2,4-二苯基-3-氨基硫脲 | 13207-47-1

• 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: 2,4-二苯基-3-氨基硫脲
• 英文名称: 2,4-diphenyl-thiosemicarbazide
• 英文别名: 2,4-Diphenyl-thiosemicarbazid；1-Amino-1,3-diphenylthiourea
• CAS: 13207-47-1
• 化学式: C₁₃H₁₃N₃S
• 分子量: 243.332
• InChiKey: AIONMUKAPQSLHW-UHFFFAOYSA-N

物化性质

• 沸点：
  383.5±25.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.4
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  2,4-二苯基-3-氨基硫脲 在 甲苯 、 苯 作用下， 生成 1,4-diphenyl-5-thio-1,2,4-triazolidin-3-one
  参考文献：
  名称：

  Busch, Chemische Berichte, 1909, vol. 42, p. 4766

  摘要：

  DOI：
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 苯肼 在 乙醇 作用下， 生成 2,4-二苯基-3-氨基硫脲
  参考文献：
  名称：

  Marckwald, Chemische Berichte, 1892, vol. 25, p. 3106,3107

  摘要：

  DOI：

文献信息

• A quantitative study of substituent effects on oxidative cyclization of some 2-aryl-substituted aldehyde thiosemicarbazones induced by ferric chloride and cupric perchlorate
  作者：Renato Noto、Paolo Lo Meo、Michelangelo Gruttadauria、Giuseppe Werber

  DOI：10.1002/jhet.5570360315

  日期：1999.5

  As a development of our previous work, we performed a kinetic study of the oxidative cyclization reaction of some 2,4-diaryl-substituted aldehyde thiosemicarbazones 1a-n induced by ferric chloride and by cupric perchlorate. The results of cyclization of 1a-n were compared to those of the corresponding 2-methyl derivatives. The kinetic data were analyzed by means of the Hammett's equation.

  作为我们先前工作的发展，我们对氯化铁和高氯酸铜诱导的一些2,4-二芳基取代的醛硫代半碳唑酮1a-n的氧化环化反应进行了动力学研究。将1a-n的环化结果与相应的2-甲基衍生物的环化结果进行了比较。通过哈米特方程分析动力学数据。
• The Chemistry of Stable Carbenes. Part 2. Benzoin-type condensations of formaldehyde catalyzed by stable carbenes
  作者：J. Henrique Teles、Johann-Peter Melder、Klaus Ebel、Regina Schneider、Eugen Gehrer、Wolfgang Harder、Stefan Brode、Dieter Enders、Klaus Breuer、Gerhard Raabe

  DOI：10.1002/hlca.19960790108

  日期：1996.2.7

  Stable carbenes derived from thiazole, 1H-imidazole, and 4H-1,2,4-triazole are efficient catalysts for benzointype condensations of formaldehyde. Catalysts derived from N-substituted thiazolium salts trimerize formaldehyde to dihydroxyacetone (II). Catalysts based on 1,4-disubstituted 4H-1,2,4-triazol-1-ium salts give glycolaldehyde (I) as the main product and no II, whereas N,N′-disubstituted 1H-imidazol-3-ium

  衍生自噻唑，1 H-咪唑和4 H -1,2,4-三唑的稳定卡宾是甲醛的苯偶姻型缩合反应的有效催化剂。由N-取代的噻唑鎓盐衍生的催化剂将甲醛三聚为二羟基丙酮（II）。基于1,4-二取代的4 H -1,2,4-三唑-1-鎓盐的催化剂以乙醇醛（I）为主要产物而没有II，而N，N'-二取代的1 H-咪唑-3-铵盐产生两种产物的混合物。在催化循环中分离几种中间体可以更好地了解反应机理。
• The Reactivity of Dimethyl Acetylenedicarboxylate and Heterocyclization of Hydrazinecarbothioamides to 1,3-Thiazolidin-4-ones
  作者：Alaa A. Hassan、Nasr K. Mohamed、Kamal M. A. El-Shaieb、Hendawy N. Tawfeek、Stefan Bräse、Martin Nieger

  DOI：10.1002/jhet.2392

  日期：2016.1

  2‐Substituted hydrazinecarbothioamides and N,2‐disubstituted hydrazinecarbothioamides react, in high yields with dimethyl acetylenedicarboxylate to give 4‐oxo‐Z‐(thiazolidin‐5‐ylidene)acetate derivatives. Several mechanistic options involving interaction are presented. The structures of thiazolidin‐4‐ones have been unambiguously confirmed by single crystal X‐ray crystallography.

  2-取代的肼基甲硫基酰胺和N，2-二取代的肼基甲硫基酰胺与乙炔二羧酸二甲酯高产率反应，得到4-氧代Z-（噻唑烷酮-5-亚烷基）乙酸酯衍生物。介绍了涉及相互作用的几种机械选择。噻唑烷丁-4-酮的结构已通过单晶X射线晶体学明确证实。
• Formation of Indazole Derivatives from 2,4-Disubstituted Thiosemicarbazides and some Chloro-<i>p</i>-Quinones
  作者：Alaa A. Hassan、Ashraf A. Aly、Mamdouh A. Mohamed

  DOI：10.3184/030823410x12797029344957

  日期：2010.8

  The reaction of 2,4-disubstituted thiosemicarbazides with 2,3,5,6-tetrachloro-1,4-benzo-quinone gave 2-aryl-5,6-dichloro-3-(substituted imino)-2,3-dihydro-1 H-indazole-4,7-diones in 57–66% yield together with smaller amounts of 2-aryl-3-(substituted imino)-4,6,7-trichloro-2 H-indazole-5(3 H)-ones (21–25% yield). Reaction of 2,3-dichloro-1,4-naphthoquinone with 2,4-disubstituted thiosemicarbazides provided 2-aryl-3-(substituted imino)-2,3-dihydro-1 H-benzo[ f]-indazole-4,9-diones in 63–74% yield. Rationales for these transformations are presented.

  2,4-二取代的硫代氨基甲酸与 2,3,5,6-四氯-1,4-苯醌反应，得到 2-芳基-5,6-二氯-3-（取代的亚氨基）-2,3-二氢-1 H-吲唑-4,7-二酮（收率为 57-66%）以及少量 2-芳基-3-（取代的亚氨基）-4,6,7-三氯-2 H-吲唑-5(3H)-酮（收率为 21-25%）。2,3-二氯-1,4-萘醌与 2,4-二取代的硫代氨基甲酸反应生成了 2-芳基-3-（取代的亚氨基）-2,3-二氢-1 H-苯并[f]-吲唑-4,9-二酮，收率为 63-74%。本文介绍了这些转化的原理。
• Conventional and microwave irradiation assisted synthesis of new 1,2,4‐triazepine‐3‐thiones
  作者：Ashraf A. Aly、Alaa A Hassan、Essmat M. El‐Sheref、Mamdouh A. Mohamed、Alan B. Brown

  DOI：10.1002/jhet.5570450234

  日期：2008.3

  New 1,2,4-triazepine-3-thiones have been obtained during the respective reactions of N-substituted-hydrazino carbothioamides with dimethyl acetylenedicarboxylate and dibenzoyl acetylene under prolonged reflux in acetic acid and/or DMF. However, the reaction of the starting materials in DMF under microwave irradiation afforded the same products in higher yields within a few minutes.

  在乙酸和/或DMF中长时间回流下，N-取代的肼基碳硫代酰胺与乙炔基二羧酸二甲酯和二苯甲酰基乙炔的各自反应过程中，获得了新的1,2,4-三氮杂-3-硫酮。但是，在微波辐射下，起始原料在DMF中的反应在几分钟内以较高的收率提供了相同的产物。