N,N'-di(m-methoxyphenyl)-1,2-diphenylethane-1,2-diimine | 32349-50-1

• 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'-di(m-methoxyphenyl)-1,2-diphenylethane-1,2-diimine
• 英文别名: N,N'-Di-m-anisylbenzildiimin；N,N'-bis(3-methoxyphenyl)-1,2-diphenylethane-1,2-diimine
• CAS: 32349-50-1
• 化学式: C₂₈H₂₄N₂O₂
• 分子量: 420.511
• InChiKey: OLRFWIGDZYTTSD-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'-di(m-methoxyphenyl)-1,2-diphenylethane-1,2-diimine 在 盐酸 作用下， 反应 14.0h， 生成 联苯甲酰
  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
• 作为产物：
  描述：

  N-benzylidene-m-anisidine 在 氢化镱 、 碘甲烷 、 1-萘甲醛 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 4.0h， 以34%的产率得到N,N'-di(m-methoxyphenyl)-1,2-diphenylethane-1,2-diimine
  参考文献：
  名称：

  A Novel Reductive Dimerization/Oxidative Dehydrogenation of Aldimines Mediated by Lanthanoid Metals

  摘要：

  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.

  DOI：

  10.1021/jo001328d

文献信息

• 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.
• 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。