(2-(4-fluorophenyl)-2H-tetrazol-5-yl)methanol | 1202942-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2-(4-fluorophenyl)-2H-tetrazol-5-yl)methanol
• 英文别名: [2-(4-fluorophenyl)-2H-tetraazol-5-yl]methanol；[2-(4-Fluorophenyl)tetrazol-5-yl]methanol
• CAS: 1202942-52-6
• 化学式: C₈H₇FN₄O
• 分子量: 194.168
• InChiKey: LAKIQOBUQUITMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  63.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-(4-fluorophenyl)-2H-tetrazol-5-yl)methanol 在 三溴化磷 作用下， 以 乙醚 为溶剂， 以28%的产率得到5-(bromomethyl)-2-(4-fluorophenyl)-2H-tetraazole
  参考文献：
  名称：

  Synthesis and Structure−activity Relationships of Antitubercular 2-Nitroimidazooxazines Bearing Heterocyclic Side Chains

  摘要：

  Recently described biphenyl analogues Of the antituberculosis drug PA-824 displayed improved potencies against M. tuberculosis but were poorly soluble. Heterobiaryl analogues of these, in which the first phenyl ring was replaced with various 5-membered ring heterocycles, were prepared with the aim of identifying potent new candidates with improved aqueous solubility. The compounds were constructed by coupling the chiral 2-nitroimidazooxazine alcohol with various halomethyl-substituted arylheterocycles, by cycloadditions to a propargyl ether derivative of this alcohol, or by Suzuki couplings on haloheterocyclic methyl ether derivatives. The arylheterocyclic compounds were all more hydrophilic than their corresponding biphenyl analogues, and several showed solubility improvements. 1-Methylpyrazole, 1,3-linked-pyrazole, 2,4-linked-triazole, and tetrazole analogues had 3- to 7-fold higher MIC potencies against replicating M. tb than predicted by their lipophilicities. Two pyrazole analogues were >10-fold more efficacious than the parent drug in a mouse model of acute M. tb infection, and one displayed a 2-fold higher solubility.

  DOI：

  10.1021/jm901378u
• 作为产物：
  描述：

  4-fluorobenzenediazonium tetrafluoroborate 在 silver(I) acetate 、 二异丁基氢化铝 、 sodium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.17h， 生成 (2-(4-fluorophenyl)-2H-tetrazol-5-yl)methanol
  参考文献：
  名称：

  Regioselective synthesis of carboxylic and fluoromethyl tetrazoles enabled by silver-catalyzed cycloaddition of diazoacetates and aryl diazonium salts

  摘要：

  Here we present a dipolar [3 + 2] cycloaddition transformation of diazoacetates with arenediazonium salts under silver catalysis, thus offering a straightforward approach for the regioselective construction of carboxylic tetrazoles. Several merits are accompanied with this reaction including readily available starting reagents, broad coupling scope, high yields, and friendly reaction conditions. The synthetic value is further showcased by one-pot conversion of commercially available primary arylamines to tetrazoles and successful transformations of the cycloadducts into valuable 5-fluoromethyltetrazoles and an analogue of P2X3 receptor antagonist. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131063