5-(1,1-difluoro-2-hydroxy-2-phenylethyl)-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid ethyl ester | 549072-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(1,1-difluoro-2-hydroxy-2-phenylethyl)-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid ethyl ester
• 英文别名: 5-(1,1-difluoro-2-hydroxy-2-phenyl-ethyl)-1-phenyl-1-1H-1,2,3-triazole-4-carboxylic acid ethyl ester；Ethyl 5-(1,1-difluoro-2-hydroxy-2-phenylethyl)-1-phenyltriazole-4-carboxylate
• CAS: 549072-35-7
• 化学式: C₁₉H₁₇F₂N₃O₃
• 分子量: 373.359
• InChiKey: SVTAFGNPAUGKRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(1,1-difluoro-2-hydroxy-2-phenylethyl)-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid ethyl ester 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以68%的产率得到7,7-difluoro-1,6-diphenyl-6,7-dihydro-1H-pyrano[3,4-d][1,2,3]-triazol-4-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(03)00621-5
• 作为产物：
  描述：

  (Z) ethyl 3-bromodifluoromethyl-3-pyrrolidino-acrylate 在 四(二甲氨基)乙烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 90.0h， 生成 5-(1,1-difluoro-2-hydroxy-2-phenylethyl)-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Efficient Synthesis of 5-Fluoroalkylated 1H-1,2,3-Triazoles and Application of the Bromodifluoromethylated Triazole to Prepare Newgem-Difluorinated Triazole Compounds

  摘要：

  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。

  DOI：

  10.1055/s-2003-36784

文献信息

• 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。
• 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.