5-phenyl-2-(prop-2-yn-1-yl)-2H-tetrazole | 78909-96-3

• 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-phenyl-2-(prop-2-yn-1-yl)-2H-tetrazole
• 英文别名: 2-(2-propynyl)-5-phenyltetrazole；5-phenyl-2-(2-propynyl)tetrazole；2-propargyl-5-phenyltetrazole；5-phenyl-2-prop-2-ynyltetrazole
• CAS: 78909-96-3
• 化学式: C₁₀H₈N₄
• mdl: MFCD14631237
• 分子量: 184.2
• InChiKey: AJNNOCPDVFNUKP-UHFFFAOYSA-N

物化性质

• 熔点：
  45-47 °C
• 沸点：
  344.8±44.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-phenyl-2-(prop-2-yn-1-yl)-2H-tetrazole 在 sodium azide 、 二乙胺盐酸盐 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(5-phenyltetrazol-2-ylmethyl)-1-(tetrazol-5-yl)-1,2,3-trizole
  参考文献：
  名称：

  Synthesis of Polynuclear Nonfused Azoles

  摘要：

  Polynuclear blocks consisting of nonfused heterocycles of the azole series, connected through methylene bridges, were synthesized by successive addition of azole units via cycloaddition of organic azides to the triple bond of N-(2-propynyl)azoles, as well as via reaction of azide ion at the cyano group of cyanomethylazoles. Initial N-(2-propynyl)azoles were prepared by reaction of 2-propynyl bromide with 1,2,3-triazoles, benzotriazole, and tetrazoles; cyanomethylazoles were obtained by alkylation of azoles with chloroacetonitrile. An analogous scheme was used to add heterocyclic units to 2-phenyl-1,2,3-triazole-4-carbonitrile. In this case, the first two heterocyclic units are linked through the ring carbon atom.

  DOI：

  10.1023/b:rujo.0000019746.10504.f3
• 作为产物：
  描述：

  5-苯基四氮唑 、 3-溴丙炔 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以42%的产率得到5-phenyl-2-(prop-2-yn-1-yl)-2H-tetrazole
  参考文献：
  名称：

  含有 1H-1,2,3-三唑基、1H-四唑基和 2H-四唑基片段的新型胸苷类似物的合成和体外生物学评价

  摘要：

  摘要 3'-叠氮胸苷 (AZT) 与 1-propargyl-5-R-1H- 和 2-propargyl-5-R-2H-四唑 (R = H, Me, CH2COOEt, CH2CON(CH3)2, Ph, 2 -CH3-C6H4 或 4-NO2-C6H4) 通过 Cu(I) 催化的不对称 [3 + 2] 环加成得到 3'-修饰的胸苷类似物，其中包含 1H-1,2,3-三唑基、1H-和2H-四唑基片段的产率为 41-76%。所得化合物的结构已通过HRESI+-MS、1H和13C{1H}核磁共振、单晶X射线衍射{对于3'-[4-(1H-5-N,N-二甲氨基羰基甲基四唑- 1-基)-1H-1,2,3-三唑-1-基]胸苷10d}。已对制备的化合物进行体外生物学评价；它们对表型 HIV-1899A 表现出低活性。在 3'-(4-(1H-tetrazol-1-ylmethyl)-1H-1,2,3 的病例中观察到对流感病毒

  DOI：

  10.1080/15257770.2018.1541466

文献信息

• SYNTHESIS OF BIHETEROCYCLIC α-AMINOPHOSPHONIC ACID DERIVATIVES
  作者：S. Achamlale、A. Elachqar、A. El Hallaoui、A. Alami、S. Elhajji、M. L. Roumestant、Ph. Viallefont

  DOI：10.1080/10426509808035736

  日期：1998.9.1

  Abstract We report here the synthesis of biheterocyclic α-aminophosphonic acid derivatives by 1,3 dipolar cycloaddition of acetylenic compounds, prepared in the laboratory, on α-azido α-amino phosphonic esters 1 [1a].

  摘要 我们在此报告了在实验室制备的 α-叠氮基 α-氨基膦酸酯 1 [1a] 上，通过乙炔化合物的 1,3 偶极环加成合成双杂环 α-氨基膦酸衍生物。
• Synthesis and quantitative structure-activity relationship analysis of N-triiodoallyl- and N-iodopropargylazoles. New antifungal agents
  作者：Masao Koyama、Noriko Ohtani、Fumio Kai、Ikuo Moriguchi、Shigeharu Inouye

  DOI：10.1021/jm00386a019

  日期：1987.3

  New series of N-(2,3,3-triiodoallyl) and N-(3-iodopropargyl) azole derivatives (100 compounds) involving pyrrole, pyrazole, imidazole, triazole, and tetrazole nuclei were synthesized successively with the aid of quantitative structure-activity relationship (QSAR) analysis to obtain potent antifungal agents. Starting from the derivatives of nitropyrrole-containing antibiotics, the QSAR analysis of the pyrrole derivatives against Candida albicans and Trichophyton mentagrophytes strains indicated the positive contribution of the nitro group and negative effect of the size of molecule. Further application of the QSAR analysis on the multi-azole derivatives revealed the importance of hydrophobicity and electronegativity as well as steric effect to the activities and led to the synthesis of one of the most potent iodo compounds, 2-(2,3,3-triiodoallyl)tetrazole (67, ME1401).
• Synthesis of polynuclear uncondensed tri- and tetrazoles
  作者：L. I. Vereshchagin、A. V. Maksikova、L. G. Tikhonova、S. R. Buzilova、G. V. Sakovich

  DOI：10.1007/bf00505701

  日期：1981.5
• VERESHCHAGIN L. I.; MAKSIKOVA A. V.; TIXONOVA L. G.; BUZILOVA S. R.; SAKO+, XIMIYA GETEROTSIKL. SOEDIN., 1981, HO 5, 688-693
  作者：VERESHCHAGIN L. I.、 MAKSIKOVA A. V.、 TIXONOVA L. G.、 BUZILOVA S. R.、 SAKO+

  DOI：——

  日期：——