2-benzyl-2,4-dihydro-4-methyl-3H-1,2,4-triazole-3-thione | 81678-24-2

• 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: 2-benzyl-2,4-dihydro-4-methyl-3H-1,2,4-triazole-3-thione
• 英文别名: 2-benzyl-4-methyl-1,2,4-triazoline-3-thione；1-benzyl-4-methyl-1,2,4-triazoline-5-thione；2-Benzyl-4-methyl-1,2,4-triazole-3-thione
• CAS: 81678-24-2
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: IQNTWKMBOCUJSA-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  296.7±33.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苄基-1,2,4-噻唑 在 sodium sulfide 、 正丁基锂 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-benzyl-2,4-dihydro-4-methyl-3H-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Kawasaki, Ikuo; Domen, Akane; Kataoka, Shin-ya, Heterocycles, 2003, vol. 60, # 2, p. 351 - 363

  摘要：

  DOI：

文献信息

• Synthesis and Crystal Structures of New 1,4-Disubstituted 1,2,4-Triazoline-5-thiones
  作者：Gerhard Laus、Volker Kahlenberg、Klaus Wurst、Herwig Schottenberger

  DOI：10.5560/znb.2014-4145

  日期：2014.10.1

  Introduction of sulfur into the 5-position of 1,4-disubstituted quaternary 1,2,4-triazolium salts (1-9; Cl, Br, I, BF₄, PF₆, CH₃OSO₃ were used as anions) by two methods was investigated. The syntheses of nine 1,4-disubstituted 1,2,4-triazoline-5-thiones 10-18 are reported (1, 10: R¹ = CH₃, R² = CH₃; 2, 11: R¹ = NH₂, R² = CH₃; 3, 12: R¹ = NH₂, R² = CH(CH₃)₂; 4, 13: R¹ = N(CH₃)₂, R² = CH₃; 5, 14: R¹ = N(CH₃)₂, R² = CH(CH₃)₂; 6, 15: R¹ = CH₃, R² = NH₂; 7, 16: R¹ = OCH₂Ph, R² = CH₃; 8, 17: R¹ = OCH₂Ph, R² = CH₂CH₃; 9, 18: R¹ = CH₃, R² = CH₂Ph). Compounds 11-17 represent 1-amino, 4-amino, 4-dimethylamino, and 4-benzyloxy-1,2,4-triazoline-5- thiones, whereas 10 served as a reference compound. Thione 18 was identified as an unexpected by-product in the synthesis of 16 and was also prepared independently. Thermolysis of 10 in air gave 1,4-dimethyl-1,2,4-triazolium hydrogensulfate. Crystal structures of eight 1,4-disubstituted 1,2,4- triazoline-5-thiones were determined by single-crystal X-ray diffraction. Intermolecular hydrogen bonds (C-H···S, C-H···N, N-H···N, N-H···S) were observed in the solid state. The solvent-dependent ¹H NMR chemical shifts of signals of 10 and 13 were satisfactorily correlated with the Kamlet- Abboud-Taft π* and b parameters in ten solvents. From the lack of correlation with the a parameter and from the C=S bond length (average 1.67 Å) a significant contribution of a mesoionic imidazolium-2-thiolate resonance structure seems unlikely

  摘要 通过两种方法研究了在 1,4-二取代季态 1,2,4-三唑鎓盐 (1-9; Cl, Br, I, BF4, PF6, CH3OSO3 被用作阴离子) 的 5 位引入硫。报告了九种 1,4-二取代的 1,2,4-三唑啉-5-硫代化合物 10-18 的合成（1, 10：R1 = CH3，R2 = CH3；2, 11：R1 = NH2，R2 = CH3；3, 12：R1 = NH2，R2 = CH(CH3)2；4, 13：4，13：R1 = N（CH3）2，R2 = CH3；5，14：R1 = N（CH3）2，R2 = CH（CH3）2；6，15：R1 = CH3，R2 = NH2；7，16：R1 = OCH2Ph，R2 = CH3；8，17：R1 = OCH2Ph，R2 = CH2CH3；9，18：R1 = CH3，R2 = CH2Ph）。化合物 11-17 代表 1-氨基、4-氨基、4-二甲基氨基和 4-苄氧基-1,2,4-三唑啉-5-硫酮，而 10 则作为参比化合物。硫酮 18 是在合成 16 的过程中意外发现的副产品，也是独立制备的。10 在空气中热解得到 1,4-二甲基-1,2,4-三唑鎓氢硫酸盐。通过单晶 X 射线衍射测定了 8 种 1,4 二甲基-1,2,4-三唑啉-5-硫酮的晶体结构。在固态下观察到了分子间氢键（C-H--S、C-H--N、N-H--N、N-H--S）。在十种溶剂中，10 和 13 信号的溶剂依赖型 1H NMR 化学位移与 Kamlet- Abboud-Taft π* 和 b 参数的相关性令人满意。从与 a 参数缺乏相关性和 C=S 键长度（平均 1.67 Å）来看，介离子咪唑鎓-2-硫酸酯共振结构似乎不可能做出重大贡献。
• Iwasaki, Shigeo, Heterocycles, 1982, vol. 17, p. 125 - 138
  作者：Iwasaki, Shigeo

  DOI：——

  日期：——
• Kawasaki, Ikuo; Domen, Akane; Kataoka, Shin-ya, Heterocycles, 2003, vol. 60, # 2, p. 351 - 363
  作者：Kawasaki, Ikuo、Domen, Akane、Kataoka, Shin-ya、Yamauchi, Kazuya、Yamashita, Masayuki、Ohta, Shunsaku

  DOI：——

  日期：——