4-allyl-1-(thiophene-2-carbonyl)-thiosemicarbazide

• 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: 4-allyl-1-(thiophene-2-carbonyl)-thiosemicarbazide
• 英文别名: 4-Allyl-1-(thiophen-2-carbonyl)-thiosemicarbazid；N-allyl-2-(2-thienylcarbonyl)hydrazinecarbothioamide；1-prop-2-enyl-3-(thiophene-2-carbonylamino)thiourea
• 化学式: C₉H₁₁N₃OS₂
• mdl: MFCD03768403
• 分子量: 241.338
• InChiKey: DWAQZBVAVLMEHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-allyl-1-(thiophene-2-carbonyl)-thiosemicarbazide 在 乙醇 、 potassium hydroxide 作用下， 反应 3.0h， 以75%的产率得到4-烯丙基-5-噻吩-2-基-4H-1,2,4-噻唑-3-硫醇
  参考文献：
  名称：

  Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones

  摘要：

  A novel series of compounds were synthesized by cyclic condensation reaction of substituted isothiocyanate (2a-c) with 2-thiophenecarboxylic acid hydrazide (1) in the presence of ethyl alcohol, to obtain intermediate thiosemicarbazides (3a-c), which were further treated with sodium hydroxide in the presence of ethanol to obtain triazole derivatives (4a-c). The latter were refluxed with substituted secondary amines and formaldehyde for 6-10 h to afford Mannich bases (5a-k). The synthesized compounds were characterized on the basis of their spectral (IR, C-13 and H-1 NMR) data and evaluated for biological activities. Some of the compounds were found to exhibit significant antimicrobial and antioxidant activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.025
• 作为产物：
  描述：

  2-噻吩甲酰肼 、 天然芥菜籽油 在 乙醇 作用下， 生成 4-allyl-1-(thiophene-2-carbonyl)-thiosemicarbazide
  参考文献：
  名称：

  Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones

  摘要：

  A novel series of compounds were synthesized by cyclic condensation reaction of substituted isothiocyanate (2a-c) with 2-thiophenecarboxylic acid hydrazide (1) in the presence of ethyl alcohol, to obtain intermediate thiosemicarbazides (3a-c), which were further treated with sodium hydroxide in the presence of ethanol to obtain triazole derivatives (4a-c). The latter were refluxed with substituted secondary amines and formaldehyde for 6-10 h to afford Mannich bases (5a-k). The synthesized compounds were characterized on the basis of their spectral (IR, C-13 and H-1 NMR) data and evaluated for biological activities. Some of the compounds were found to exhibit significant antimicrobial and antioxidant activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.025

文献信息

• Facile Synthesis of Naphtho[2,3-<i>d</i>]thiazoles, Naphtho[2,3-<i>e</i>][1,3,4]thiadiazines and Bis(naphtho[2,3-<i>d</i>]thiazolyl)copper(II) Derivatives from Heteroylthiosemicarbazides
  作者：Alaa A. Hassan、Nasr K. Mohamed、Lamiaa E. Abd El-Haleem、Stefan Bräse、Martin Nieger

  DOI：10.1002/cjoc.201600195

  日期：2016.8

  A one step synthesis protocol for the conversion of heteroylthiosemicarbazides and 2,3‐dichloro‐1,4‐naphthoquinone to naphtho[2,3‐d]thiazoles, naphtho[2,3‐e][1,3,4]thiadiazines as well as bis(naphtho[2,3‐d]thiazolyl)copper(II) derivatives is described. The products were conclusively confirmed by single crystal X‐ray analyses. A mechanism for the formation of the products is presented.

  一步合成方案，用于将杂芳基硫代氨基脲和2,3-二氯-1,4-萘醌转化为萘并[2,3- d ]噻唑，萘并[2,3- e ] [1,3,4]噻二嗪以及双（萘[2,3- d ]噻唑基）铜（II）衍生物的描述。产品通过单晶X射线分析最终确认。提出了形成产物的机制。
• Chemotherapy of Experimental Tuberculosis. X. Heterocyclic Acyl Derivatives of Substituted Semicarbazides¹
  作者：Harry L. Yale、Kathryn A. Losee、Frances M. Perry、Jack Bernstein

  DOI：10.1021/ja01637a054

  日期：1954.4
• Synthesis of Some New Heteroylhydrazono-1,3-thiazolidin-4-ones
  作者：Alaa A. Hassan、Nasr K. Mohamed、Lamiaa E. Abd El-Haleem、Stefan Bräse、Martin Nieger

  DOI：10.1002/jhet.2240

  日期：2015.9

  A series of (Z)‐methyl‐2‐[(Z)‐3‐substituted‐4‐oxo‐2‐(2‐picolinoyl‐/thiophene‐2‐carbonyl)‐hydrazonothiazolidin‐5‐ylidene]acetates were synthesized by condensation N‐substituted‐(2‐picolinoyl‐, thiophene‐2‐carbonyl)hydrazinecarbothioamides with dimethylacetylenedicarboxylate. The structure of thiazolidin‐4‐one derivatives has been confirmed unambiguously by single crystal X‐ray crystallography.
• Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones
  作者：Metin Koparir、Cahit Orek、Akif Evren Parlak、Abdurrazak Söylemez、Pelin Koparir、Mustafa Karatepe、Sevgi Durna Dastan

  DOI：10.1016/j.ejmech.2013.02.025

  日期：2013.5

  A novel series of compounds were synthesized by cyclic condensation reaction of substituted isothiocyanate (2a-c) with 2-thiophenecarboxylic acid hydrazide (1) in the presence of ethyl alcohol, to obtain intermediate thiosemicarbazides (3a-c), which were further treated with sodium hydroxide in the presence of ethanol to obtain triazole derivatives (4a-c). The latter were refluxed with substituted secondary amines and formaldehyde for 6-10 h to afford Mannich bases (5a-k). The synthesized compounds were characterized on the basis of their spectral (IR, C-13 and H-1 NMR) data and evaluated for biological activities. Some of the compounds were found to exhibit significant antimicrobial and antioxidant activity. (C) 2013 Elsevier Masson SAS. All rights reserved.