N-benzyl-2-cyano-3,3-bis(methylthio)acrylamide | 57280-06-5

• 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: N-benzyl-2-cyano-3,3-bis(methylthio)acrylamide
• 英文别名: N-Benzyl-2-cyano-3,3-bismethylthioacrylamid；N-benzyl-2-cyano-3,3-bis(methylsulfanyl)prop-2-enamide
• CAS: 57280-06-5
• 化学式: C₁₃H₁₄N₂OS₂
• 分子量: 278.399
• InChiKey: PHGDJVHOZTXSGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  74.2-75.8 °C
• 沸点：
  469.3±45.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-cyano-3,3-bis(methylthio)acrylamide 在 ammonium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-amino-N-benzyl-2-cyano-3-((2-methoxyphenyl)amino)acrylamide
  参考文献：
  名称：

  Karelia, Chirag; Parmar, Kailash; Teli, Divya, Journal of the Indian Chemical Society, 2020, vol. 97, # 8, p. 1227 - 1235

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基-N-(苯基甲基)-乙酰胺 在 potassium hydroxide 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 N-benzyl-2-cyano-3,3-bis(methylthio)acrylamide
  参考文献：
  名称：

  Synthesis and Antiviral Bioactivities of 2-Cyano-3-substituted-amino(phenyl) Methylphosphonylacrylates (Acrylamides) Containing Alkoxyethyl Moieties

  摘要：

  An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, H-1, C-13, and P-31 NMR spectral data. The role of introducing various substituents and the effect of incorporating alpha-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.

  DOI：

  10.1021/jf902861m

文献信息

• Synthesis and insecticidal activities of novel neonicotinoid analogs bearing an amide moiety
  作者：Jian Wu、Song Yang、Bao-An Song、Pinaki S. Bhadury、De-Yu Hu、Song Zeng、Hua-Peng Xie

  DOI：10.1002/jhet.663

  日期：2011.7

  A series of novel neonicotinoid analogs containing an amide moiety were synthesized, characterized, and subsequently evaluated for their insecticidal activity. According to the preliminary bioassay, the compounds 6c, 6e, 6f, 6j, 6n, and 6r exhibited > 50% activity against Nilaparvata lugens at 100 mg/L. Amongst the active compounds, 6f and 6r revealed insecticidal activities similar to that displayed

  合成，表征了一系列新颖的含有酰胺部分的新烟碱类似物，并随后对其杀虫活性进行了评估。根据初步的生物测定，化合物6c，6e，6f，6j，6n和6r在100 mg / L的浓度下对褐飞虱具有> 50％的活性。在活性化合物中，6f和6r的杀虫活性与标准丁苯丙酸所显示的相似。J.杂环化​​学。（2011）
• αα′-Dicyano-(1,3-dithiacyclobutane-2,4-diylidene)diacetamides (desaurins) from thiazine derivatives
  作者：Masataka Yokoyama

  DOI：10.1039/p19750001417

  日期：——

  The title compounds (1) were synthesized in good yields by refluxing N-alkyl-2-cyano-3-mercapto-3-methylthio-acrylamides (3) with acetic anhydride. Compounds (3) were prepared by a novel hydrogenolysis of 2,2-disubstituted 3,4-dihydro-6-methylthio-4-oxo-2H-1,3-thiazine-5-carbonitriles (2) with lithium aluminium hydride or sodium borohydride.

  通过使N-烷基-2-氰基-3-巯基-3-甲硫基丙烯酰胺（3）与乙酸酐回流，以高收率合成标题化合物（1）。化合物（3）是通过将2,2-二取代的3,4-二氢-6-甲硫基-4-氧代-2 H -1,3-噻嗪-5-腈（2）与氢化铝锂进行新型氢解反应制得的硼氢化钠。
• Synthesis and Antiviral Activities of Cyanoacrylate Derivatives Containing an α-Aminophosphonate Moiety
  作者：Ning Long、Xue-Jian Cai、Bao-An Song、Song Yang、Zhuo Chen、Pinaki S. Bhadury、De-Yu Hu、Lin-Hong Jin、Wei Xue

  DOI：10.1021/jf800405m

  日期：2008.7.1

  Target compounds 8 were obtained by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylate or cyarylamide (7a-7e) and (alpha-aminobenzylphosphonate (5a-5e) under reflux condition using ethanol as solvent. Their structures were clearly verified by spectroscopic data (IR and (1)H, (13)C, and (31)P NMR) and elemental analysis. These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 8d and 8e had the same inactivation effect against tobacco mosaic virus (EC(50) = 55.5 and 55.3 mu g/mL) as the commercial product ningnanmycin (EC(50) = 50.9 mu g/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of cyanoacrylate derivatives containing an alpha-aminophosphonate moiety.
• YOKOYAMA M., J. CHEM. SOC. PERKIN TRANS. PART I <JCPK-BH>, 1975, NO 14, 1417-1418
  作者：YOKOYAMA M.

  DOI：——

  日期：——
• Karelia, Chirag; Parmar, Kailash; Teli, Divya, Journal of the Indian Chemical Society, 2020, vol. 97, # 8, p. 1227 - 1235
  作者：Karelia, Chirag、Parmar, Kailash、Teli, Divya、Chhabria, Mahesh

  DOI：——

  日期：——