1-甲基-4-苯基四唑-5-硫酮 | 1455-91-0

• 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-甲基-4-苯基四唑-5-硫酮
• 英文名称: 1-phenyl-4-methyl-1,4-dihydro-5H-tetrazol-5-thione
• 英文别名: 1,4-Dihydro-1-methyl-4-phenyl-5H-tetrazol-5-thion；1,4-Dihydro-4-methyl-1-phenyl-5H-tetrazol-5-thion；1-methyl-4-phenyl-1H-tetrazole-5(4H)-thione；4-methyl-1-phenyltetrazolethione；1-methyl-4-phenyl-1,4-dihydro-tetrazole-5-thione；1-methyl-4-phenyl-1,4-dihydro-tetrazolethione；5H-Tetrazole-5-thione, 1,4-dihydro-1-methyl-4-phenyl-；1-methyl-4-phenyltetrazole-5-thione
• CAS: 1455-91-0
• 化学式: C₈H₈N₄S
• 分子量: 192.244
• InChiKey: BEVPUUUCHKGPEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基-4-苯基四唑-5-硫酮 在 1,4-环己二烯 作用下， 以 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：

  1,4-Dihydro-1-methyl-4-phenyl-5H-tetrazol-5-on 在 tetraphosphorus decasulfide 作用下， 以 甲苯 为溶剂， 生成 1-甲基-4-苯基四唑-5-硫酮
  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

文献信息

• The photochemistry of 1,4-dihtdro-5h-tetrazole derivatives isolated in low-temperature matrices
  作者：Ian R. Dunkin、Charles J. Shields、Helmut Quast

  DOI：10.1016/0040-4020(89)80053-5

  日期：1989.1

  same diaziridinone obtained previously from solution photolysis, but it also underwent a novel cleavage to MeNCO and, presumably, methyl azide. Iminotetrazolines () and () gave the corresponding carbodiimides () and (), and iminodiaziridines () and (); while the tetrazolinethiones () and () gave carbodiimides () and (), respectively. Photolysis of the vinyl substituted tetrazolinone () proceeded differently

  六种1,4-二氢-5-四唑（四唑啉）衍生物已在12 K的Ar和N 2基质中进行了光解。对MeNCO和大概是叠氮化物的新裂解。亚氨基四唑啉（）和（）得到相应的碳二亚胺（）和（）以及亚氨基二氮丙啶（）和（）；而四唑啉酮（）和（）分别得到碳二亚胺（）和（）。乙烯基取代的四唑啉酮的光解（）在惰性环境温度溶液和低温基质中的处理方式有所不同。在前者中，咪唑酮（）是唯一可分离的产物，而在后者中，二叠氮酮（）的形成与另一种裂解反应竞争，从而得到异氰酸丁酯和叠氮化乙烯基。这些结果最好在中间双基的基础上解释，但是，矩阵ir无法直接检测到。光谱学。
• PROCESS FOR THE PRODUCTION OF TETRAZOLINONES
  申请人：Dynamit Nobel GmbH Explosivstoff- und Systemtechnik

  公开号：EP3560913A1

  公开（公告）日：2019-10-30

  The invention relates to a process for the preparation of a tetrazolinone compound, comprising a step of reacting an isocyanate compound with an azide salt in a solvent and in the presence of a silicon derivative as a catalyst.

  本发明涉及一种制备四唑啉酮化合物的工艺，包括异氰酸酯化合物与叠氮盐在溶剂中并在硅衍生物作为催化剂存在的情况下发生反应的步骤。
• 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.
• SH-Methylation of SH-Containing Heterocycles with Dimethyl Carbonate via Phase-Transfer Catalytic Reaction
  作者：Jian-Gang Xie、Jing Quan、Shu-Bai Li、Yan Zheng、Li-Min Zhu

  DOI：10.1080/00397911003707048

  日期：2011.2.28

  [image omitted] A reaction of SH-containing heterocycles with dimethyl carbonate (DMC) in the presence of K2CO3 and tetrabutylammonium bromide (Bu4NBr) gave heteroaryl methyl thioethers in 44-93% yields. The reaction was carried out under mild conditions. This method provided a useful synthetic method for preparation of various heteroaryl methyl thioethers without the use of toxic methylic halides or dimethyl sulfate.
• Stolle; Pollecoff; Henke-Stark, Chemische Berichte, 1930, vol. 63, p. 965,969
  作者：Stolle、Pollecoff、Henke-Stark

  DOI：——

  日期：——