4-烯丙基-5-噻吩-2-基-4H-1,2,4-噻唑-3-硫醇 | 187795-50-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-烯丙基-5-噻吩-2-基-4H-1,2,4-噻唑-3-硫醇
• 中文别名: 4-丙-2-烯基-5-噻吩-2-基-2H-1,2,4-三唑-3-硫酮；4-烯丙基-5-(2-噻吩)-2H-1,2,4-三唑-3-硫酮；4-烯丙基-5-噻吩-2-基-4H-1,2,4-三唑-3-硫醇
• 英文名称: 4-allyl-5-(2-thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
• 英文别名: 4-prop-2-enyl-3-thiophen-2-yl-1H-1,2,4-triazole-5-thione
• CAS: 187795-50-2
• 化学式: C₉H₉N₃S₂
• mdl: MFCD03032535
• 分子量: 223.323
• InChiKey: PKFGYLPKWBDFLD-UHFFFAOYSA-N

物化性质

• 沸点：
  309.8±44.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-烯丙基-5-噻吩-2-基-4H-1,2,4-噻唑-3-硫醇 、 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以66%的产率得到
  参考文献：
  名称：

  Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain

  摘要：

  报告了一种高效的方法，用于不对称合成侧链中含有呋喃基和噻吩基取代的三唑的 a-氨基酸。该策略依赖于 3,4,5-取代的 1,2,4-三唑与含有由脱氢氨基酸（脱氢丙氨酸和 (E + Z)- 脱氢氨基丁酸）和手性助剂（即 (S)-2-N- N,N,N-三唑）形成的希夫碱的手性 NiII 复合物的 C=C 键的迈克尔加成。即(S)-2-N-(N0-苄基)氨基二苯甲酮和(S)-2-N-(N0-2-氯苄基)氨基二苯甲酮。这些反应的非对映选择性良好。水解非对映异构体混合物金属络合物可得到对映异构体纯度高（ee> 98%）的 a-氨基酸。

  DOI：

  10.5560/znb.2014-3221
• 作为产物：
  描述：

  2-噻吩甲酰肼 在 乙醇 、 potassium hydroxide 作用下， 反应 3.0h， 生成 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

文献信息

• 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.
• Asymmetric Synthesis of Enantiomerically Enriched a-Amino Acids Containing 2-Furyl- and 2-Thienyl-1,2,4-triazoles in the Side-Chain
  作者：Ashot S. Saghyan、Hayarpi M. Simonyan、Satenik G. Petrosyan、Anna F. Mkrtchyan、Lilit V. Khachatryan、Arpine V. Geolchanyan、Melanya A. Samvelyan、Tariel V. Ghochikyan、Nazken Kelzhanova、Amanzhan T. Saginayev、Peter Langer

  DOI：10.5560/znb.2014-3221

  日期：2014.4.1

  An efficient method for the asymmetric synthesis of a-amino acids, containing furyl- and thiophenyl-substituted triazoles in their side-chain, is reported. The strategy relies on Michael addition of 3,4,5-substituted 1,2,4-triazoles to the C=C bond of chiral NiII complexes containing the Schiff base formed from dehydroamino acids (dehydroalanine and (E + Z)-dehydroaminobutyric acid) and from chiral auxiliaries, i. e. (S)-2-N-(N0-benzylprolyl)aminobenzophenone and (S)-2-N- (N0-2-chlorobenzylprolyl) aminobenzophenone. The reactions proceeded with good to very good diastereoselectivity. Hydrolysis of the diastereomeric mixtures of metal complexes afforded the enantiomerically pure a-amino acids with high enantiomeric excess (ee> 98%).

  报告了一种高效的方法，用于不对称合成侧链中含有呋喃基和噻吩基取代的三唑的 a-氨基酸。该策略依赖于 3,4,5-取代的 1,2,4-三唑与含有由脱氢氨基酸（脱氢丙氨酸和 (E + Z)- 脱氢氨基丁酸）和手性助剂（即 (S)-2-N- N,N,N-三唑）形成的希夫碱的手性 NiII 复合物的 C=C 键的迈克尔加成。即(S)-2-N-(N0-苄基)氨基二苯甲酮和(S)-2-N-(N0-2-氯苄基)氨基二苯甲酮。这些反应的非对映选择性良好。水解非对映异构体混合物金属络合物可得到对映异构体纯度高（ee> 98%）的 a-氨基酸。