1-decyl-1,2,4-triazole | 111371-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-decyl-1,2,4-triazole
• CAS: 111371-18-7
• 化学式: C₁₂H₂₃N₃
• 分子量: 209.335
• InChiKey: DCXWTPIPWSKJPM-UHFFFAOYSA-N

物化性质

• 沸点：
  321.9±25.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-decyl-1,2,4-triazole 以 水 为溶剂， 反应 8.0h， 生成 1-decyl-4-(3,3,3-trifluoropropyl)-1,2,4-triazolium bis(trifluoromethanesulfonyl)amide
  参考文献：
  名称：

  New Quaternary Polyfluoroalkyl-1,2,4-Triazolium Salts Leading to Ionic Liquids

  摘要：

  在 100-120 °C 的纯净反应条件下，使用多氟烷基卤化物在 N-4 处对 1-烷基-1,2,4-三唑进行季铵化反应，生成 1-R-4-Rf 三唑（Taz）卤化物，分离收率大于 98%。这些多氟烷基化的三唑鎓卤化物与含氟阴离子发生 Metathesis 反应，生成了新的离子液体 [R(Rf)Taz]+Y-。

  DOI：

  10.1055/s-2003-36254
• 作为产物：
  描述：

  1H-1,2,4-三唑 、 癸基溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以74%的产率得到1-decyl-1,2,4-triazole
  参考文献：
  名称：

  双噻唑鎓，双咪唑鎓和双三唑鎓衍生物的合成和抗菌评估

  摘要：

  鉴于细菌耐药性在世界范围内的传播，迫切需要开发具有有效抗菌活性且不受该现象影响的新化合物。季铵化合物已被用作消毒剂多年，但是最近的进展表明，与通常使用的单阳离子化合物相比，聚阳离子衍生物具有更强的活性，并且不易产生细菌耐药性。从这个意义上讲，我们制备了三套新的双阳离子化合物：双噻唑鎓，双咪唑鎓和双1,2,4-三唑鎓。如果第一个系列的某些化合物显示出良好的抗菌活性，则其他两个系列的大多数化合物都具有很高的效力，最低抑菌浓度接近1μgmL -1。它们中的一些对真核MRC-5肺成纤维细胞的毒性也很低，我们证明了这种毒性与Clog P明显相关。最后，发现四种选定的化合物表现出明显的杀菌作用。

  DOI：

  10.1002/cmdc.201900151

文献信息

• Synthesis and Sorption Analysis of Task-specific Fluorous Ionic Liquids
  作者：Verena Adamer、Gerhard Laus、Ulrich J. Griesser、Herwig Schottenberger

  DOI：10.5560/znb.2013-3142

  日期：2013.10.1

  Six 1-alkyl-4-tridecafluorooctyl-1,2,4-triazolium triflimides 2a-f and 4-amino-1-tridecafluorooctyl- 1,2,4-triazolium triflimide (4) were prepared from the respective iodides 1a-f (1a, 2a: n-propyl; 1b, 2b: n-butyl; 1c, 2c: n-hexyl; 1d, 2d: n-heptyl; 1e, 2e: n-octyl; 1f, 2f: n-decyl) and iodide 3 by ion metathesis. Compounds 2a and 4 are liquid at room temperature. Two liquid fluorous imidazolium salts bearing functionalized polar substituents were synthesized in an analogous manner, namely 1-(2- (diethylamino)ethyl)-3-(heptadecafluorodecyl)imidazolium triflimide (5b) and 1-(2-hydroxyethyl)- 3-(heptadecafluorodecyl)imidazolium triflimide (6b) from the respective bromides 5a and 6a. The bis(triflimide) 5c has a melting point slightly above room temperature. Three fluorous ionic liquids (ILs; 2a, 5b, and 6b) were subjected to vapor sorption analysis at 25 °C and exhibited dual affinity to water and, even much more pronounced, to methoxynonafluorobutane (hydrofluoroether HFE-7100). Thus, IL 6b absorbed 3:2% (by weight) water and 200% HFE, whereas ILs 2a and 5b absorbed 0.4 and 0:5% water, but 300 and 1200% HFE, respectively. Commercial 1-butyl-2,3- dimethyl-imidazolium triflimide and 1-ethyl-3-methyl-imidazolium triflimide were used as reference compounds and absorbed 0.9 and 2:2% water, respectively, but only 17% HFE.

  由各自的碘化物 1a-f 制备了六种 1-烷基-4-十三氟辛基-1,2,4-三唑三亚胺 2a-f 和 4-氨基-1-十三氟辛基-1,2,4-三唑三亚胺（4）（1a, 2a：1a，2a：正丙基；1b，2b：正丁基；1c，2c：正己基；1d，2d：正庚基；1e，2e：正辛基；1f，2f：正癸基）和碘化物 3 通过离子复分解反应制备而成。化合物 2a 和 4 在室温下呈液态。以类似的方法合成了两种带有官能化极性取代基的液态氟咪唑鎓盐，即 1-(2-(二乙基氨基)乙基)-3-(十七氟癸基)咪唑鎓三氟化物 (5b) 和 1-(2-羟乙基)-3-(十七氟癸基)咪唑鎓三氟化物 (6b)，它们分别来自各自的溴化物 5a 和 6a。双三亚胺 5c 的熔点略高于室温。对三种氟离子液体（ILs；2a、5b 和 6b）在 25 °C 下进行了蒸汽吸附分析，结果表明它们对水具有双重亲和力，对甲氧基壬基氟丁烷（氢氟醚 HFE-7100）的亲和力更为明显。因此，IL 6b 可吸收 3:2%（重量比）的水和 200% 的氢氟醚，而 IL 2a 和 5b 则分别可吸收 0.4% 和 0:5% 的水，但氢氟醚的吸收率分别为 300% 和 1200%。商用 1-丁基-2,3-二甲基-咪唑三氟利昂和 1-乙基-3-甲基-咪唑三氟利昂被用作参考化合物，它们分别吸收了 0.9% 和 2:2% 的水，但只吸收了 17% 的 HFE。
• Syntheses of 1-Alkyl-1,2,4-triazoles and the Formation of Quaternary 1-Alkyl-4-polyfluoroalkyl-1,2,4-triazolium Salts Leading to Ionic Liquids
  作者：Yousef R. Mirzaei、Brendan Twamley、Jean'ne M. Shreeve

  DOI：10.1021/jo026350g

  日期：2002.12.1

  1,2,4-Triazole was alkylated (alkyl = methyl, butyl, heptyl, decyl) at N-1 in > 90% isolated yields. The resulting 1-alkyl triazoles were quaternized at N-4 in > 98% isolated yields using fluorinated alkyl halides with > 98% isolated yields, under neat reaction conditions at 100-120 degreesC to form N1-CH2-N4-(CH2)(2)CmF2m (divided by 1)-triazolium (Taz) iodide (m = 1, 6), N1-C4H9-N4-(CH2)(2)CmF2m (+ 1)-Taz iodide (m = 1, 4, 6), N1-C7H15-N4-(CH2)(2)CmF2m + 1-Taz iodide (m = 1, 4, 6), NI-C10H21-N4-(CH2)(2)CmF2m (+ 1)-Taz iodide (m = 1, 4), and N1-CnH2n (divided by 1)-N4-(CH2)(2)F-Taz bromide (n = 4, 7, 10). Single-crystal X-ray analyses confirmed the structure of [1-CH3-4-CH2CH2CF3-Taz]I-+(-). It crystallized in the orthorhombic space group Pccn, and the unit cell dimensions were a = 13.8289(9) Angstrom, b = 17.3603-(11) Angstrom, c = 9.0587(6) Angstrom (alpha = beta = gamma = 90degrees). Metathesis of these polyfluoroalkyl-substituted triazolium halides with other salts led to the formation of quaternary compounds, some of which comprise ionic liquids, namely, [R(R-f)-Taz]Y-divided by(-) (Y = NTf2, BF4, PF6, and OTf), in good isolated yields without the need for further purification: N1-CH3-N4-(CH2)(2)CmF2m (+) (1)-Taz Y (m = 1, 6; Y = NTf2), N1-C4H9-N4-(CH2)(2)CmF2m (divided by) (1)-Taz Y (m = 1, 4, 6; Y = NTf2), N1-C7H15-N4-(CH2)(2)CmF2m (+ 1)-Taz Y (m = 1, 4, 6; Y = NTf2), N1-C10H21-N4-(CH2)(2)CmF2m (+ 1)-Taz Y (n = 1, 4; Y = NTf2), N1-CnH2n (+ 1)-N4-(CH2)(2)F-Taz Y (n = 7, 10; Y = NTf2), N1-C10H21-N4-(CH2)(2)F-TazY (Y = OTf), N1-C7H15-N4-(CH2)(2)F-TazY (Y = BF4), N1-C4H9-N4-(CH2)(2)C(m)F2(m) (+ 1)-Taz Y (m 4, 6; Y PF6) N1-C7H15-N4-(CH2)(2)C4F9-Taz Y (Y = PF6) N1-C4H9-N4-(CH2)(2)C(m)F2(m) (+ 1)-Taz Y (m 4, 6; Y = OTf). All new compounds were characterized by H-1, F-19, and C-13 NMR and MS spectra and elemental analyses. T(g)s and T(m)s of ionic liquids were determined by DSC.
• Physicochemical and Thermal Properties for a Series of 1-Alkyl-4-methyl-1,2,4-triazolium Bis(trifluoromethylsulfonyl)imide Ionic Liquids
  作者：Andreah T. De La Hoz、Ulises G. Brauer、Kevin M. Miller

  DOI：10.1021/jp505592t

  日期：2014.8.21

  Physicochemical properties and long-term thermal stabilities are reported for a series of 1-alkyl-4-methyl-1,2,4-triazolium [NTf2] ionic liquids, and a Walden plot analysis was conducted in order to determine the ionicity of these materials. In general, viscosities were found to increase with increasing alkyl chain length while densities and molar conductivities were found to decrease. The 1,2,4-triazolium ionic liquids were classified as "good" ionic liquids after analysis of the Walden plot; however, they did not perform as well as the standard imidazolium ionic liquid [bmim][NTf2]. Thermal properties from DSC and TGA experiments were also completed. 1,2,4-Triazolium ionic liquids with an alkyl chain length of octyl (C8) or less exhibited a single Tg transition below -70 °C; however, the decyl (C10) and dodecyl (C12) systems exhibited a Tm value. No correlation between Tonset or Td5% and alkyl chain length was observed during short-term, temperature-ramped TGA experiments. However, long-term, isothermal TGA studies indicated a general increase in T0.01/10 value as the alkyl chain length increased. Both short- and long-term TGA studies indicated that the 1,2,4-triazolium ionic liquids were not as thermally stable as the model imidazolium ionic liquid [bmim][NTf2].
• US4220764A
  申请人：——

  公开号：US4220764A

  公开（公告）日：1980-09-02
• Synthesis and Antibacterial Evaluation of Bis‐thiazolium, Bis‐imidazolium, and Bis‐triazolium Derivatives
  作者：Benoît Thomas、Raphaël E. Duval、Stéphane Fontanay、Mihayl Varbanov、Michel Boisbrun

  DOI：10.1002/cmdc.201900151

  日期：2019.7.3

  compounds: bis‐thiazoliums, bis‐imidazoliums, and bis‐1,2,4‐triazoliums. If some compounds of the first series showed fair antibacterial activity, most of those belonging to the two other series were highly potent, with minimum inhibitory concentrations close to 1 μg mL−1. Some of them also exhibited low toxicity toward eukaryotic MRC‐5 lung fibroblasts, and we showed that this toxicity is clearly correlated

  鉴于细菌耐药性在世界范围内的传播，迫切需要开发具有有效抗菌活性且不受该现象影响的新化合物。季铵化合物已被用作消毒剂多年，但是最近的进展表明，与通常使用的单阳离子化合物相比，聚阳离子衍生物具有更强的活性，并且不易产生细菌耐药性。从这个意义上讲，我们制备了三套新的双阳离子化合物：双噻唑鎓，双咪唑鎓和双1,2,4-三唑鎓。如果第一个系列的某些化合物显示出良好的抗菌活性，则其他两个系列的大多数化合物都具有很高的效力，最低抑菌浓度接近1μgmL -1。它们中的一些对真核MRC-5肺成纤维细胞的毒性也很低，我们证明了这种毒性与Clog P明显相关。最后，发现四种选定的化合物表现出明显的杀菌作用。