2-cyano-3-(4-dimethylaminophenyl)prop-2-enethioamide

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyano-3-(4-dimethylaminophenyl)prop-2-enethioamide
• 英文别名: 2-Cyano-3-(4-dimethylaminophenyl)thioacrylamide；2-cyano-3-[4-(dimethylamino)phenyl]prop-2-enethioamide
• 化学式: C₁₂H₁₃N₃S
• mdl: MFCD00449800
• 分子量: 231.321
• InChiKey: RYCMWLHJBKLTHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  85.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyano-3-(4-dimethylaminophenyl)prop-2-enethioamide 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  氰硫乙酰胺及其衍生物在杂环合成中的应用：几种新吡啶、吡唑并[3,4-b]吡啶、噻吩并[2,3-b]吡啶、[3,4-b]吡啶和[4-吡啶'5]的合成和表征,2′-d′]嘧啶衍生物

  摘要：

  摘要 吡啶硫酮衍生物 5a、b 因其含有一个以上的活性位点而被用作反应性起始材料。它与几种含卤素的物质反应得到相应的 2-S-烷基-或 2-S-芳基衍生物，然后环化为相应的噻吩并吡啶衍生物。所得噻吩并吡啶衍生物可通过与甲酸、亚硝酸、二硫化碳或乙酸酐反应来构建新环。

  DOI：

  10.1080/10426509908037010
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 ((4-(二甲基氨基)苯基)亚甲基)甲烷-1,1-二甲腈 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 反应 29.0h， 以78%的产率得到2-cyano-3-(4-dimethylaminophenyl)prop-2-enethioamide
  参考文献：
  名称：

  Synthesis of 4-methylmorpholinium 6-amino-3,5-dicyano-4-(furan-2-yl)pyridine-2-thio(seleno)lates and 3-[aryl(hetaryl)]-2-cyanoprop-2-enethioamides by michael reaction

  摘要：

  DOI：

  10.1134/s1070428014120185

文献信息

• 2-CYANOETHANETHIOAMIDE IN HETEROCYCLIC SYNTHESIS: NOVEL SYNTHESIS OF THIENO[2,3-B]PYRIDINE, PYRAZOLO[3,4-B]PYRIDINE AND PYRIDOPYRAZOLO- 1,2,4-TRIAZINE DERIVATIVES
  作者：Mohamed A.A. Elneairyi、Azza M. Abdel-fattah

  DOI：10.1080/10426500108040253

  日期：2001.8

  Abstract Several new synthesis of thieno[2.3-blpyridine, pyrazolo[3,4-b[pyridine and pyridopyrazolo-1,2,4-triazine derivatives via the reactions of pyridinethiones with halogenated compounds, hydrazine hydrate and active methylene compounds.

  摘要 通过吡啶硫酮与卤代化合物、水合肼和活性亚甲基化合物反应合成噻吩并[2.3-b-吡啶、吡唑并[3,4-b[吡啶和吡啶并吡唑并-1,2,4-三嗪]衍生物。
• α,β-Unsaturated Nitriles in Heterocyclic Synthesis. Novel Synthesis of Pyridines and Thieno[2,3-<i>b</i>]pyridine Derivatives
  作者：Galal E. H. Elgemeie、Hassan A. Elfahham、Hesham A. Nabey

  DOI：10.1246/bcsj.61.4431

  日期：1988.12

  reacts with ethyl acetoacetate and acetylacetone to give the corresponding 3-cyano-2(1H)-pyridinethione derivatives, which can be alkylated at sulfur atom and cyclized into the corresponding thieno[2,3-b]pyridine derivatives.

  芳基亚甲基氰硫代乙酰胺与乙酰乙酸乙酯和乙酰丙酮反应生成相应的 3-氰基-2(1H)-吡啶硫酮衍生物，该衍生物可在硫原子上烷基化并环化为相应的噻吩并[2,3-b]吡啶衍生物。
• 3-Aryl-2-(thiazol-2-yl)acrylonitriles assembled with aryl/hetaryl rings: Design of the optical properties and application prospects
  作者：Alexander K. Eltyshev、Timur H. Dzhumaniyazov、Polina O. Suntsova、Artem S. Minin、Varvara A. Pozdina、Wim Dehaen、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1016/j.dyepig.2020.108836

  日期：2021.1

  New fluorescent thiazoles were designed and synthesized based on a 3-aryl-2-(thiazol-2-yl)acrylonitrile core. Three synthetic approaches were developed to introduce specific combinations of substituents at the 2-, 4- and 5-thiazole positions. The obtained thiazolyl-2-acrylonitriles exhibited a wide range of fluorescent colours (from green to red), long wavelength maxima and intensity depending on the combination of the substituents located at rings A, B and C. The expanded photophysical investigation established the best substituent combinations to increase their emission. Absorption and emission were studied in solvents with different polarities, as well as in DMSO-water and dioxane-water mixtures. The thiazoles showed multifunctional properties and exhibited good emission in the solid phase and in suspension (aggregation induced enhancement emission/AIEE effect). Photophysical investigations revealed a large Stokes shift, significant positive solvatochmmism, and the tunability of the colour and intensity. Sharp strengthening of the emission intensity of the thiazoles was observed upon stimulation with some acid (H2SO4 and BF3 center dot OEt2) in solvents and in the solid phase (HCl). State-of-the-art quantum mechanical calculations were performed to interpret the experimental findings. Biological experiments revealed the good penetration of the thiazoles into living cells and the accumulation both in lysosomes and, to a lesser extent, near membranes.
• Synthesis of 3-cyano-4-aryl-5-ethoxycarbonyl-6-methyl-3,4-dihydropyridine-2-thiones
  作者：A. A. Krauze、�. �. Liepin'sh、Yu. �. Pelcher、Z. A. Kalme、I. V. Dipan、G. Ya. Dubur

  DOI：10.1007/bf00505906

  日期：1985.1
• Ghabrial, Sami S.; Zaki, Mayasoune Y., Journal of Chemical Research, Miniprint, 1997, # 7, p. 1560 - 1575
  作者：Ghabrial, Sami S.、Zaki, Mayasoune Y.

  DOI：——

  日期：——