4H-1,2,4-三唑,4-(苯基甲氧基)- | 164260-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4H-1,2,4-三唑,4-(苯基甲氧基)-
• 英文名称: 4-benzyloxy-1,2,4-triazole
• 英文别名: 4-Phenylmethoxy-1,2,4-triazole
• CAS: 164260-87-1
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: XQEHLILQTHDAMM-UHFFFAOYSA-N

物化性质

• 沸点：
  319.4±35.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 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：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4H-1,2,4-三唑,4-(苯基甲氧基)- 在 氢溴酸 作用下， 反应 4.0h， 以99%的产率得到4-hydroxy-1,2,4-triazole hydrobromide
  参考文献：
  名称：

  Begtrup, Mikael; Vedso, Per, Journal of the Chemical Society. Perkin transactions I, 1995, # 3, p. 243 - 248

  摘要：

  DOI：
• 作为产物：
  描述：

  O-苄基羟胺 、 N,N-dimethylformamidazin dihydrochloride 以 吡啶 为溶剂， 反应 4.0h， 以42%的产率得到4H-1,2,4-三唑,4-(苯基甲氧基)-
  参考文献：
  名称：

  Synthesis, structure and electronic properties of N-dialkylamino- and N-alkoxy-1,2,4-triazol-3-ylidene ligands

  摘要：

  4-Amino- and 4-alkoxy-1,2,4-triazoles 4a-d and 6 were readily obtained from the reaction of N,N-dimethyiformamidazin dihydrochloride 3 with hydrazines 2 and hydroxylamine 5. Alkylation of compounds 4a-d and 6 by MeOTf or MeI afforded azolium salts 9-11, which in turn were transformed into Rh(l) carbene complexes 13-15, Ag carbenes 16, and cationic Rh(l) bis-carbenes 17. Additionally.. complexes 13 and 15 were transformed into dicarbonyl derivatives 18 and 19, and the carbonyl stretching frequencies of these compounds were used to evaluate the effect of the amino and alkoxy groups in the sigma-donor ability of these 1,2,4-triazol-3-ylidenes. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.07.120

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。
• Begtrup, Mikael; Vedso, Per, Journal of the Chemical Society. Perkin transactions I, 1995, # 3, p. 243 - 248
  作者：Begtrup, Mikael、Vedso, Per

  DOI：——

  日期：——
• Synthesis, structure and electronic properties of N-dialkylamino- and N-alkoxy-1,2,4-triazol-3-ylidene ligands
  作者：Manuel Alcarazo、Rosario Fernández、Eleuterio Álvarez、José M. Lassaletta

  DOI：10.1016/j.jorganchem.2005.07.120

  日期：2005.12

  4-Amino- and 4-alkoxy-1,2,4-triazoles 4a-d and 6 were readily obtained from the reaction of N,N-dimethyiformamidazin dihydrochloride 3 with hydrazines 2 and hydroxylamine 5. Alkylation of compounds 4a-d and 6 by MeOTf or MeI afforded azolium salts 9-11, which in turn were transformed into Rh(l) carbene complexes 13-15, Ag carbenes 16, and cationic Rh(l) bis-carbenes 17. Additionally.. complexes 13 and 15 were transformed into dicarbonyl derivatives 18 and 19, and the carbonyl stretching frequencies of these compounds were used to evaluate the effect of the amino and alkoxy groups in the sigma-donor ability of these 1,2,4-triazol-3-ylidenes. (c) 2005 Elsevier B.V. All rights reserved.