2-苯基-2H-1,2,3-三唑-4-甲酰氯 | 36386-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-苯基-2H-1,2,3-三唑-4-甲酰氯
• 英文名称: 2-phenyl-1,2,3-triazol-4-ylcarboxylic acid chloride
• 英文别名: 2-phenyl-1,2,3-triazole-4-carboxylic acid chloride；2-phenyl-2H-1,2,3-triazole-4-carbonyl chloride；2-phenyl-2H-[1,2,3]triazole-4-carbonyl chloride；2-phenyltriazole-4-carbonyl chloride
• CAS: 36386-85-3
• 化学式: C₉H₆ClN₃O
• 分子量: 207.619
• InChiKey: RVULOBVPCMOVMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-苯基-2H-1,2,3-三唑-4-甲酰氯 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-苯基-1,2,3-三唑-4-羧酸
  参考文献：
  名称：

  1,2,3-三唑与三氟甲磺酰氯和三氟甲磺酸酐的反应

  摘要：

  Reactions of 4,5-dibromo-1,2,3-triazole, 1H-1,2,3-benzotriazole, and 2-phenyl-2H-1,2,3-triazole-4-carbonyl chloride with trifluoromethanesulfonyl chloride and trifluoromethanesulfonic anhydride were studied. 4,5-Dibromo-1,2,3-triazole sodium salt reacted with CF3SO2Cl in tetrahydrofuran to give 4,5-dibromo-2-(2-tetrahydrofuryl)-2H-1,2,3-triazole rather than expected 4,5-dibromo-2-trifluoromethylsulfonyl-2H-1,2,3-triazole. The latter was synthesized by treatment of 4,5-dibromo-1,2,3-triazole sodium salt with trifluoromethanesulfonic anhydride. The reaction of benzotriazole with (CF3SO2)(2)O afforded 1-trifluoromethylsulfonyl-1H-1,2,3-benzotriazole and 1,2,3-benzotriazolium trifluoromethanesulfonate. 2-Phenyl-2H-1,2,3-triazole-4-carbonyl chloride reacted with trifluoromethanesulfonamide sodium salt in DMF, yielding N-(dimethylaminomethylene)trifluoromethanesulfonamide. Possible ways for formation of the unexpected products were proposed.

  DOI：

  10.1023/b:rujo.0000010573.40618.c0
• 作为产物：
  描述：

  2-苯基-1,2,3-三唑-4-羧酸 在 五氯化磷 作用下， 以 苯 为溶剂， 反应 2.0h， 以78%的产率得到2-苯基-2H-1,2,3-三唑-4-甲酰氯
  参考文献：
  名称：

  Synthesis of polynuclear azoles linked through carbamate and urea bridges

  摘要：

  Polynuclear azoles linked through carbamate and urea fragments were synthesized by reactions of the corresponding azolecarboxylic acid azides with heterocyclic alcohols and amines.

  DOI：

  10.1134/s1070428012040185

文献信息

• Synthesis of branched polynuclear 1,3,4-oxadiazoles
  作者：L. I. Vereshchagin、O. N. Verkhozina、A. G. Proidakov、A. I. Smirnov、V. N. Kizhnyaev

  DOI：10.1007/s10593-008-0163-9

  日期：2008.9

  The reaction of 5-substituted mono-and polytetrazoles with heterocyclic acid chlorides and trifluoroacetic acid anhydride gave branched polynuclear 1,3,4-oxadiazole systems.
• Some Further Studies of 2-Phenyl-1,2,3,2H-Triazole Derivatives
  作者：J. L. Riebsomer、D. A. Stauffer

  DOI：10.1021/jo50004a023

  日期：1951.10
• The curtius reaction in the synthesis of noncondensed polynuclear azoles
  作者：L. I. Vereshchagin、T. V. Golobokova、F. A. Pokatilov、A. G. Proidakov、O. N. Verkhozina、A. I. Smirnov、V. N. Kizhnyaev

  DOI：10.1007/s10593-011-0781-5

  日期：2011.7

  Polynuclear noncondensed systems in which the azole rings are bound by urethane or carbamide fragments have been synthesized by the reaction of azole carboxylic acid azides with heterocyclic alcohols.
• Swartz, David L.; Karash, Angela R.; Berry, Laura A., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1561 - 1564
  作者：Swartz, David L.、Karash, Angela R.、Berry, Laura A.、Jaeger, David L.

  DOI：——

  日期：——
• Human β3-adrenergic receptor agonists containing 1,2,3-triazole-substituted benzenesulfonamides
  作者：Linda L Brockunier、Emma R Parmee、Hyun O Ok、Mari R Candelore、Margaret A Cascieri、Lawrence F Colwell、Liping Deng、William P Feeney、Michael J Forrest、Gary J Hom、D.Euan MacIntyre、Laurie Tota、Matthew J Wyvratt、Michael H Fisher、Ann E Weber

  DOI：10.1016/s0960-894x(00)00422-4

  日期：2000.9

  Compounds containing a 1,2,3-triazole-substituted benzenesulfonamide were prepared and found to be potent and selective human beta(3)-adrenergic receptor agonists. The most interesting compound, trifluoromethylbenzyl analogue 12e (beta(3) EC50 = 3.1 nM with >1500-fold selectivity over binding to both beta(1)- and beta(2) receptors), stimulates lipolysis in the rhesus monkey (ED50 = 0.36 mg/kg) and is 25% orally bioavailable in the dog. (C) 2000 Elsevier Science Ltd. All rights reserved.