1,4-Dihydro-1-methyl-4-phenyl-5H-tetrazol-5-on | 54246-62-7

• 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-methyl-4-phenyl-5H-tetrazol-5-on
• 英文别名: 1,4-Dihydro-4-methyl-1-phenyl-5H-tetrazol-5-on；1-methyl-4-phenyl-1H-tetrazol-5(4H)-one；4-methyl-1-phenyltetrazol-5-one；1-methyl-4-phenyl-1,4-dihydro-tetrazol-5-one；1-methyl-4-phenyl-1,4-dihydro-tetrazolone；1-Methyl-4-phenyl-1,4-dihydro-tetrazolon；1-methyl-4-phenyltetrazol-5-one
• CAS: 54246-62-7
• 化学式: C₈H₈N₄O
• mdl: MFCD02280645
• 分子量: 176.178
• InChiKey: DDXYULNUXKRXSW-UHFFFAOYSA-N

物化性质

• 熔点：
  71-72 °C
• 沸点：
  234.5±23.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-Dihydro-1-methyl-4-phenyl-5H-tetrazol-5-on 在 tetraphosphorus decasulfide 、 1,4-环己二烯 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 1-甲基-3-苯基硫脲
  参考文献：
  名称：

  Clean Photodecomposition of 1-Methyl-4-phenyl-1H-tetrazole-5(4H)-thiones to Carbodiimides Proceeds via a Biradical

  摘要：

  The photochemistry of 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thione (la) and 1-(3-methoxyphenyl)4-methyl-1H-tetrazole-5(4H)-thione (1b) was studied in acetonitrile at 254 and 300 nm, which involves expulsion of dinitrogen and sulfur to form the respective carbodiimides 5a,b as sole photoproducts. Photolysis of the title compounds in the presence of 1,4-cyclohexadiene trap led to the formation of respective thioureas, providing strong evidence for the intermediacy of a 1,3-biradical formed by the loss of dinitrogen. In contrast, a trapping experiment with cyclohexene provided no evidence to support an alternative pathway of photodecomposition involving initial desulfurization followed by loss of dinitrogen via the intermediacy of a carbene. Triplet sensitization and triplet quenching studies argue against the involvement of a triplet excited state. While the quantum yields for the formation of the carbodiimides 5a,b were modest and showed little change on going from a C6H5 (1a) to mOMeC(6)H(4) (1b) substituent on the tetrazolethione ring, the highly clean photodecomposition of these compounds to a photostable end product makes them promising lead structures for industrial, agricultural, and medicinal applications.

  DOI：

  10.1021/jo1019859
• 作为产物：
  描述：

  1-甲基-4-苯基四唑-5-硫酮 在 水 、 溴 作用下， 生成 1,4-Dihydro-1-methyl-4-phenyl-5H-tetrazol-5-on
  参考文献：
  名称：

  Stolle; Pollecoff; Henke-Stark, Chemische Berichte, 1930, vol. 63, p. 965,969

  摘要：

  DOI：

文献信息

• Fumarate analogs and uses thereof
  申请人：Rigel Pharmaceuticals, Inc.

  公开号：US11129819B2

  公开（公告）日：2021-09-28

  Aspects of the present disclosure include compounds that find use for the treatment of a variety of autoimmune and inflammatory diseases and disorders. Embodiments of the present disclosure also relate to pharmaceutical compositions that include these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

  本公开的各个方面包括可用于治疗各种自身免疫性和炎症性疾病和失调的化合物。本公开的实施方案还涉及包括这些化合物的药物组合物、使用这些化合物治疗各种疾病和失调的方法、制备这些化合物的工艺以及在这些工艺中有用的中间体。
• Electronic properties of 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thiones: An experimental and theoretical study
  作者：Sundeep Rayat、Radhika Chhabra、Olajide Alawode、Aditya S. Gundugola

  DOI：10.1016/j.molstruc.2009.05.049

  日期：2009.9

  The syntheses of 1-(4-methoxyphenyl)1-4-methyl-1H-tetrazol-5(4H)-thione 1a, 1-methyl-4-phenyl-1H-tetrazole-5(4H)-thione 1b, 1-(4-chlorophenyt)-4-methyl-1H-tetrazol-5(4H)-thione 1c, 1-methyl-4-(4-nitrophenyl)-1H-tetrazol-5(4H)-thione 1d were carried out and their electronic absorption spectra were obtained in cyclohexane, THF, and acetonitrile. The UV spectra of la-d showed a modest dependence on the polarity of the solvent. The change of substituent on the tetrazolethione ring from a strongly electron donating group (p-C6H4OMe, 1a), to a moderately electron donating (C6H5, 1b) to a weakly electron withdrawing group (p-C6H4Cl, 1c) also produced minimal effect on the electronic properties of la-c. However, the presence of a strongly electron withdrawing group (p-C6H4NO2, 1d) on the heterocyclic ring produced a marked change in the UV spectrum. Time-dependent density functional calculations revealed that all the bands result from pi ->pi* excitations with some degree of intramolecular charge transfer (ICT) within the molecules. Our studies further showed that as the acceptor strength is increased in the order: la (p-C6H4OMe) < 1b (C6H5) < 1c (p-C6H4Cl) < 1d (p-C6H4NO2), the ICT also increases. In accordance with the experimental observations, the calculated transitions also showed modest dependence on the polarity of the solvent. (C) 2009 Elsevier B.V. All rights reserved.
• Quast, Helmut; Nahr, Uwe, Chemische Berichte, 1985, vol. 118, # 2, p. 526 - 540
  作者：Quast, Helmut、Nahr, Uwe

  DOI：——

  日期：——
• Poplavskaya; Alam; Koldobskii, Russian Journal of Organic Chemistry, 2000, vol. 36, # 12, p. 1793 - 1799
  作者：Poplavskaya、Alam、Koldobskii

  DOI：——

  日期：——
• Quast, Helmut; Fuss, Andreas; Nahr, Uwe, Chemische Berichte, 1985, vol. 118, # 6, p. 2164 - 2185
  作者：Quast, Helmut、Fuss, Andreas、Nahr, Uwe

  DOI：——

  日期：——