N,N'-bis-(2-methoxybenzylidene)benzene-1,4-diamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N'-bis-(2-methoxybenzylidene)benzene-1,4-diamine
• 英文别名: N,N'-bis(2-methoxybenzylidene)-p-phenylenediamine
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: TYISIADVNXXHSY-DFEHQXHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.21
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  43.18
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  邻甲氧基苯甲醛 、 对苯二胺 以 乙醇 为溶剂， 反应 2.0h， 以95%的产率得到N,N'-bis-(2-methoxybenzylidene)benzene-1,4-diamine
  参考文献：
  名称：

  N,N‘-Bisbenzylidenebenzene-1,4-diamines and N,N‘-Bisbenzylidenenaphthalene-1,4-diamines as Sirtuin Type 2 (SIRT2) Inhibitors

  摘要：

  A series of N,N'-bisbenzylidenebenzene-1,4-diamine and N,N'-bisbenzylidenenaphthalene-1,4-diamine derivatives were synthesized as inhibitors for human sirtuin type 2 (SIRT2). The design of the new compounds was based on two earlier reported hits from molecular modeling and virtual screening. The most potent compound was N,N'-bis(2-hydroxybenzylidene)benzene-1,4-diamine, which was equipotent with the most potent hit compound and well-known SIRT2 inhibitor sirtinol.

  DOI：

  10.1021/jm060566j

文献信息

• Isomeric Schiff bases related by dual imino-group reversals
  作者：William H. Ojala、Trina M. Arola、Nell Herrera、Barjeta Balidemaj、Charles R. Ojala

  DOI：10.1107/s0108270107006233

  日期：2007.4.15

  Two isomeric pairs of Schiff bases, N,N'-bis(2-methoxybenzylidene)-p-phenylenediamine, C22H20N2O2, (I), and 2,2'-dimethoxy-N,N-(p-phenylenedimethylene)dianiline, C22H20N2O2, (II), and (E,E)-1,4-bis(3-iodophenyl)-2,3-diazabuta-1,3-diene (alternative name: 3-iodobenzaldehyde azine), C14H10I2N2, (III), and N,N'-bis(3-iodophenyl)ethylenediimine, C14H10I2N2 [JAYFEV; Cho, Moore & Wilson (2005). Acta Cryst. E61, o3773-o3774], differ pairwise only in the orientation of their imino linkages and in all four individual cases occupy inversion centers in the crystal, yet all four compounds are found to assume unique packing arrangements. Compounds (I) and (II) differ substantially in molecular conformation, possessing angles between their ring planes of 12.10 (15) and 46.29 (9)degrees, respectively. Compound (III) and JAYFEV are similar to each other in conformation, with angles between their imino linkages and benzene rings of 11.57 (15) and 7.4 (3)degrees, respectively. The crystal structures are distinguished from each other by different packing motifs involving the functional groups. Intermolecular contacts between methoxy groups de ne an R-2(2)(6) motif in (I) but a C(3) motif in (II). Intermolecular contacts are of the I center dot center dot center dot I type in (III), but they are of the N center dot center dot center dot I type in JAYFEV.