1-(4-乙氧基苯基)-1H-四唑-5-胺 | 238432-78-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(4-乙氧基苯基)-1H-四唑-5-胺
• 英文名称: 1-(4-ethoxyphenyl)-1H-tetrazol-5-amine
• 英文别名: 1-(4-ethoxy-phenyl)-1H-tetrazol-5-ylamine；1-(4-Aethoxy-phenyl)-1H-tetrazol-5-ylamin；5-Amino-1-(P-ethoxyphenyl)tetrazole；1-(4-ethoxyphenyl)tetrazol-5-amine
• CAS: 238432-78-5
• 化学式: C₉H₁₁N₅O
• 分子量: 205.219
• InChiKey: WECXDMDNZSZVKA-UHFFFAOYSA-N

物化性质

• 熔点：
  197 °C
• 沸点：
  406.6±47.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-乙氧基苯基)-1H-四唑-5-胺 在 N,N-二甲基甲酰胺二甲基缩醛 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到{(E)-[1-(ethoxyphenyl)-1H-tetrazol-5-yl]iminomethyl}dimethylamine
  参考文献：
  名称：

  Two derivatives of 1,5-disubstituted tetrazoles: 1-(4-nitrophenyl)-1H-tetrazol-5-amine and {(E)-[1-(4-ethoxyphenyl)-1H-tetrazol-5-yl]iminomethyl}dimethylamine

  摘要：

  The geometric features of 1-(4-nitrophenyl)-1H-tetrazol-5-amine, C7H6N6O2, correspond to the presence of the essential interaction of the 5-amino group lone pair with the pi system of the tetrazole ring. Intermolecular N-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds result in the formation of infinite chains running along the [110] direction and involve centrosymmetric ring structures with motifs R-2(2)(8) and R-2(2)(20). Molecules of {(E)-[1-(4-ethoxyphenyl)-1H-tetrazol-5-yl]iminomethyl}-dimethylamine, C12H16N6O, are essentially flattened, which facilitates the formation of a conjugated system spanning the whole molecule. Conjugation in the azomethine N C -N fragment results in practically the same length for the formal double and single bonds.

  DOI：

  10.1107/s0108270108019707
• 作为产物：
  描述：

  1-(4-乙氧基苯基)-2-硫脲 在 sodium azide 、 碳酸铅(II) 、 乙醇 作用下， 生成 1-(4-乙氧基苯基)-1H-四唑-5-胺
  参考文献：
  名称：

  Stolle et al., Journal fur praktische Chemie (Leipzig 1954), 1932, vol. <2>134, p. 282,297

  摘要：

  DOI：

文献信息

• One-Pot Syntheses of 5-Amino-1-aryltetrazole Derivatives
  作者：Andrey Vorobiov、Pavel Gaponik、Petr Petrov、Oleg Ivashkevich

  DOI：10.1055/s-2006-926403

  日期：2006.4

  A novel facile route for the introduction of 5-amino and 5-alkylamino substituents into 1-aryltetrazoles has been developed. A range of 5-amino-1-aryltetrazoles was obtained directly from the corresponding 1-aryltetrazoles in one pot by consecutive ring-opening, azidation and intramolecular cyclization. 5-Alkylamino-1-aryltetrazoles were formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. An influence of the nature of aryl substituents and reaction conditions on the regioselectivity of the intramolecular cyclization of intermediate guanyl azides is revealed.

  已开发出一种新颖简便的方法，将5-氨基和5-烷基氨基取代基引入到1-芳基四唑中。通过连续的开环、叠氮化和分子内环化反应，从相应的1-芳基四唑一锅获得了一系列5-氨基-1-芳基四唑。5-烷基氨基-1-芳基四唑是通过类似机制从1,4-二取代的四唑盐形成的。研究揭示了芳基取代基的性质和反应条件对中间体氨基叠氮盐分子内环化反应的区域选择性的影响。
• Schelenz, Thomas; Schaefer, Wieland, Advanced Synthesis and Catalysis, 2000, vol. 342, # 2, p. 197 - 200
  作者：Schelenz, Thomas、Schaefer, Wieland

  DOI：——

  日期：——
• Stolle et al., Journal fur praktische Chemie (Leipzig 1954), 1932, vol. <2>134, p. 282,297
  作者：Stolle et al.

  DOI：——

  日期：——
• Two derivatives of 1,5-disubstituted tetrazoles: 1-(4-nitrophenyl)-1<i>H</i>-tetrazol-5-amine and {(<i>E</i>)-[1-(4-ethoxyphenyl)-1<i>H</i>-tetrazol-5-yl]iminomethyl}dimethylamine
  作者：Alexander S. Lyakhov、Andrey N. Vorobiov、Ludmila S. Ivashkevich、Pavel N. Gaponik

  DOI：10.1107/s0108270108019707

  日期：2008.8.15

  The geometric features of 1-(4-nitrophenyl)-1H-tetrazol-5-amine, C7H6N6O2, correspond to the presence of the essential interaction of the 5-amino group lone pair with the pi system of the tetrazole ring. Intermolecular N-H center dot center dot center dot N and N-H center dot center dot center dot O hydrogen bonds result in the formation of infinite chains running along the [110] direction and involve centrosymmetric ring structures with motifs R-2(2)(8) and R-2(2)(20). Molecules of (E)-[1-(4-ethoxyphenyl)-1H-tetrazol-5-yl]iminomethyl}-dimethylamine, C12H16N6O, are essentially flattened, which facilitates the formation of a conjugated system spanning the whole molecule. Conjugation in the azomethine N C -N fragment results in practically the same length for the formal double and single bonds.