N,N'-methylene-bis(salicylideneamine) | 3923-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N'-methylene-bis(salicylideneamine)
• 英文别名: N,N'-bis(salicylidene)methanediamine；bis(salicylidene)-methylene diamine；methylenebis(N,N'-salicylideneimine)；N,N'-bis(2-hydroxybenzylidene)-1,1-diaminomethane；Bis(salicyliden)-methylendiamin；2-[[(2-hydroxyphenyl)methylideneamino]methyliminomethyl]phenol
• CAS: 3923-68-0
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: AOYHQFWZJWFJGW-UHFFFAOYSA-N

物化性质

• 熔点：
  116-118 °C(Solv: ethanol (64-17-5))
• 沸点：
  419.6±40.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cobalt(II) diacetate tetrahydrate 、 N,N'-methylene-bis(salicylideneamine) 在 N(CH₂CH₃)3 作用下， 以 乙醇 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  双核Co（II）Co（II），Co（II）Co（III）和Co（III）Co（III）的“短”塞伦同系物络合物，由水杨醛和甲二胺或苯甲二胺缩合而得。合成，结构与磁性

  摘要：

  据报道有双核Co（II）Co（II），Co（II）Co（III）和Co（III）Co（III）络合物的双阴离子配体，L 2−，由两摩尔水杨醛或取代的水杨醛，以及1摩尔的 甲二胺 或者 苯基取代的甲二胺。X射线结构和FAB提供了化合物双核性质的直接证据质谱 数据。 氧化作用Co（II）Co（II）配合物[Co 2 L 2 ]与碘的存在下，吡啶，根据L的性质，可生成两种类型的化合物：[Co 2 L 2（py）2 ]（I 3）化学计量的混合价Co（II）Co（III）二聚体（对于苯基甲烷衍生物和完全氧化的Co（III）Co（III）二聚体[Co 2 L 2（py）4 ]（I 3）2，从与甲二胺。[Co 2（salben）2（py）2 ]（I 3）和[Co 2（salmen）2（py）4 ]（I 3）2（salben = N，N'-苯基甲烷二基二苯甲酮 ，salmen = 已经确定了N，N′-甲烷

  DOI：

  10.1039/b105594c
• 作为产物：
  描述：

  聚合甲醛 、 水杨醛 在 硝酸铵 、 三乙胺 作用下， 反应 0.13h， 以90%的产率得到N,N'-methylene-bis(salicylideneamine)
  参考文献：
  名称：

  在无溶剂条件下通过一锅三组分反应高效温和地合成新型席夫碱

  摘要：

  开发了一种简单、高效且经济的方法，通过水杨醛、脂肪醛和脂肪醛的一锅三组分反应合成 N,N'-双（2-羟基亚苄基）-1,1-二氨基烷烃。在无溶剂条件下，室温下，在碱存在下硝酸铵。

  DOI：

  10.1080/10426500802466767

文献信息

• New tetradentate Schiff bases, their oxovanadium(IV) complexes, and some complexes of bidentate Schiff bases with vanadium(III)
  作者：Nosheen Choudhary、David L. Hughes、Uwe Kleinkes、Leslie F. Larkworthy、G.Jeffery Leigh、Michael Maiwald、Celine J. Marmion、J.Roger Sanders、Gallenius W. Smith、Claas Sudbrake

  DOI：10.1016/s0277-5387(96)00436-6

  日期：1997.1

  Abstract New vanadyl(IV) complexes of tetradentate Schiff-base dianions containing one, two or three carbon atoms between the two iminato-nitrogen atoms are described. The compounds are either mononuclear or polymeric, as shown by the value of v(V=O), and depending upon the Schiff-base dianion. There is no evidence for electron delocalization along the polymeric chains. Some vanadium(III) complexes

  摘要描述了在两个亚氨基氮原子之间包含一个，两个或三个碳原子的四齿席夫碱双阴离子新的钒（IV）配合物。这些化合物是单核的或高分子的，如v（V = O）的值所示，具体取决于席夫碱的二价阴离子。没有证据表明电子会沿着聚合物链发生离域化。还分离了一些双齿席夫碱单阴离子钒（III）配合物。报道了[VO（2-OC6H4CHNH）2]的晶体结构和[V（Prhap）3]·甲苯[HPrhap = 2-HOC6H4C（Me）NCH2CH2Me]的结构的初步数据。
• Novel copper(II) complexes of “short” salen homologues. Structure and magnetic properties of the tetranuclear complex [Cu2(L2)2]2 [H2L2 = phenyl-N,N ′-bis(salicylidene)methanediamine] †
  作者：Alessandro Pasini、Francesco Demartin、Olivo Piovesana、Brunetto Chiari、Antonio Cinti、Ornella Crispu

  DOI：10.1039/b003825n

  日期：——

  Copper(II) complexes of Schiff bases derived from the condensation of two molecules of salicylaldehyde and methanediamine (L1) or some phenyl substituted methanediamines (L2–L5) have been synthesized and characterised. The crystal structure of the phenylmethanediamine (L2) derivative has been determined. The ligand acts as bis-bidentate, bridging two copper atoms which are co-ordinated to two phenolato and two imino groups of two ligands. Two binuclear moieties [Cu2(L2)2] are held together through Cu–O(phenolato) interactions between adjacent units forming a pseudo-linear [Cu2L22]2 cluster. Variable temperature magnetic susceptibility data for this derivative reveal the presence of weak antiferromagnetic interactions (−J ≈ 2–3 cm−1) between nearest neighbour spin centres. The structural factors that may be responsible for the sign and magnitude of the exchange interactions are discussed.

  已经合成了由水杨醛和甲二胺（L1）或某些苯基取代的甲二胺（L2-L5）两个分子缩合而成的席夫碱铜（II）配合物，并对其进行了表征。已经确定了苯基甲二胺（L2）衍生物的晶体结构。配体作为双齿状配体，连接两个铜原子，铜原子与两个配体的两个酚基和两个亚氨基基团配位。两个双核部分[Cu2(L2)2]通过相邻单元之间的Cu-O（酚基）相互作用结合在一起，形成伪线性[Cu2L22]2簇。该衍生物的变温磁化率数据表明，最近的相邻自旋中心之间存在弱反铁磁相互作用（△J≅2-3 cm△1）。讨论了可能影响交换相互作用符号和大小的结构性因素。
• Salicylidene-imine-zirconium(IV) complexes in combination with methylalumoxane as catalysts for the conversion of hexa-1,5-diene: adjusting of the catalytic activity
  作者：Bernd Schweder、Dirk Walther、Thomas Döhler、Olaf Klobes、Helmar Görls

  DOI：10.1002/(sici)1521-3897(199911)341:8<736::aid-prac736>3.0.co;2-v

  日期：1999.11

  A variety of substituted Schiff base complexes of the composition ("salen")ZrCl2(thf)(1-21) were synthesized, with methylalumoxane ("MAO") activated and used for a systematic study of their catalytic activity towards hexa-1,5-diene ("salen": substituted salicylidene-ethylene-iminato ligands). Main product of the catalytic cycle is methylenecyclopentane. Dimers are only formed in minor amounts. The catalytic activity and selectivity of the Ziegler-Natta systems strongly depend on the nature and the position of the peripheric substituents in the Schiff base ligands. Electron-withdrawing substituents in para-position to the phenolate oxygen (5-position) decrease the catalytic activity. Improved activity and selectivity were obtained with electron-donating substituents in 5-position. Altering the ethylene bridge causes a lowering of the activity or inactivation. According to the X-ray analysis the metal center in the related complex (L)ZrCl2 (22) (L: N',N'-bis(ethylene)-N'-methyl-N,N"-bis(benzoylacetonatoimine) has a pentagonal-bipyramidal environment. The pentadentate Schiff base Ligand lies in the plane, and both chloro groups occupy the axial positions. In contrast to the catalytically active salene complexes 22 can not rearrange to form a species in which the both chlorides are cis to each other. Consequently 22 is catalytically inactive.
• Diehl, H.; Liggett, L. M.; Hach, C. C., Iowa State College Journal of Science, 1947, vol. 22, p. 110 - 125
  作者：Diehl, H.、Liggett, L. M.、Hach, C. C.、Harrison, G. C.、Henselmeier, L.、et al.

  DOI：——

  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Co: SVol.B1, 93, page 202 - 205
  作者：

  DOI：——

  日期：——