3,5-二苯胺基-1,2,4-噻二唑 | 22713-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-二苯胺基-1,2,4-噻二唑
• 英文名称: N³,N⁵-diphenyl-1,2,4-thiadiazole-3,5-diamine
• 英文别名: 3,5-Dianilino-1,2,4-thiadiazol；3-N,5-N-diphenyl-1,2,4-thiadiazole-3,5-diamine
• CAS: 22713-97-9
• 化学式: C₁₄H₁₂N₄S
• 分子量: 268.342
• InChiKey: AFYLMFFIQDHIFP-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  435.3±28.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-二苯胺基-1,2,4-噻二唑 、 碘甲烷 在 sodium hydride 作用下， 生成 dimethylated Dost's base
  参考文献：
  名称：

  Butler, Anthony R.; Glidewell, Christopher; Hussain, Ishtiaq, Journal of Chemical Research, Miniprint, 1980, # 3, p. 1843 - 1863

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基硫脲 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以55%的产率得到3,5-二苯胺基-1,2,4-噻二唑
  参考文献：
  名称：

  Oxidative azacyclization of 1-monosubstituted thioureas in reaction with [bis(acyloxy)iodo]arenes to form 1,2,4-thiadiazole derivatives

  摘要：

  For the first time, derivatives of 1,2,4-thiadiazoles have been obtained by the reaction of [bis(acyloxy)iodo]arenes with 1-monosubstituted thioureas. 1-Acetylthiourea is subject to intermolecular azacyclization to form 3,5-bis-(acetylamino)-1,2,4-thiadiazole in reaction with [bis(acyloxy)iodo] benzene. 1-Phenylthiourea forms 3,5-bis-(phenylamino)-1,2,4-thiadiazole in a single-stage reaction with (diacetoxyiodo)benzene. The reaction of 1-phenylthiourea with [bis(trifluoroacetoxy)iodo]benzene leads to the formation of 5-imino-4-phenyl-3-phenylamino-4H-1,2,4-thiadiazoline. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)01176-1

文献信息

• External oxidant-free electrooxidative intramolecular S-N bond formation for one-pot synthesis for 3,5-disubstituted 1,2,4-thiadiazoles
  作者：Qihao Zhong、Shouri Sheng、Junmin Chen

  DOI：10.1080/10426507.2020.1768093

  日期：2020.12.1

  amidines or guanidines to give the corresponding imidoyl thioureas, which are further cyclized in situ via electrooxidative intramolecular S-N bond formation to promote the final products. This protocol features a metal- and external oxidant-free approach, broad substrate scope, good functional group tolerance, excellent yields, and one-pot operation/reaction without the isolation of the intermediates

  摘要 已在未分离的电解条件下开发了用于合成 5-氨基和 3,5-二氨基取代的 1,2,4-噻二唑衍生物的电化学氧化反应方案。新开发的一锅法涉及异硫氰酸酯与脒或胍反应生成相应的亚氨基硫脲，通过电氧化分子内 SN 键的形成进一步原位环化以促进最终产物。该协议具有无金属和无外部氧化剂的方法、广泛的底物范围、良好的官能团耐受性、优异的产量和一锅操作/反应，无需隔离中间体。图形概要
• Synthesis of 5-Amino and 3,5-Diamino Substituted 1,2,4-Thiadiazoles by I₂-Mediated Oxidative N–S Bond Formation
  作者：Bingnan Wang、Yinggao Meng、Yiming Zhou、Linning Ren、Jie Wu、Wenquan Yu、Junbiao Chang

  DOI：10.1021/acs.joc.7b00814

  日期：2017.6.2

  An oxidative N–S bond formation reaction has been established for 1,2,4-thiadiazole synthesis employing molecular iodine as the sole oxidant. The features of the present reaction include no use of transition metals, mild reaction conditions, simple operation, and short reaction time. This versatile synthetic approach is broadly applicable to a variety of imidoyl and guanyl thiourea substrates to produce

  已经建立了利用分子碘作为唯一氧化剂合成1,2,4-噻二唑的氧化NS键形成反应。本反应的特征包括不使用过渡金属，反应条件温和，操作简单，反应时间短。这种通用的合成方法广泛适用于各种亚氨基和胍基硫脲底物，以有效和可扩展的方式分别生产5-氨基和3,5-二氨基取代的1,2,4-噻二唑衍生物。
• Joshua,C.P., Indian Journal of Chemistry, 1963, vol. 1, p. 391 - 394
  作者：Joshua,C.P.

  DOI：——

  日期：——
• 455. Thiadiazoles. Part III. 3-amino-5-arylamino- and 3 : 5-di(aralkylamino)-1 : 2 : 4-thiadiazoles
  作者：Frederick Kurzer

  DOI：10.1039/jr9560002345

  日期：——
• Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives
  作者：Ana Castro、Arantxa Encinas、Carmen Gil、Stefan Bräse、Williams Porcal、Concepción Pérez、Francisco J. Moreno、Ana Martínez

  DOI：10.1016/j.bmc.2007.09.016

  日期：2008.1

  The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3 beta inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3 beta activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated. (c) 2007 Elsevier Ltd. All rights reserved.

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