N,N'-diphenyl-1,2-di(p-methoxyphenyl)ethane-1,2-diimine | 21854-89-7

• 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'-diphenyl-1,2-di(p-methoxyphenyl)ethane-1,2-diimine
• 英文别名: 4,4'-dimethoxybenzilbis(phenylimine)；α,α'-Bis-(phenylimino)-p,p'-bis-(methoxy)-dibenzyl；4,4'-Dimethoxybenzil-dianil；4.4'-Dimethoxybenzildianil；1,2-bis(4-methoxyphenyl)-N,N'-diphenylethane-1,2-diimine
• CAS: 21854-89-7
• 化学式: C₂₈H₂₄N₂O₂
• 分子量: 420.511
• InChiKey: CAZWIUFQHGHKHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-diphenyl-1,2-di(p-methoxyphenyl)ethane-1,2-diimine 在 盐酸 、 聚合甲醛 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 以32%的产率得到4,5-bis(4-methoxyphenyl)-1,3-diphenyl-1H-imidazol-3-ium 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：

  (4-methoxy-phenyl)-phenylimino-acetonitrile 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以72%的产率得到N,N'-diphenyl-1,2-di(p-methoxyphenyl)ethane-1,2-diimine
  参考文献：
  名称：

  A Novel Decyanogenative Coupling of α-Cyanoimines Mediated by Samarium. A Facile Route to α-Diketimines

  摘要：

  α-氰亚胺1转化为α-二酮亚胺2已成功实现，采用干燥的四氢呋喃中的二碘锶，反应产率高，并且没有生成联苯胺3、1,2-二胺4或酰胺5。

  DOI：

  10.1246/cl.2004.102

文献信息

• Electronically tunable N-heterocyclic carbene ligands: 1,3-diaryl vs. 4,5-diaryl substitution
  作者：James W. Ogle、Stephen A. Miller

  DOI：10.1039/b914732b

  日期：——

  The catalytic activity of iridium-mediated transfer hydrogenation is readily tuned by electronic variation of the ligated tetraaryl-N-heterocyclic carbene and the installation of electron donating groups on the N-aryl substituents is more important than on the C-aryl substituents for effecting catalytic enhancement.

  铱介导的转移氢化反应的催化活性可以通过配位的四芳基N-杂环卡宾的电子变化来轻松调节，而在N-芳基取代基上安装供电子基团对于提升催化效果比在C-芳基取代基上更为重要。
• 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.
• Walther, Dirk; Ritter, Uwe; Kempe, Rhett, Chemische Berichte, 1992, vol. 125, # 7, p. 1529 - 1536
  作者：Walther, Dirk、Ritter, Uwe、Kempe, Rhett、Sieler, Joachim、Undeutsch, Bernd

  DOI：——

  日期：——
• Synthesis of Electronically Diverse Tetraarylimidazolylidene Carbenes via Catalytic Aldimine Coupling
  作者：James W. Ogle、Jubo Zhang、Joseph H. Reibenspies、Khalil A. Abboud、Stephen A. Miller

  DOI：10.1021/ol8012765

  日期：2008.9.1

  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.
• A Novel Decyanogenative Coupling of α-Cyanoimines Mediated by Samarium. A Facile Route to α-Diketimines
  作者：Ashim J. Thakur、Dipak Prajapati、Jagir S. Sandhu

  DOI：10.1246/cl.2004.102

  日期：2004.2

  Conversion of α-cyanoimines 1 into α-diketimines 2 has been achieved successfully by using samarium diiodide in dry tetrahydrofuran in high yields without formation of anilinoanil 3, 1,2-diamines 4 or anilides 5.

  α-氰亚胺1转化为α-二酮亚胺2已成功实现，采用干燥的四氢呋喃中的二碘锶，反应产率高，并且没有生成联苯胺3、1,2-二胺4或酰胺5。

表征谱图