1-(difluoromethyl)-5-phenyl-1H-tetrazole

• 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-(difluoromethyl)-5-phenyl-1H-tetrazole
• 英文别名: 1-N-Difluoromethyl-5-phenyltetrazole；1-(Difluoromethyl)-5-phenyltetrazole
• 化学式: C₈H₆F₂N₄
• 分子量: 196.159
• InChiKey: QCCILXZVELHLBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-苯基四氮唑 、 2-氯-2,2-二氟乙酸甲酯 在 potassium fluoride 、 18-冠醚-6 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 8.0h， 以5%的产率得到2-(difluoromethyl)-5-phenyl-2H-tetrazole
  参考文献：
  名称：

  N-difluoromethylation of phenylazoles

  摘要：

  In the presence of one equivalent of NaH, 2- and 4-phenylimidazole and 3-phenyl-1,2,4-triazole can be N-difluoromethylated with ClCF2H. The difluoromethylation of 5-phenyltetrazole requires two equivalents of NaH. A mechanism is proposed to account for these differences. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00262-0

文献信息

• Synthesis of<i>gem</i>-Difluorocyclopropa(e)nes and O<i>-</i>, S<i>-</i>, N<i>-</i>, and P-Difluoromethylated Compounds with TMSCF₂Br
  作者：Lingchun Li、Fei Wang、Chuanfa Ni、Jinbo Hu

  DOI：10.1002/anie.201306703

  日期：2013.11.18

  Two-in-one: Me3 SiCF2 Br is an efficient difluorocarbene source and is compatible with both neutral and aqueous basic conditions. Bromide-ion-initiated [2+1] cycloaddition with alkenes/alkynes and hydroxide ion promoted α-addition with (thio)phenols, (thio)alcohols, sulfinates, heterocyclic amines, and H-phosphine oxides give the corresponding gem-difluorinated compounds with broad functional-group tolerance.
• <i>N</i>-Tosyl-<i>S</i>-difluoromethyl-<i>S</i>-phenylsulfoximine: A New Difluoromethylation Reagent for S-, N-, and C-Nucleophiles
  作者：Wei Zhang、Fei Wang、Jinbo Hu

  DOI：10.1021/ol900567c

  日期：2009.5.21

  The first alpha-difluoromethyl sulfoximine compound, 2, was successfully prepared by using the copper(II)-catalyzed nitrene transfer reaction. Compound 2 was found to be a novel and efficient difluoromethylation reagent for transferring the CF2H group to S-, N-, and C-nucleophiles. Deuterium-labeling experiments suggest that a difluorocarbene mechanism is involved in the current difluoromethylation reactions.