5-(4-methoxyphenyl)-2-trityltetrazole | 439579-44-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-(4-methoxyphenyl)-2-trityltetrazole
• CAS: 439579-44-9
• 化学式: C₂₇H₂₂N₄O
• 分子量: 418.498
• InChiKey: QXSKPCWOTLEIMV-UHFFFAOYSA-N

物化性质

• 沸点：
  611.9±65.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methoxyphenyl)-2-trityltetrazole 以 苯甲腈 为溶剂， 以41%的产率得到3,6-二(4-甲氧苯基)-1,2,4,5-四嗪
  参考文献：
  名称：

  摘要：

  Tritylation of tetrazole and its 5-substituted derivatives with triphenylmethyl chloride under conditions of phase-transfer catalysis regioselectively yields the corresponding 5-substituted 2-trityltetrazoles which can be used to protect N-H bonds in nitrogen-containing heterocycles and O-H bonds in primary alcohols. Thermolysis of 2-trityltetrazoles in benzonitrile leads to 3,6-disubstituted 1,2,4,5-tetrazines. Thermal transformation of the same compounds in dodecane follows a radically different mechanism, resulting in formation of difficultly accessible 8,8-diphenylheptafulvenes. The structure of the latter was proved by X-ray analysis.

  DOI：

  10.1023/a:1021672317335
• 作为产物：
  描述：

  5-(4-甲氧基苯基)-1H-四唑 、 三苯基氯甲烷 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 氯仿 为溶剂， 以55%的产率得到5-(4-methoxyphenyl)-2-trityltetrazole
  参考文献：
  名称：

  摘要：

  Tritylation of tetrazole and its 5-substituted derivatives with triphenylmethyl chloride under conditions of phase-transfer catalysis regioselectively yields the corresponding 5-substituted 2-trityltetrazoles which can be used to protect N-H bonds in nitrogen-containing heterocycles and O-H bonds in primary alcohols. Thermolysis of 2-trityltetrazoles in benzonitrile leads to 3,6-disubstituted 1,2,4,5-tetrazines. Thermal transformation of the same compounds in dodecane follows a radically different mechanism, resulting in formation of difficultly accessible 8,8-diphenylheptafulvenes. The structure of the latter was proved by X-ray analysis.

  DOI：

  10.1023/a:1021672317335

文献信息

• ——
  作者：T. V. Artamonova、L. V. Myznikov、G. I. Koldobskii

  DOI：10.1023/a:1013801413344

  日期：——
• On the relative strength of the 1H-tetrazol-5-yl- and the 2-(triphenylmethyl)-2H-tetrazol-5-yl-group in directed ortho-lithiation
  作者：Patrik Rhonnstad、David Wensbo

  DOI：10.1016/s0040-4039(02)00490-2

  日期：2002.4

  ortho-Lithiation followed by electrophilic trapping of N-unsubstituted and N2-triphenylmethyl substituted 5-aryltetra-zoles, Further Substituted with another ortho-director at the para position of the aryl ring, resulted in the formation of regioisomers of which the ratio depended on the competing para-substituents. By such intramolecular competition experiments, the ortho-directing strength of these tetrazol-5-yl groups in comparison to some commonly employed ortho-directors were found to be: OMe<1H-tetrazol-5-yl