(1E,2E)-1,2-diphenyl-N¹,N²-di-p-tolylethane-1,2-diimine

• 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: (1E,2E)-1,2-diphenyl-N¹,N²-di-p-tolylethane-1,2-diimine
• 英文别名: 1,4-Bis(4-methylphenyl)-2,3-diphenyl-1,4-diaza-1,3-butadien
• 化学式: C₂₈H₂₄N₂
• 分子量: 388.512
• InChiKey: NDIWSRIOWDPKMM-QAVVBOBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,2-二甲基-1,1,2,2-四氯二硅烷 、 (1E,2E)-1,2-diphenyl-N¹,N²-di-p-tolylethane-1,2-diimine 以 甲苯 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  1.4-Addition of 1.1.2.2-tetrachlorodimethyldisilane to 1.4-diaza-1.3-dienes, synthesis and molecular structure of 1.6-disila-2.5-diaza-1.1.6.6-tetrachloro-1.6-dimethyl-2.5-di-p-tolyl-3.4-diphenyl-hexa-3-ene

  摘要：

  Reaction of 1.1.2.2-tetrachlorodimethyldisilane (4) with 1.4-diazadienes like benzildianil (1), benzildi-p-tolil (2) and benzildi-p-anisil (3) leads to a 1.4-addition product of the disilane under cleavage of the Si-Si bond (1a, 2a, 3a). The structure of 2a was determined by X-ray crystallography (crystal data: monoclinic, P2(1)/n, a = 14.661(4), b = 12.283(2), c = 17.564(5) Angstrom, beta = 103.13 degrees, Z = 4, R = 0.0585 for 5992 independent reflections). Surprisingly, 2a was found to be in the cis-configuration with almost C-2 symmetry and a torsion angle of only 13 degrees. Owing to statistical disorder, some bond lengths are not in the expected range.

  DOI：

  10.1016/s0022-328x(96)06823-4
• 作为产物：
  描述：

  N亚苄基对甲苯胺 在 1-萘甲醛 、 氢化镱 、 碘甲烷 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 4.0h， 以74%的产率得到(1E,2E)-1,2-diphenyl-N¹,N²-di-p-tolylethane-1,2-diimine
  参考文献：
  名称：

  Preparation of vicinal diimines: a new dehydrogenative coupling reaction of aldimines mediated by ytterbium metal

  摘要：

  芳香醛亚胺与镱金属反应，发生脱氢偶联，得到邻位二亚胺化合物，然后用芳香醛如 1-萘醛 (1-NpCHO) 作为氢受体进行处理。

  DOI：

  10.1039/a801514g

文献信息

• Palladium-Catalyzed Diarylation of Isocyanides with Tetraarylleads for the Selective Synthesis of Imines and α-Diimines
  作者：Cong Chi Tran、Shin-ichi Kawaguchi、Yohsuke Kobiki、Hitomi Matsubara、Dat Phuc Tran、Shintaro Kodama、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1021/acs.joc.9b01639

  日期：2019.9.20

  Using tetraaryllead compounds (PbAr4) as arylating reagents, isocyanides undergo selective diarylation in the presence of palladium catalysts such as Pd(OAc)(2) or Pd(PPh3)(4) to afford imines and/or alpha-diimines based on the isocyanide employed. With aliphatic isocyanides, imines are obtained preferentially, whereas alpha-diimines are formed in the case of electron-rich aromatic isocyanides. The differences in imine/alpha-diimine selectivity can be attributed to the stability of imidoylpalladium intermediates formed in this catalytic reaction. Compared with other arylating reagents, tetraaryllead compounds are excellent candidates for use in the selective transformations to imines and/or alpha-diimines, especially in terms of inhibiting the oligomerization of isocyanides, which results in a lower product selectivity in many transition-metal-catalyzed reactions of isocyanides.
• MEHROTRA K. N.; SINGH G., SYNTHESIS, 1980, NO 12, 1001-1004
  作者：MEHROTRA K. N.、 SINGH G.

  DOI：——

  日期：——
• SINGH, GEETA;MEHROTRA, KAILASH, NATH, HETEROCYCLES, 1981, 16, N 8, 1341-1344
  作者：SINGH, GEETA、MEHROTRA, KAILASH, NATH

  DOI：——

  日期：——
• MEHROTRA, K. N.;SINGH, I. S.;ROY, J., SYNTHESIS, BRD, 1985, N 1, 81-83
  作者：MEHROTRA, K. N.、SINGH, I. S.、ROY, J.

  DOI：——

  日期：——
• 1.4-Addition of 1.1.2.2-tetrachlorodimethyldisilane to 1.4-diaza-1.3-dienes, synthesis and molecular structure of 1.6-disila-2.5-diaza-1.1.6.6-tetrachloro-1.6-dimethyl-2.5-di-p-tolyl-3.4-diphenyl-hexa-3-ene
  作者：U. Herzog、G. Roewer、B. Ziemer、B. Herrschaft

  DOI：10.1016/s0022-328x(96)06823-4

  日期：1997.4

  Reaction of 1.1.2.2-tetrachlorodimethyldisilane (4) with 1.4-diazadienes like benzildianil (1), benzildi-p-tolil (2) and benzildi-p-anisil (3) leads to a 1.4-addition product of the disilane under cleavage of the Si-Si bond (1a, 2a, 3a). The structure of 2a was determined by X-ray crystallography (crystal data: monoclinic, P2(1)/n, a = 14.661(4), b = 12.283(2), c = 17.564(5) Angstrom, beta = 103.13 degrees, Z = 4, R = 0.0585 for 5992 independent reflections). Surprisingly, 2a was found to be in the cis-configuration with almost C-2 symmetry and a torsion angle of only 13 degrees. Owing to statistical disorder, some bond lengths are not in the expected range.