4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione | 1195504-76-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
• 英文别名: 4,5-dihydroxy-1,3-dimethyl-4,5-diphenylimidazolidine-2-thione
• CAS: 1195504-76-7
• 化学式: C₁₇H₁₈N₂O₂S
• 分子量: 314.408
• InChiKey: ZNCACVCTXQXADM-UHFFFAOYSA-N

物化性质

• 熔点：
  158-159 °C
• 沸点：
  539.6±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Biltz, Chemische Berichte, 1909, vol. 42, p. 1799

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N'-二甲基硫脲 、 联苯甲酰 在 sodium hydroxide 作用下， 反应 0.03h， 以95%的产率得到4,5-dihydroxy-1,3-dimethyl-4,5-diphenyltetrahydroimidazole-2-thione
  参考文献：
  名称：

  4,5-二羟基-1,3-二烷基-4,5-二芳基咪唑烷-2-硫酮和硫乙内酰脲的微波辅助固相合成

  摘要：

  摘要 4,5-二羟基-1,3-二烷基-4,5-二芳基咪唑烷-2-硫酮由苄基衍生物与硫脲衍生物在固相中以1:1的加成反应得到，收率良好。这些化合物经历平稳的重排，然后发生氢转移，以极好的收率生产乙内酰脲。

  DOI：

  10.1080/00397911.2010.503000

文献信息

• 4,5-Dihydroxyimidazolidin-2-ones in an α-ureidoalkylation reaction of N-(carboxyalkyl)-, N-(hydroxyalkyl)-, and N-(aminoalkyl)ureas 3. α-Ureidoalkylation of N-[2-(dimethylamino)ethyl]urea
  作者：G. A. Gazieva、P. V. Lozhkin、V. V. Baranov、Yu. V. Nelyubina、A. N. Kravchenko、N. N. Makhova

  DOI：10.1007/s11172-009-0348-0

  日期：2009.12

  α-Ureidoalkylation of N-[2-(dimethylamino)ethyl]urea with 1,3-unsubstituted, 1,3-dialkyl-, and 1,3-dimethyl-4,5-diphenyl-4,5-dihydroxyimidazolidin-2-ones(thiones) was systematically studied. Hitherto unknown N-[2-(dimethylamino)ethyl]glycolurils and their hydrochlorides were synthesized. The yields of the target glycoluril hydrochlorides decreased on going from 1,3-H2- to 1,3-dialkyl-4,5-dihydroxyimidazolidin-2-ones and increased with the introduction of phenyl groups at the positions 4 and 5 of the starting 4,5-dihydroxyimidazolidin-2-one. X-ray diffraction study showed that 2-[2-(dimethylamino)ethyl]glycoluril crystallizes in the form of a conglomerate.

  系统研究了 N-[2-(二甲基氨基)乙基]脲与 1,3-未取代的、1,3-二烷基和 1,3-二甲基-4,5-二苯基-4,5-二羟基咪唑烷-2-酮（亚硫酸盐）的α-脲烷基化反应。合成了迄今未知的 N-[2-（二甲基氨基）乙基]甘氨酰脲及其盐酸盐。从 1,3-H2- 到 1,3- 二烷基-4,5-二羟基咪唑烷-2-酮，目标甘糖醇盐酸盐的产率有所下降，而在起始的 4,5-二羟基咪唑烷-2-酮的第 4 和第 5 位引入苯基后，产率则有所上升。X 射线衍射研究表明，2-[2-(二甲基氨基)乙基]甘氨酰脲以聚合体形式结晶。
• Diastereoselective synthesis of 4,5-dihydroxyimidazolidin-2-ones (-thiones) and their structure
  作者：A. N. Kravchenko、V. V. Baranov、Yu. V. Nelyubina、G. A. Gazieva、I. V. Svitan’ko

  DOI：10.1007/s11172-012-0010-0

  日期：2012.1

  Studies on the synthesis of 4,5-dihydroxyimidazolidin-2-ones (-thiones) based on the condensation of ureas or thioureas with glyoxal or 1,2-dioxo-1,2-diphenylethane showed high diastereoselectivity in the formation of racemates (trans-diastereomers) of 4,5-dihydroxyimidazolidin-2-ones (-thiones) and meso-forms (cis-diastereomers) of 4,5-dihydroxy-4,5-diphenyl-1,3-dialkylimidazolidine-2-thiones; plausible mechanisms of their formation were suggested. X-ray diffraction studies confirmed structures of diastereomers for separate examples of racemates and meso-forms of 4,5-dihydroxyimidazolidin-2-ones (-thiones).

  基于脲类或硫脲类与乙二醛或 1,2-二氧代-1.2-二苯基乙烷缩合合成 4,5-二羟基咪唑烷-2-酮（-thiones）的研究表明，4,5-二羟基咪唑烷-2-酮（-thiones）的外消旋体（反式-非对映异构体）的形成具有高度非对映选择性、2-二苯基乙烷缩合而成的 4,5-二羟基咪唑烷-2-酮（-硫酮）的外消旋体（反式-非对映异构体）和 4,5-二羟基-4,5-二苯基-1,3-二烷基咪唑烷-2-硫酮的中间体（顺式-非对映异构体）的非对映选择性很高；提出了它们的合理形成机制。X 射线衍射研究证实了 4,5-二羟基咪唑烷-2-酮（-硫酮）外消旋体和中消旋体的非对映异构体结构。
• α-Thioureidoalkylation of functionally substituted ureas: II. Synthesis of thio analogs of N-hydroxyalkyl-1,5-diphenylglycolurils
  作者：G. A. Gazieva、V. V. Baranov、A. N. Kravchenko、N. N. Makhova

  DOI：10.1134/s1070428011100216

  日期：2011.10

  Reactions of N-(hydroxyalkyl)ureas with 4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones gave previously unknown 4,6-dialkyl-1-hydroxyalkyl-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-2-ones which may be regarded as thio analogs of N-(hydroxyalkyl)glycolurils.
• α-Thioureidoalkylation of functionally substituted ureas: I. Tandem cyclization and esterification in reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in alcohols
  作者：V. V. Baranov、G. A. Gazieva、Yu. V. Nelyubina、A. N. Kravchenko、N. N. Makhova

  DOI：10.1134/s1070428011100204

  日期：2011.10

  Acid-catalyzed reactions of N-(carboxyalkyl)ureas with 1,3-dialkyl-4,5-dihydroxy-4,5-diphenylimidazolidine-2-thiones in methanol or propan-2-ol led to the formation of previously unknown omega-(4,6-dialkyl-2-oxo-3a,6a-diphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)alkanoic acids and their methyl and isopropyl esters. The structure of some esters was proved by X-ray analysis. Methyl (4,6-diethyl-2-oxo-3a,6adiphenyl-5-thioxooctahydroimidazo[4,5-d]imidazol-1-yl)acetate showed anxiolytic effect.
• Broan, Christopher J.; Butler, Anthony R.; Reed, David, Journal of the Chemical Society. Perkin transactions II, 1989, p. 731 - 740
  作者：Broan, Christopher J.、Butler, Anthony R.、Reed, David、Sadler, Ian H.

  DOI：——

  日期：——