3,5-bis(4-chlorophenyl)-4H-1,2,4-triazole | 56413-64-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-bis(4-chlorophenyl)-4H-1,2,4-triazole
• 英文别名: 3,5-bis-(4-chloro-phenyl)-1H-[1,2,4]triazole；3,5-Bis-(p-chlorphenyl)-4H-1,2,4-triazol；3,5-Di-(p-chlorophenyl)-1,2,4-triazol；3,5-Di-(p-Chlorophenyl)-s-triazol；1H-1,2,4-Triazole, 3,5-bis(4-chlorophenyl)-；3,5-bis(4-chlorophenyl)-1H-1,2,4-triazole
• CAS: 56413-64-0
• 化学式: C₁₄H₉Cl₂N₃
• 分子量: 290.152
• InChiKey: LWWUSHACMVZZSK-UHFFFAOYSA-N

物化性质

• 熔点：
  286-289 °C(Solv: isopropanol (67-63-0))
• 沸点：
  482.7±55.0 °C(Predicted)
• 密度：
  1.390±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲脒盐酸盐 在 铜 、 caesium carbonate 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 120.0 ℃ 、100.0 kPa 条件下， 反应 72.0h， 以60%的产率得到3,5-bis(4-chlorophenyl)-4H-1,2,4-triazole
  参考文献：
  名称：

  1,2,4-三唑的铜催化连续偶联和脒有氧氧化脱氢合成

  摘要：

  已经通过脒的反应开发了一种方便、有效和实用的铜催化一锅法合成 1,2,4-三唑。该过程通过两个脒之间的顺序碱基促进分子间偶联（亲核取代）和分子内有氧氧化脱氢，廉价、方便、高效的合成1,2,4-三唑的方法将受到学术界和工业界的广泛关注。研究。

  DOI：

  10.1055/s-0032-1317692

文献信息

• Copper-Catalyzed Synthesis of 1,2,4-Triazoles via Sequential Coupling and Aerobic Oxidative Dehydrogenation of Amidines
  作者：Hua Fu、Hao Xu、Yuyang Jiang

  DOI：10.1055/s-0032-1317692

  日期：——

  efficient, and practical copper-catalyzed one-pot method for the synthesis of 1,2,4-triazoles has been developed via reactions of amidines. The procedure underwent sequential base-promoted intermolecular coupling (nucleophilic substitution) between two amidines and intramolecular aerobic oxidative dehydrogenation, and the inexpensive, convenient, and efficient method for the synthesis of 1,2,4-triazoles

  已经通过脒的反应开发了一种方便、有效和实用的铜催化一锅法合成 1,2,4-三唑。该过程通过两个脒之间的顺序碱基促进分子间偶联（亲核取代）和分子内有氧氧化脱氢，廉价、方便、高效的合成1,2,4-三唑的方法将受到学术界和工业界的广泛关注。研究。
• An improved procedure for the deamination of symmetrical 3,5-disubstituted 4-amino-1,2,4-triazoles
  作者：Fouad Bentiss、Michel Lagrenee、Hervéa Vezin、Marya Bouanis、Bouchaib Mernari

  DOI：10.1002/jhet.5570390113

  日期：2002.1

  A number of symmetrical 3,5-disubstituted-4H-1,2,4-triazoles have been synthesized in good yields by deamination of the corresponding 4-amino-1,2,4-triazoles via reductive diazotation of these amino compounds in the presence of hypophosphorous acid. Analytical, spectral data and theoretical calculations confirmed the structures of the new triazole derivatives.

  通过将相应的4-氨基-1,2,4-三唑经氨基化合物的还原重氮化反应，将相应的4-氨基-1,2,4-三唑进行脱氨基反应，以高收率合成了许多对称的3,5-二取代-4 H -1,2,4-三唑。次磷酸的存在。分析，光谱数据和理论计算证实了新的三唑衍生物的结构。
• Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates
  作者：Kavitha Sudheendran、Dietmar Schmidt、Wolfgang Frey、Jürgen Conrad、Uwe Beifuss

  DOI：10.1016/j.tet.2014.01.019

  日期：2014.2

  Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)(2)-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K-3[Fe(CN)(6)]/atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4-triazoles with yields up to 64% rests on the Cu(OTf)(2)-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step. (C) 2014 Elsevier Ltd. All rights reserved.
• Copper-Mediated Sequential C–N and N–N Bond Formation: Facile Synthesis of Symmetrical 1,2,4-Triazoles
  作者：Zhiguo Zhang、Guisheng Zhang、Zhonglian Li、Wei Zhang、Qingfeng Liu、Tongxin Liu

  DOI：10.1055/s-0033-1338985

  日期：——

  Via a one-pot process, catalyzed by Cu(OAc)(2), a series of 3,5-disubstituted 4H-1,2,4-triazoles was conveniently and efficiently synthesized by using low-toxicity, stable, readily available, inexpensive amidine hydrochloride.
• Copper-Catalyzed One-Pot Synthesis of 1,2,4-Triazoles from Nitriles and Hydroxylamine
  作者：Hao Xu、Shuang Ma、Yuanqing Xu、Longxiang Bian、Tao Ding、Xiaomin Fang、Wenkai Zhang、Yanrong Ren

  DOI：10.1021/jo502709t

  日期：2015.2.6

  A simple and efficient copper-catalyzed one-pot synthesis of substituted 1,2,4-triazoles through reactions of two nitriles with hydroxylamine has been developed. The protocol uses simple and readily available nitriles and hydroxylamine hydrochloride as the starting materials and inexpensive Cu(OAc)(2) as the catalyst, and the corresponding 1,2,4-triazole derivatives are obtained in moderate to good yields. The reactions include sequential intermolecular addition of hydroxylamine to one nitrile to provide amidoxime, copper-catalyzed treatment of the amidoxime with another nitrile, and intramolecular dehydration/cyclization. This finding provides a new and useful strategy for synthesis of 1,2,4-triazole derivatives.

表征谱图