1-benzyl-5-trifluoromethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester | 549072-24-4

• 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: 1-benzyl-5-trifluoromethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester
• 英文别名: 5-trifluoromethyl-1-benzyl-1H-1,2,3-triazole-4-carboxylic acid ethyl ester；ethyl 1-benzyl-5-trifluoromethyl-1,2,3-triazole-4-carboxylate；ethyl 1-benzyl-5-(trifluoromethyl)triazole-4-carboxylate；ethyl 1-benzyl-5-(trifluoromethyl)-1H-1,2,3-triazole-4-carboxylate；1-Benzyl-5-(trifluoromethyl)-1H-1,2,3-triazole-4-carboxylic acid ethyl ester
• CAS: 549072-24-4
• 化学式: C₁₃H₁₂F₃N₃O₂
• 分子量: 299.252
• InChiKey: NQFFBIZOIVLQQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-trifluoromethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 以88%的产率得到1-benzyl-5-trifluoromethyl-1,2,3-triazole-4-carboxylic acid
  参考文献：
  名称：

  采用重氮转移反应制备 1-烷基-5-三氟甲基-1,2,3-三唑-4-羧酸的便捷途径

  摘要：

  3-(烷基氨基)-4,4,4-三氟丁-2-烯酸乙酯在1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)存在下与甲磺酰叠氮化物反应得到乙基1-烷基-5-三氟甲基-1,2,3-三唑-4-羧酸盐产率良好。酯基的进一步水解得到多克规模的标题化合物。

  DOI：

  10.1002/ejoc.201300030
• 作为产物：
  描述：

  3-benzylamino-4,4,4-trifluorobut-2-enoic acid ethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以76%的产率得到1-benzyl-5-trifluoromethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  采用重氮转移反应制备 1-烷基-5-三氟甲基-1,2,3-三唑-4-羧酸的便捷途径

  摘要：

  3-(烷基氨基)-4,4,4-三氟丁-2-烯酸乙酯在1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)存在下与甲磺酰叠氮化物反应得到乙基1-烷基-5-三氟甲基-1,2,3-三唑-4-羧酸盐产率良好。酯基的进一步水解得到多克规模的标题化合物。

  DOI：

  10.1002/ejoc.201300030

文献信息

• Monoacylglycerol Lipase Modulators
  申请人：Janssen Pharmaceutica NV

  公开号：US20200102311A1

  公开（公告）日：2020-04-02

  Bridged compounds of Formula (I) and Formula (II), pharmaceutical compositions containing them, methods of making them, and methods of using them including methods for treating disease states, disorders, and conditions associated with MGL modulation, such as those associated with pain, psychiatric disorders, neurological disorders (including, but not limited to major depressive disorder, treatment resistant depression, anxious depression, bipolar disorder), cancers and eye conditions. wherein R 2 , R 3 R 4 , R 5 and R 6 are defined herein.

  桥接化合物，其结构式为(I)和(II)，包含它们的药物组合物，制造它们的方法，以及使用它们的方法，包括用于治疗与MGL调节相关的疾病状态、障碍和状况的方法，如与疼痛、精神障碍、神经障碍（包括但不限于重性抑郁障碍、难治性抑郁、焦虑性抑郁、双相情感障碍）、癌症和眼科疾病相关的方法。 其中R2、R3、R4、R5和R6的定义如下。
• Efficient Synthesis of 5-Fluoroalkylated 1<i>H</i>-1,2,3-Triazoles and Application of the Bromodifluoromethylated Triazole to Prepare New<i>gem</i>-Difluorinated Triazole Compounds
  作者：Shizheng Zhu、Weimin Peng

  DOI：10.1055/s-2003-36784

  日期：——

  A series of 5-fluoroalkylated 1H-1,2,3-triazoles was prepared in good yield by the regiospecific 1,3-dipolar cycloaddition reaction of the (Z) ethyl 3-fluoroalkyl-3-pyrrolidino-acrylates with aryl or benzyl azides. In the cases of benzyl azides, addition of Na2CO3 was crucial for a high yield of the triazoles. The tetrakis(dimethylamino)ethylene (TDAE) promoted reaction of the bromo-difluoromethylated 1H-1,2,3-triazole with aldehyde afforded a new class of novel gem-difluorinated triazole compounds.

  通过 3-氟烷基-3-吡咯烷丙烯酸（Z）乙酯与芳基或苄基叠氮化物的 1,3-二极环加成反应，制备了一系列 5-氟烷基化的 1H-1,2,3-三唑，收率很高。在苄基叠氮化物的情况下，加入 Na2CO3 是获得高产率三唑的关键。在四(二甲基氨基)乙烯（TDAE）的促进下，溴二氟甲基化的 1H-1,2,3-三唑与醛发生反应，生成了一类新型的宝石二氟化三唑化合物。
• Trimethylsilyl-Directed 1,3-Dipolar Cycloaddition Reactions in the Solid-Phase Synthesis of 1,2,3-Triazoles
  作者：Steven J. Coats、Jeffrey S. Link、Diane Gauthier、Dennis J. Hlasta

  DOI：10.1021/ol047637y

  日期：2005.4.14

  [GRAPHICS]A regioselective method for the preparation of 1,5-trisubstituted H-1-1,2,3-triazoles via a 1,3-dipolar cycloaddition of 1-trimethylsilylacetylenes with organciazides is described. Immobilization of the azide on REM resin and subsequent cycloaddition afforded a 2 x 2 x 4 x 3 membered 1,5-disubstituted H-1-1,2,3-triazole library with an average purified yield of 68%.
• WO2008/75955
  申请人：——

  公开号：——

  公开（公告）日：——
• Efficient synthesis of 5-fluoroalkylated 1H-1,2,3-triazoles and application of the bromodifluoromethylated triazole to the synthesis of novel bicyclic gem-difluorinated 1H-pyrano[3,4-d][1,2,3]-triazol-4-one compounds
  作者：Weimin Peng、Shizheng Zhu

  DOI：10.1016/s0040-4020(03)00621-5

  日期：2003.6

  A series of 5-fluoroalkylated 1H-1,2,3-triazoles were synthesized in good yield by the regiospecific 1,3-dipolar cycloaddition reaction of (Z)-ethyl 3-fluoroalkyl-3-pyrrolidino-acrylates with aryl or benzyl azides. In the cases of benzyl azides, addition of Na2CO3 was crucial for a high yield of the triazoles. Tetrakis(dimethylamino)ethylene (TDAE) promoted reaction of bromodifluoro-methylated triazole with aldehydes affording a new class of beta,beta-difluoro-beta-triazolyl alcohol derivatives, which were lactonized with catalytic amount of p-toluenesulfonic acid in toluene at 80-90degreesC to give a series of novel bicyclic gem-difluorinated 1H-pyrano[3,4-d][1,2,3]-triazol-4-one compounds in good yield. (C) 2003 Elsevier Science Ltd. All rights reserved.