4,4'-bis-ethylsulfanyl-2,2'-diphenyl-N5,N5'-di-(4-tolyl)-4H,4'H-[4,4']biimidazolyl-5,5'-diamine | 328378-56-9

• 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: 4,4'-bis-ethylsulfanyl-2,2'-diphenyl-N5,N5'-di-(4-tolyl)-4H,4'H-[4,4']biimidazolyl-5,5'-diamine
• 英文别名: 5-ethylsulfanyl-5-[4-ethylsulfanyl-5-(4-methylanilino)-2-phenylimidazol-4-yl]-N-(4-methylphenyl)-2-phenylimidazol-4-amine
• CAS: 328378-56-9
• 化学式: C₃₆H₃₆N₆S₂
• 分子量: 616.854
• InChiKey: AXQXWLJKOZTLDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-bis-ethylsulfanyl-2,2'-diphenyl-N5,N5'-di-(4-tolyl)-4H,4'H-[4,4']biimidazolyl-5,5'-diamine 在 tetraphenylporphyrine 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以58%的产率得到2-phenyl-5-(4-tolylamino)-imidazol-4-one
  参考文献：
  名称：

  Nucleophilic Substitution of 4H-Imidazolesby Thioles: New Starting Materials for Tetraazafulvalenes and Fused Heterocycles

  摘要：

  Different reactivities towards the 4H-imidazoles 1 depending on the nature of the sulfur containing nucleophile were observed. Whereas H2S and aromatic thioles led to 4,5-diamino-imidazoles in the course of a reduction process, treatment with aliphatic mercaptanes resulted in a substitution-reduction-dimerization cascade which finally gave bis-imidazoles. Their oxidative modification in presence of m-chloroperbenzoic acid then allowed new 1,3,5,7-tetraazafulvalenes to be easily obtained. Treatment of the bis-imidazoles with acetylene dimethyldicarboxylate caused cleavage of the central bond, thus leading to the formation of derivatives which are of interest for the transformation into fused heterocycles such as imidazo[4,5-b]azepines.

  DOI：

  10.1007/s007060070026
• 作为产物：
  描述：

  乙硫醇 、 [5-(4-Methylphenylamino)-4-(4-methylphenylimino)-4H-imidazol-2-yl]-benzene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到4,4'-bis-ethylsulfanyl-2,2'-diphenyl-N5,N5'-di-(4-tolyl)-4H,4'H-[4,4']biimidazolyl-5,5'-diamine
  参考文献：
  名称：

  Nucleophilic Substitution of 4H-Imidazolesby Thioles: New Starting Materials for Tetraazafulvalenes and Fused Heterocycles

  摘要：

  Different reactivities towards the 4H-imidazoles 1 depending on the nature of the sulfur containing nucleophile were observed. Whereas H2S and aromatic thioles led to 4,5-diamino-imidazoles in the course of a reduction process, treatment with aliphatic mercaptanes resulted in a substitution-reduction-dimerization cascade which finally gave bis-imidazoles. Their oxidative modification in presence of m-chloroperbenzoic acid then allowed new 1,3,5,7-tetraazafulvalenes to be easily obtained. Treatment of the bis-imidazoles with acetylene dimethyldicarboxylate caused cleavage of the central bond, thus leading to the formation of derivatives which are of interest for the transformation into fused heterocycles such as imidazo[4,5-b]azepines.

  DOI：

  10.1007/s007060070026

文献信息

• Nucleophilic Substitution of 4H-Imidazolesby Thioles: New Starting Materials for Tetraazafulvalenes and Fused Heterocycles
  作者：Jens Atzrodt、Rainer Beckert、Helmar Görls

  DOI：10.1007/s007060070026

  日期：2000.11.13

  Different reactivities towards the 4H-imidazoles 1 depending on the nature of the sulfur containing nucleophile were observed. Whereas H2S and aromatic thioles led to 4,5-diamino-imidazoles in the course of a reduction process, treatment with aliphatic mercaptanes resulted in a substitution-reduction-dimerization cascade which finally gave bis-imidazoles. Their oxidative modification in presence of m-chloroperbenzoic acid then allowed new 1,3,5,7-tetraazafulvalenes to be easily obtained. Treatment of the bis-imidazoles with acetylene dimethyldicarboxylate caused cleavage of the central bond, thus leading to the formation of derivatives which are of interest for the transformation into fused heterocycles such as imidazo[4,5-b]azepines.