5,5-Diphenyl-2-methylmercapto-4-oxo-imidazoline | 22544-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5-Diphenyl-2-methylmercapto-4-oxo-imidazoline
• 英文别名: 2-methylsulfanyl-5,5-diphenyl-1,5-dihydro-imidazol-4-one；2-Methylmercapto-5,5-diphenyl-1,5-dihydro-imidazol-4-on；2-Methylmercapto-5,5-diphenyl-2-imidazolinon-(4)；2-Methylmercapto-5.5-diphenyl-2-imidazolin-4-on；2-methylsulfanyl-4,4-diphenyl-1H-imidazol-5-one
• CAS: 22544-70-3
• 化学式: C₁₆H₁₄N₂OS
• 分子量: 282.366
• InChiKey: BZKRCQPNGBABHM-UHFFFAOYSA-N

物化性质

• 熔点：
  213 °C
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-Diphenyl-2-methylmercapto-4-oxo-imidazoline 在 盐酸 作用下， 生成 3-甲基-5,5-二苯基海因
  参考文献：
  名称：

  Cattelain; Chabrier, Bulletin de la Societe Chimique de France, 1947, p. 639,641

  摘要：

  DOI：
• 作为产物：
  描述：

  5,5-二苯基-2-硫代海因 以85%的产率得到
  参考文献：
  名称：

  CHIANG, HUNG-CHEN;KO, JIN-REN, HETEROCYCLES, 1982, 19, N 3, 529-530

  摘要：

  DOI：

文献信息

• Synthesis, Structure and Properties of 5,5-Diphenyl-2,3,5,6-tetrahydroimidazo-[2,1-b]-imidazoline-3,6-dione
  作者：Katarzyna Kieć-Kononowicz、Janina Karolak-Wojciechowska、Agnieszka Mrozek、Maciej Posel

  DOI：10.1002/ardp.19953280608

  日期：——

  Cyclization of N‐[(5,5‐diphenyl)‐4‐oxo‐2‐imidazolidinyl]glycine (3) yielded 5,5‐diphenyl‐2,3,5,6‐tetrahydroimidazo[2,1‐b]imidazoline‐3,6‐dione (6) or its acetyl derivative 5 depending on the method used. The stabilities of 5 and 6 in acidic or alkaline solutions were examined. The crystal structure of the hydrolysis products 7,8 of 5 and 6 were solved by X‐ray analysis.

  N - [(5,5 - 二苯基) -4 - 氧代 - 2 - 咪唑啉基] 甘氨酸 (3) 环化生成 5,5 - 二苯基 - 2,3,5,6 - 四氢咪唑 [2,1 - b] 咪唑啉 - 3,6-二酮 (6) 或其乙酰衍生物 5 取决于所使用的方法。检查了 5 和 6 在酸性或碱性溶液中的稳定性。5 和 6 的水解产物 7,8 的晶体结构通过 X 射线分析解析。
• 79. Thiohydantoins. Part III. The N- and S-methyl derivatives of 5 : 5-disubstituted hydantoins and their mono- and di-thioanalogues
  作者：H. C. Carrington、W. S. Waring

  DOI：10.1039/jr9500000354

  日期：——
• Biltz, Chemische Berichte, 1909, vol. 42, p. 1799
  作者：Biltz

  DOI：——

  日期：——
• Fragmentations of 5,5-diphenylmonothiohydantoins and theirN- andS-methyl derivatives after electron impact
  作者：U. I. Záhorszky、J. Nyitrai、K. Zauer

  DOI：10.1002/oms.1210190107

  日期：1984.1

  AbstractThe mass spectra of 5,5‐diphenylmonothiohydantoins and their N‐ and S‐methyl derivatives have been investigated and interpreted in terms of structural correlations. All stable isomers can be easily distinguished by their fragmentation patterns.
• Synthesis and anticonvulsant activity of 2-iminohydantoins
  作者：Chul Hoon Kwon、Muhammad Tahir Iqbal、John N. D. Wurpel

  DOI：10.1021/jm00110a013

  日期：1991.6

  Iminohydantoins selectively substituted at position C-5 and their 1-carbobenzoxy derivatives have been synthesized, and their anticonvulsant activity was evaluated in mice. In general the more lipophilic 1-carbobenzoxy iminohydantoins were more potent than the unsubstituted counterparts. Evaluation of the individual enantiomers of the chiral iminohydantoins showed that the anticonvulsant activity resided primarily in the S isomers. In this study, (S)-(+)-1-carbobenzoxy-5-isobutyl-2-iminohydantoin (9a) was the most active member. This compound was not nearly as active as phenytoin against electrically induced convulsions, but was also active against pentylenetetrazole-induced seizures, suggesting a broader clinical potential. The closest analogue of phenytoin, viz., 5,5-diphenyl-2-iminohydantoin (1), failed to show any significant activity. Methylation on N-3 or the imino nitrogen of 1 also did not provide a compound with substantial activity. 2-Thiophenytoin was not active against electroshock seizures and showed only a weak activity against pentylenetetrazole. This study suggested that the structure-activity relationship of 2-iminohydantoins was quite different from that of 2-hydantoins.