(Z)-1,2-diphenyl-N,N'-di(p-methylphenyl)ethylene-1,2-diamine | 24099-52-3

• 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: (Z)-1,2-diphenyl-N,N'-di(p-methylphenyl)ethylene-1,2-diamine
• 英文别名: α,α'-di-p-toluidino-stilbene；α,α'-Di-p-toluidino-stilben；ms-p-Toluidino-desoxybenzoin-p-tolylimid；α,α'-Di-p-toluidinstilben；(Z)-N,N'-bis(4-methylphenyl)-1,2-diphenylethene-1,2-diamine
• CAS: 24099-52-3
• 化学式: C₂₈H₂₆N₂
• 分子量: 390.528
• InChiKey: JYUDFAWEYQDODN-DQSJHHFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1,2-diphenyl-N,N'-di(p-methylphenyl)ethylene-1,2-diamine 在 盐酸 、 乙醇 作用下， 生成 2-[(4-甲基苯基)氨基]-1,2-二苯基-乙酮
  参考文献：
  名称：

  Strain, Journal of the American Chemical Society, 1929, vol. 51, p. 272

  摘要：

  DOI：
• 作为产物：
  描述：

  氰化钾 、 N亚苄基对甲苯胺 在 氨 作用下， 生成 (Z)-1,2-diphenyl-N,N'-di(p-methylphenyl)ethylene-1,2-diamine
  参考文献：
  名称：

  Strain, Journal of the American Chemical Society, 1928, vol. 50, p. 2221

  摘要：

  DOI：

文献信息

• Ene-diamine versus Imine-amine Isomeric Preferences
  作者：B. Jesse E. Reich、Erin E. Greenwald、Aaron K. Justice、Brittany T. Beckstead、Joseph H. Reibenspies、Simon W. North、Stephen A. Miller

  DOI：10.1021/jo051102g

  日期：2005.10.1

  Cyanide-catalyzed aldimine coupling was employed to synthesize compounds with 1,2-ene-diamine and alpha-imine-amine structural motifs: 1,2,N,N'-tetraphenyletheylene-1,2-diamine (13) and (+/-)-2,3-di-(2-hydroxyphenyl)-1,2-dihydroquinoxaline (17), respectively. Single-crystal X-ray diffraction provided solid-state structures and density functional theory calculations were used to probe isomeric preferences within this and the related hydroxy-ketone/ene-diol system. The ene-diamine and imineamine core structures were calculated (B3LYP/6-311++G(d,p)) to be essentially identical in energy (Delta G = 0.2 kcal/mol in favor of the imine-amine, within the error of the calculation). However, additional effects-such as pi conjugation-in 13 render an ene-diamine structure that is slightly more stable than the imine-amine tautomer (14) (Delta G = 0.2-0.7 kcal/mol, within the error of the calculation). In contrast, the intramolecular hydrogen bonding present in 17 significantly favors the imine-amine isomer over the ene-diamine tautomer (18) (Delta G = 7.2-8.9 kcal/mol). For both 13 and 17, the optimized calculated structures (B3LYP/6-31+G(d')) are identical to those observed by single-crystal X-ray diffraction.