N,N'-bis(3-methoxysalicylidene)ethylenediamine | 7396-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N,N'-bis(3-methoxysalicylidene)ethylenediamine
• 英文别名: N,N’-ethylene-bis(3-methoxysalicylaldimine)；N,N'-bis(2-hydroxy-3-Methoxy-benzylidene)ethylenediaMine；2-[2-[(2-hydroxy-3-methoxyphenyl)methylideneamino]ethyliminomethyl]-6-methoxyphenol
• CAS: 7396-77-2
• 化学式: C₁₈H₂₀N₂O₄
• 分子量: 328.368
• InChiKey: POOCDAFRRKDABS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3-methoxysalicylidene)ethylenediamine 在 sodium acetate 作用下， 以 乙醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (N,N'-bis(3-methoxysalicylidene)ethylene-1,2-diamine)platinum(II) monohydrate
  参考文献：
  名称：

  Self‐Assembly of Luminescent Platinum‐Salen Schiff‐Base Complexes

  摘要：

  AbstractTreatment of K2PtCl4 with the MeO‐salen Schiff baseH2L [H2L = N,N′‐bis(3‐methoxysalicylidene)ethylene‐1,2‐diamine] gave the precursor complex PtL, which, upon recrystallization from two different solvent mixtures, afforded different solvate forms of PtL·H2O (1) and PtL·DMF (2) with different solid‐state colors. The self‐assembly of the PtL precursor with K2Pt(CN)4 or K2Pd(CN)4 leads to the isolation of isostructural compound [K2(PtL)2Pt(CN)4]·1.5H2O (3) or [K2(PtL)2Pd(CN)4]·1.5H2O (4), respectively. The solid‐state structures of 1–4 were established by X‐ray crystallography. It is interesting that the helix of the PtL units, along with the other two homochiral helical arrangements of K+ and M2+ (M = Pt or Pd) ions, can generate a unique “fake” example of a triple‐stranded helix in a 1‐D helical polymeric chain. Two such triple‐stranded helical chains intertwining one another can give rise to a double‐stranded helix formed by intermolecular weak C–H···N hydrogen‐bonding interactions with a long helical pitch of ca. 56 Å. The optical absorption and photoluminescence properties of 1–4 were also examined.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

  DOI：

  10.1002/ejic.200700858
• 作为产物：
  描述：

  2-{(E)-[(2-bromoethyl)imino]methyl}-6-methoxyphenol 在 乙醇 、 氨 、 水 作用下， 生成 N,N'-bis(3-methoxysalicylidene)ethylenediamine
  参考文献：
  名称：

  Liggett; Diehl, Iowa State College Journal of Science, 1948, vol. 22, p. 141,146

  摘要：

  DOI：

文献信息

• The coordination chemistry of molybdenum and tungsten. Part XIV. Dioxomolybdenum(VI) complexes of bidentate, tridentate, and tetradentate Schiff bases containing oxygen, nitrogen and sulphur donors
  作者：W.E. Hill、N. Atabay、C.A. McAuliffe、F.P. McCullough、S.M. Razzoki

  DOI：10.1016/s0020-1693(00)93414-5

  日期：1979.1

  bidentate, tridentate, tetradentate Schiff base ligands containing oxygen, nitrogen, and sulphur donor atoms have been complexed to the cis-MoO2 moiety. The structures of the resulting complexes are postulated on the basis of infrared and proton n.m.r. arguments previously developed by Yamada. In the case of the complexes of the tetradentate ligands, the nature of the backbone between the imine groups

  含有氧，氮和硫供体原子的大量二齿，三齿，四齿席夫碱配体已与顺式MoO2部分络合。根据山田先前开发的红外和质子核磁共振理论，推测了所得络合物的结构。在四齿配体的配合物的情况下，亚胺基之间的主链的性质决定了发现哪个顺式异构体。
• Tetranuclear NIR luminescent Schiff-base Zn–Nd complexes
  作者：Xingqiang Lü、Weiyu Bi、Wenli Chai、Jirong Song、Jianxin Meng、Wai-Yeung Wong、Wai-Kwok Wong、Richard A. Jones

  DOI：10.1039/b710204f

  日期：——

  With the simple dinuclear Zn–Nd complex [ZnNdL(H2O)(NO3)3] (1) (H2L = N,N′-bis(3-methoxysalicylidene)ethylene-1,2-diamine) as the precursor, tetranuclear [Zn2Nd2L2(4,4′-bpy)(NO3)6]·Et2O (2) and [Zn2Nd2L2(4,4′-bpe)]·2H2O (3) (4,4′-bpy = 4,4′-bipyridine, 4,4′-bpe = trans-bis(4-pyridyl)ethylene) complexes are formed: suitable choice of bidentate linkers could construct multinuclear heterometallic 3d–4f Schiff-base complexes with improved luminescent properties, and the controlling of linker character shows a potentially effective way to the fine-tuning properties of NIR luminescence from Nd ions.

  以简单的双核Zn–Nd配合物[ZnNdL(H2O)(NO3)3] (1) (H2L = N,N′-双(3-甲氧基水杨醛)亚乙基-1,2-二胺)为前驱体，合成了四核的[Zn2Nd2L2(4,4′-联吡啶)( )6]·Et2O (2)和[Zn2Nd2L2(4,4′-BPE)]·2 (3) (4,4′-联吡啶 = 4,4′-联吡啶，4,4′-BPE = 反式双(4-吡啶基)亚乙基)配合物：适宜的双齿配体的选择可以构建具有增强发光性能的多核异金属3d–4f席夫碱配合物，并且配体性质的调控显示出对来自Nd离子的近红外发光精细调谐的有效途径。
• Zwitterionic Forms of Salicylaldimine Donor Ligands in Unusual Adduct Formation with Organotin(IV) Lewis Acids
  作者：Des Cunningham、Karon Gilligan、Martina Hannon、Cathal Kelly、Pat McArdle、Ann O'Malley

  DOI：10.1021/om030540f

  日期：2004.3.1

  identified). The structural data clearly identify that donor bond formation through the salicylaldimine phenolic oxygen has the concomitant effect of phenolic hydrogen transfer to the imine nitrogen, a process that accounts for the imine hydrolysis which frequently occurs when the salicylaldimine ligands react with Lewis acids. Salicylaldehyde does not assume a zwitterionic form in its 1/1 adduct, F, with

  这项研究的重点是有机锡（IV）路易斯酸与四齿水杨醛亚胺配体H 2 3-MeOsalen [ N，N'-双（3-甲氧基水杨苷）1,2-乙二胺]之间的加合物形成及其后果。和H 2 3-MeOsalbiphen [ N，N′-双（3-甲氧基水杨基吡啶）2，2′-联苯二胺]。SnBu ñ2 Cl 2与H 2 3-MeOsalen反应生成包含悬挂的水杨醛亚胺配体的1/1加合物A，但即使与H 2 3-MeOsalbiphen处于动态平衡状态，也未能与H 2 3-MeOsalbiphen形成固态加合物溶液中的配体。较强的路易斯酸SnPh 2 Cl 2和SnBu nCl 3分别与H 2 3-MeOsalbiphen产生2/1固态加合物D和E，其中每个配体都通过酚和甲氧基氧原子桥接到六个配位的锡中心，并且供体键合。SnBu ñ2（NCS）2与H 2 3-MeOsalen反应，得到加合物B，其结构式为[SnBu
• Third‐Order Nonlinear Optical Properties of DA‐salen‐Type Nickel(II) and Copper(II) Complexes
  作者：João Tedim、Sónia Patrício、Rosa Bessada、Rui Morais、Carla Sousa、Manuel B. Marques、Cristina Freire

  DOI：10.1002/ejic.200600017

  日期：2006.9

  Third-order nonlinear and linear optical properties ofnickel(II) and copper(II) complexes with salen ligands, functionalised with electron donor/acceptor groups (DA-salen), have been investigated in solution by the Z-scan technique using an Nd:YAG laser (λinc = 1064 nm) and UV/Vis spectroscopy. The [M(DA-salen)] complexes exhibit positive nonresonant nonlinear refractive indexes (n2I) in the range27

  用电子供体/受体基团 (DA-salen) 官能化的镍 (II) 和铜 (II) 配合物的三阶非线性和线性光学性质已在溶液中使用 Nd 进行了研究： YAG 激光 (λinc = 1064 nm) 和紫外/可见光谱。[M(DA-salen)] 复合物在 27.0–8.50·10–21 m2 W–1 范围内表现出正的非共振非线性折射率 (n2I) 和在 1.80–26.0·10– 范围内的非线性吸收系数 (α2I) 17 m W–1。后面的值对应于三阶磁化率的总大小的 10% 以下，|χ3|，这是在 λinc = 1064 nm 附近没有电子跃迁的结果。对于 NiIII 配合物组，具有芳香族二亚胺桥和大 π 电子离域的配合物表现出最高的 n2I 值，这导致在 λ = 275-500 nm 区域产生强烈的电子电荷转移带（ϵ > 16000 mol-1 dm3 cm-1）。在 λinc/2 = 532
• Epoxidation of olefins with cationic (salen)manganese(III) complexes. The modulation of catalytic activity by substituents
  作者：K. Srinivasan、P. Michaud、Jay K. Kochi

  DOI：10.1021/ja00269a029

  日期：1986.4

  Augmentation d'activite avec des substituants attracteurs d'electrons (dichloro ou dinitro)

  增强 d'activite avec des substituants 吸引力 d'electrons (dichloro ou dinitro)