简单的反应过程等得到了最好的证明。最重要的是，在没有催化剂和外部氧化剂的情况下，反应平稳进行。
• 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。
• Reaction of 3-aryl-2-cyanothioacrylamides with dimethyl acetylenecarboxylate, methyl propiolate, and N-phenylmaleimide
  作者：T. G. Deryabina、M. A. Demina、N. P. Belskaya、V. A. Bakulev

  DOI：10.1007/s11172-006-0204-4

  日期：2005.12

  The reaction of cyanothioacrylamides with dimethyl acetylenedicarboxylate, methyl propiolate, and N-phenylmaleimide was studied. The reaction follows a cycloaddition pathway to give thiopyrans, irrespective of the electronic or spatial effects of the substituents in the thioamide group and in position 3 of the 1-thiabuta-1,3-diene system. The reaction is regio-and stereoselective.

  研究了氰基硫代丙烯酰胺与乙炔二羧酸二甲酯、丙炔酸甲酯和 N-苯基马来酰亚胺的反应。无论硫代酰胺基团和 1-thiabuta-1,3-二烯系统的 3 位取代基的电子或空间效应如何，该反应都遵循环加成途径生成噻喃。该反应具有区域选择性和立体选择性。
• 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。
• 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.