1-(3-methoxyphenyl)-1,4-dihydro-5H-tetrazol-5-one | 133088-17-2

• 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-(3-methoxyphenyl)-1,4-dihydro-5H-tetrazol-5-one
• 英文别名: 1-(3-methoxyphenyl)-1H-tetrazol-5(4H)-one；4-(3-methoxyphenyl)-1H-tetrazol-5-one
• CAS: 133088-17-2
• 化学式: C₈H₈N₄O₂
• 分子量: 192.177
• InChiKey: ROFCYRAZVRVRCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3-methoxyphenyl)-1,4-dihydro-5H-tetrazol-5-one 在 tetraphosphorus decasulfide 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 1-(3-methoxyphenyl)-4-methyl-1H-tetrazole-5(4H)-thione
  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：

  3-甲氧基苯异氰酸 在 叠氮基三甲基硅烷 作用下， 生成 1-(3-methoxyphenyl)-1,4-dihydro-5H-tetrazol-5-one
  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

• [EN] TETRAZOLONE SUBSTITUTED STEROIDS AND USE THEREOF<br/>[FR] STÉROÏDES À SUBSTITUTION TÉTRAZOLONE ET UTILISATION DE CES DERNIERS
  申请人：BEIJING XUANYI PHARMASCIENCES CO LTD

  公开号：WO2020150210A1

  公开（公告）日：2020-07-23

  The present disclosure relates to compounds of formula (AI), (I), (AII), and (II), or a pharmaceutically acceptable salt, solvate, stereoisomer, or tautomer thereof, a pharmaceutical composition comprising a compound of formula (AI), (I), (AII), and (II), and use thereof, wherein R2, R3, R4, R5, R6, R7, R10, R11a, R11b, R12, R16, R19a, R19b, and R20 are described herein. Such compounds are envisioned useful for the prevention and treatment of a variety of CNS-related conditions, for example, treatment of sleep disorders, mood disorders, movement disorders, convulsive disorders, schizophrenin spectrum disorders, disorders of memory and/or cognition, personality disorders, autism spectrum disorders, pain, traumatic brain injury, vascular diseases, substance abuse disorders and/or withdrawal syndromes, or tinnitus etc.

  本公开涉及式（AI）、（I）、（AII）和（II）的化合物，或者其药学上可接受的盐、溶剂合物、立体异构体或互变异构体，包括含有式（AI）、（I）、（AII）和（II）的化合物的药物组合物及其使用，其中R2、R3、R4、R5、R6、R7、R10、R11a、R11b、R12、R16、R19a、R19b和R20如本文所述。这些化合物被设想用于预防和治疗各种与中枢神经系统有关的疾病，例如睡眠障碍、情绪障碍、运动障碍、癫痫性障碍、精神分裂谱系障碍、记忆和/或认知障碍、人格障碍、自闭症谱系障碍、疼痛、创伤性脑损伤、血管疾病、物质滥用障碍和/或戒断综合征，或耳鸣等。
• COVEY, RUPERT A.;FORBES, PATRICIA J.;BELL, ALLYN R.;BLEM, ALLEN R.
  作者：COVEY, RUPERT A.、FORBES, PATRICIA J.、BELL, ALLYN R.、BLEM, ALLEN R.

  DOI：——

  日期：——
• TETRAZOLINONE COMPOUNDS AND ITS USE AS PESTICIDES
  申请人：Sumitomo Chemical Company Limited

  公开号：EP2841429B1

  公开（公告）日：2020-10-21
• TETRAZOLONE SUBSTITUTED STEROIDS AND USE THEREOF
  申请人：Beijing Xuanyi Pharmasciences Co., Ltd.

  公开号：EP3911331A1

  公开（公告）日：2021-11-24
• US9565856B2
  申请人：——

  公开号：US9565856B2

  公开（公告）日：2017-02-14