N,N'-[1,2-bis(4-methylphenyl)-1,2-ethanediylidene]bis-4-methylbenzenamine | 77014-38-1

• 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: N,N'-[1,2-bis(4-methylphenyl)-1,2-ethanediylidene]bis-4-methylbenzenamine
• 英文别名: N,N'-di(p-methylphenyl)-1,2-di(p-methylphenyl)ethane-1,2-diimine；N,N',1,2-tetrakis(4-methylphenyl)ethane-1,2-diimine
• CAS: 77014-38-1
• 化学式: C₃₀H₂₈N₂
• 分子量: 416.566
• InChiKey: YAPINOSSYXKGHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-[1,2-bis(4-methylphenyl)-1,2-ethanediylidene]bis-4-methylbenzenamine 在 盐酸 、 聚合甲醛 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 以29%的产率得到1,3,4,5-tetra(4-methylphenyl)-1H-imidazolium chloride
  参考文献：
  名称：

  Synthesis of Electronically Diverse Tetraarylimidazolylidene Carbenes via Catalytic Aldimine Coupling

  摘要：

  A new method for synthesizing symmetrical N-heterocyclic imidazolium salts is described. Catalytic coupling of aldimines with cyanide followed by oxidation gives alpha-diketimines, which can then be cyclized with formaldehyde in acidic media. This two-step procedure requires no chromatography and allows the synthesis of electronically diverse 1,3,4,5-tetraarylimidazolylidene carbenes.

  DOI：

  10.1021/ol8012765
• 作为产物：
  描述：

  在 对苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N,N'-[1,2-bis(4-methylphenyl)-1,2-ethanediylidene]bis-4-methylbenzenamine
  参考文献：
  名称：

  Synthesis of Electronically Diverse Tetraarylimidazolylidene Carbenes via Catalytic Aldimine Coupling

  摘要：

  A new method for synthesizing symmetrical N-heterocyclic imidazolium salts is described. Catalytic coupling of aldimines with cyanide followed by oxidation gives alpha-diketimines, which can then be cyclized with formaldehyde in acidic media. This two-step procedure requires no chromatography and allows the synthesis of electronically diverse 1,3,4,5-tetraarylimidazolylidene carbenes.

  DOI：

  10.1021/ol8012765

文献信息

• New Synthetic Method for 1,3,4,5-Tetraaryl-2-thioxo-(or -oxo)-2,3-dihydroimidazoles
  作者：K. N. Mehrotra、Geeta Singh

  DOI：10.1055/s-1980-29297

  日期：——
• Singh, Geeta; Mehrotra, Kailash Nath, Heterocycles, 1981, vol. 16, # 8, p. 1341 - 1344
  作者：Singh, Geeta、Mehrotra, Kailash Nath

  DOI：——

  日期：——
• A Novel Reductive Dimerization/Oxidative Dehydrogenation of Aldimines Mediated by Lanthanoid Metals
  作者：Wusong Jin、Yoshikazu Makioka、Tsugio Kitamura、Yuzo Fujiwara

  DOI：10.1021/jo001328d

  日期：2001.1.1

  A lanthanoid metal-mediated novel reductive dimerization/oxidative dehydrogenation of a variety of aldimines has been achieved. Aromatic aldimines (1) were dimerized in the presence of 0.5 mol of ytterbium metal (Yb) and 1-naphthaldehyde (1-NpCHO) to give the corresponding vicinal diimines (2) in good to high yields. Samarium metal (Sm) or samarium(II) diiodide (SmI2) gives unsatisfied yields under the same reaction conditions. As an oxidant, 1-NpCHO gives the best result. In addition, HMPA plays an important role as a cosolvent in this reaction. Reaction of various aldimines with Yb metal is disscussed in detail. Moreover, it has been found that the electron-donating substitutents on the benzene ring promote the reaction and that the electron-withdrawing substitutents retard the reaction. The reaction of deuterated N-benzylideneaniline with Yb metal confirmed that transformation of the hydride occurred from aldimines to the oxidant aldehyde. The mechanism of the reaction was discussed.
• Novel Syntheses of 2-Ethoxy- and 2-Phenoxy-2-oxo-1,3,4,5-tetraaryl-2,3-dihydro-1<i>H</i>-<i>P</i> ^v-1,3,2-diazaphospholes and of 2-Ethoxy-2-thioxo-3,4,5-triaryl-2,3-dihydro-<i>P</i> ^v-1,3,2-oxazaphospholes
  作者：K. N. Mehrotra、I. S. Singh、Jalpana Roy

  DOI：10.1055/s-1985-31117

  日期：——