2-amino-4-propylthiophene-3-carbonitrile | 1326708-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-amino-4-propylthiophene-3-carbonitrile
• CAS: 1326708-44-4
• 化学式: C₈H₁₀N₂S
• 分子量: 166.247
• InChiKey: KEVMRUKHQUOFBB-UHFFFAOYSA-N

物化性质

• 沸点：
  308.3±42.0 °C(predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  正丁醛 、 丙二腈 在 Na₂S₆ 作用下， 以 水 为溶剂， 反应 0.83h， 以68%的产率得到2-amino-4-propylthiophene-3-carbonitrile
  参考文献：
  名称：

  First Gewald reaction ignited by sodium polysulfide: greener ultrasound-promoted synthesis of substituted 2-aminothiophenes in the absence of catalyst

  摘要：

  In this paper, a modified and facile Gewald reaction triggered by sodium polysulfide in the absence of catalytic base was developed. This approach involves a one-pot ultrasound-irritated aqueous reaction between ketones or aldehydes, malononitrile, and sodium polysulfide, which are converted into the corresponding 2-aminothiophene derivatives in moderate to high yields. In comparison with conventional methods, the prominent features of this sonocatalyzed procedure are experimental simplicity, good functional group tolerance, atom efficiency, and the use of water as a green solvent.[GRAPHICS].

  DOI：

  10.1080/17415993.2012.754892

文献信息

• Fungizide Verwendung von substituierten Thienylaminen
  申请人：BAYER AG

  公开号：EP0253259A2

  公开（公告）日：1988-01-20

  Verwendung von substituierten Thienylaminen der allgemei­nen Formel in welcher X  für Sauerstoff oder Schwefel steht, R¹ und R²  gleich oder verschieden sind und für Wasser­stoff, Halogen, Nitro, Cyano, Alkoxy, Alkylthio, Halogenalkoxy, Halogenalkylthio oder für gegebe­nenfalls substituierte Reste aus der Reihe Al­kyl, Aryl, Alkylcarbonyl oder Arylcarbonyl stehen, oder R¹ und R²  gemeinsam mit den angrenzenden beiden Kohlen­stoffatomen für einen gegebenenfalls durch Alkyl substituierten gesättigten oder ungesättigten carbocyclischen Ring stehen, R³  für Wasserstoff oder Alkyl steht und R⁴  für gegebenenfalls substituiertes Alkyl, für Cycloal­kyl, Alkenyl oder für gegebenenfalls substituiertes Aryl steht, als Fungizide im Pflanzenschutz.

  通式中 X 为氧或硫，R¹ 和 R² 相同或不同且为氢、卤素、硝基、氰基、烷氧基、烷硫基、卤代烷氧基、卤代烷硫基或由烷基、芳基、烷基羰基或芳基羰基组成的系列中的任选取代基，或 R¹ 和 R² 连同相邻的两个碳原子为任选被烷基取代的饱和或不饱和碳环，R³ 为氢或烷基，R⁴ 为任选取代的烷基、环烷基、烯基或任选取代的芳基的取代噻吩胺，作为植物保护中的杀菌剂。
• A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction
  作者：Xian-Gui Huang、Jia Liu、Jiangmeng Ren、Tao Wang、Weidong Chen、Bu-Bing Zeng

  DOI：10.1016/j.tet.2011.06.061

  日期：2011.8

  A simple and efficient procedure was developed for the synthesis of multisubstituted 2-aminothiophene derivatives. In the presence of catalytic amount of imidazole, ketones or aldehydes, dicyanomethane and elemental sulfur were converted into the corresponding 2-aminothiophene derivatives in moderate to high yields in DMF at 60 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.
• First Gewald reaction ignited by sodium polysulfide: greener ultrasound-promoted synthesis of substituted 2-aminothiophenes in the absence of catalyst
  作者：Chengyuan Liang、Dong Lei、Xiuzhen Wang、Qingqing Zhang、Qizheng Yao

  DOI：10.1080/17415993.2012.754892

  日期：2013.10.1

  In this paper, a modified and facile Gewald reaction triggered by sodium polysulfide in the absence of catalytic base was developed. This approach involves a one-pot ultrasound-irritated aqueous reaction between ketones or aldehydes, malononitrile, and sodium polysulfide, which are converted into the corresponding 2-aminothiophene derivatives in moderate to high yields. In comparison with conventional methods, the prominent features of this sonocatalyzed procedure are experimental simplicity, good functional group tolerance, atom efficiency, and the use of water as a green solvent.[GRAPHICS].