1,4-dihydro-1-(2-hydroxethyl)-4-phenyl-5H-tetrazol-5-one | 35727-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-dihydro-1-(2-hydroxethyl)-4-phenyl-5H-tetrazol-5-one
• 英文别名: 1-(2-hydroxyethyl)-4-phenyl-1,4-dihydrotetrazol-5-one；4-β-Hydroxyaethyl-1-phenyltetrazolin-5-on；1-(2-Hydroxyethyl)-4-phenyltetrazol-5-one
• CAS: 35727-21-0
• 化学式: C₉H₁₀N₄O₂
• 分子量: 206.204
• InChiKey: YKTAROLSQHWOEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-1-(2-hydroxethyl)-4-phenyl-5H-tetrazol-5-one 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以60%的产率得到1-[2-(acetoxy)ethyl]-4-phenyl-1,4-dihydro-5H-tetrazole-5-one
  参考文献：
  名称：

  Synthesis, antibacterial and QSAR evaluation of 5-oxo and 5-thio derivatives of 1,4-disubstituted tetrazoles

  摘要：

  A series of 1,4-disubstituted tetrazol-5-ones 3a, 5, 7, 12, 13 and 1,4-disubstituted tetrazol-5-thiones 3b, 9, 10 was synthesized and fully characterized by IR, MS, H-1 NMR and C-13 NMR. The series was evaluated for in vitro antibacterial activity against four Gram negative (Escherichia coli, Proteus mirabilis, Klebsiella pneumonia, and Pseudomonas aeruginosa) and three Gram positive (Staphylococcus aureus, Enterococcus faecalis, and Bacillus subtilis) bacteria. The zone of inhibition was measured using the well-diffusion assay, and in vitro minimum inhibitory concentration (MIC) was determined by microbroth dilution assay. MIC values indicate that compounds exhibited a varied range (0.2-37 mu g/mL) of antibacterial activity against the tested bacterial strains. Statistically significant QSAR models were developed by the simple linear regression analysis for the correlation of MIC with computed descriptors. The concluded cross validated regression factors are 0.953 and 0.986 for E. coli, and S. aureus, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.070
• 作为产物：
  描述：

  1-(4-chloro-benzenesulfonyl)-4-phenyl-1,4-dihydro-tetrazol-5-one 、 氢氧化钾 生成 1,4-dihydro-1-(2-hydroxethyl)-4-phenyl-5H-tetrazol-5-one
  参考文献：
  名称：

  DENESKER G.; SMETS G.; LABBE G., TETRAHEDRON , 1975, 31, NO 7, 765-775

  摘要：

  DOI：

文献信息

• Synthesis, spectral characteristics and structure of 1,3- and 1,4-disubstituted tetrazolinones
  作者：Adel Awadallah、Paul Rademacher、Roland Boese

  DOI：10.1002/prac.199533701136

  日期：——

  Reaction of ethylene oxide with 1-alkyl- or 1-aryl-1,4-dihydrotetrazole-5-thiones in acetic acid affords the corresponding mesoionic 1-alkyl- or 1-aryl-3-(2-hydroxyethyl)-tetrazolium-5-olates 4-6. The X-ray structure of one of these compounds (5) is presented. On the other hand, the reaction of tetrazolinones with 2-chloroethanol in the presence of potassium hydroxide affords a mixture of the corresponding 1,3- and 1,4-disubstituted isomers. The isomers can be distinguished easily by their IR, H-1 or C-13 NMR spectra. The fragmentation of these compounds in the mass spectrometer is discussed.