2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis(naphthalene-1-carbaldehyde) | 937208-87-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis(naphthalene-1-carbaldehyde)
• 英文别名: 2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)but-2-ene-1,4-diyldioxy]bis(naphthalene-1-carbaldehyde)；2,2'-(2,3-bis((1-formynaphthalen-2-yloxy)methyl)but-2-ene-1,4-diyl)bis(oxy)di-1-naphthaldehyde；2,2',2'',2'''-(1,2-ethenyliden)tetrakis[methylenoxy]tetrakis[1-naphthalinecarbaldehyde]；2-[4-(1-Formylnaphthalen-2-yl)oxy-2,3-bis[(1-formylnaphthalen-2-yl)oxymethyl]but-2-enoxy]naphthalene-1-carbaldehyde；2-[4-(1-formylnaphthalen-2-yl)oxy-2,3-bis[(1-formylnaphthalen-2-yl)oxymethyl]but-2-enoxy]naphthalene-1-carbaldehyde
• CAS: 937208-87-2
• 化学式: C₅₀H₃₆O₈
• 分子量: 764.831
• InChiKey: CNKCHZUVTVAMMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  58
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis(naphthalene-1-carbaldehyde) 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 反应 72.0h， 以96%的产率得到2-({2-({1-[(E)-(hydroxyimino)methyl]-2-naphthyl}-methoxy)-4-({1-[(E)-(hydroxyimino)methyl]-2-naphthyl}oxy)-3-[({1-[(E)-(hydroxyimino)methyl]-2-naphthyl}oxy)methyl]but-2-en-yl}oxy)-1-naphthaldehyde oxime
  参考文献：
  名称：

  Synthesis, characterization and properties of tetra((1-hydroxyimino-methylnaphthalen-2-yloxy)methyl)ethene and its homo-dinuclear metal complexes: A combined experimental and theoretical investigation

  摘要：

  Tetra((1-hydroxyiminomethylnaphthalen-2-yloxy)methyl)ethene (THIMNYOME), H4L, was synthesized by the agents of 2-hydroxy-1-naphtaldehyde, tetra(bromomethyl)ethene and hydroxylamine hydrochloride in two steps. Characterization of THIMNYOME and its dinuclear complexes was made by elemental analyses. IR, H-1- and C-13 NMR, UV-vis, electrospray ionisation mass spectra, molar conductivities and magnetic susceptibility measurements. In the light of these results, it was suggested that the ligand coordinate to each metal atom by the two ether oxygen, two nitrogen atoms of oxime imine (C=N) and an axial oxygen of perchlorate to form pseudo square-pyramidal complexes with Ni(II), Cu(II) and Zn(II). Molar conductivity measurements reveal that all the complexes are non-electrolytes. In addition, the full geometric optimization of the tetraoxime ligand (4) has been made by the B3LYP/6-31G(d) level in order to establish a stable conformation.Additionally, all the complex structures have been studied in the B3LYP/LANL2DZ level. NBO charge distribution and the characteristics of frontier molecular orbitals of these complexes have also been investigated in order to see the electrons movement between ligand and metal atom in the same level. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.07.002
• 作为产物：
  描述：

  1,4-二溴-2,3-双(溴甲基)-2-丁烯 、 2-羟基-1-萘甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis(naphthalene-1-carbaldehyde)
  参考文献：
  名称：

  Synthesis, characterization and properties of tetra((1-hydroxyimino-methylnaphthalen-2-yloxy)methyl)ethene and its homo-dinuclear metal complexes: A combined experimental and theoretical investigation

  摘要：

  Tetra((1-hydroxyiminomethylnaphthalen-2-yloxy)methyl)ethene (THIMNYOME), H4L, was synthesized by the agents of 2-hydroxy-1-naphtaldehyde, tetra(bromomethyl)ethene and hydroxylamine hydrochloride in two steps. Characterization of THIMNYOME and its dinuclear complexes was made by elemental analyses. IR, H-1- and C-13 NMR, UV-vis, electrospray ionisation mass spectra, molar conductivities and magnetic susceptibility measurements. In the light of these results, it was suggested that the ligand coordinate to each metal atom by the two ether oxygen, two nitrogen atoms of oxime imine (C=N) and an axial oxygen of perchlorate to form pseudo square-pyramidal complexes with Ni(II), Cu(II) and Zn(II). Molar conductivity measurements reveal that all the complexes are non-electrolytes. In addition, the full geometric optimization of the tetraoxime ligand (4) has been made by the B3LYP/6-31G(d) level in order to establish a stable conformation.Additionally, all the complex structures have been studied in the B3LYP/LANL2DZ level. NBO charge distribution and the characteristics of frontier molecular orbitals of these complexes have also been investigated in order to see the electrons movement between ligand and metal atom in the same level. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2010.07.002

文献信息

• Binuclear transition metal complexes of a novel lateral N-methylthiosemicarbazone through the central ethylene bridge: Synthesis, structural characterization and the response of ligand molecule to different solvent media
  作者：Mustafa Er、Kemal Sancak、Ismail Değirmencioğlu、Kerim Serbest

  DOI：10.1016/j.molstruc.2007.09.008

  日期：2008.6

  in nature and are of the type 4:1 electrolytes. In Cu(II) and Ni(II) complexes, the environmental effect around the metal ion is in square–planar N 2 S 2 coordination geometry and in Zn(II) complex, is tetrahedral geometry. According to these data, the ligand is found to be chelated to the metal(II) center in its thiolate form through its imine nitrogen and the thiolate sulfur. Additionally, electronic

  摘要 2,2'-(2,3-bis((1-formylnaphthalen-2-yloxy)methyl)but-2-ene-1,4-diyl)bis(oxy)di-1-naphthaldehyde 与 4 -methylthiosemicarbazide 产生了一种新的 N-methylthiosemicarbazone，然后该化合物与 M(ClO 4 ) 2 ·6H 2 O、Cu(II)、Ni(II) 和 Zn(II) 在无水乙醇中反应，产生同双核转变21 元 tetraoxatwelveazatetrathia 大环的金属配合物。通过紫外-可见光、红外、 1 H/ 13 C NMR、质量、元素分析、光谱技术以及摩尔电导率和磁矩数据推断了配体的结构和键合模式以及配合物的整体几何形状。摩尔电导数据表明，Cu(II)、Ni(II) 和 Zn(II) 螯合物本质上是离子型的，属于 4:1 类型的电解质。在
• Studies on synthesis, structure, and DNA cleaving of homo-dinuclear Mn(II), Cu(II), Ni(II), and Zn(II) complexes with a heterocycle-based macroacyclic Schiff base
  作者：Talat Baran、Kaan Karaoğlu、Kerim Serbest、Hülya Ağır、Cemal Sandallı、İsmail Değirmencioğlu

  DOI：10.1007/s00706-013-0926-6

  日期：2013.8

  (E,E',E'',E''')-N,N',N'',N'''-[(1,2-ethenyliden)tetrakis[methylenoxy(2,1-naphthalinediyl)methylidyne]tetrakis[1,2,4-triazol-4-amine] and its novel homo-dinuclear Mn(II), Ni(II), Cu(II), and Zn(II) complexes have been synthesized and characterized by elemental analyses, spectroscopic data (i.e., IR, H-1 and C-13 NMR, UV-Vis), electrospray ionisation mass spectra, XRD, DSC, molar conductivity, and magnetic susceptibility measurements. The absorption bands observed in the electronic spectra and magnetic moment values confirm an octahedral environment around the metal ion. The molar conductivity measurements confirm the non-ionic character of these complexes. The DNA cleavage activities of the Schiff base and its homo-dinuclear complexes are also investigated. Results suggest that all the complexes used can be evaluated as nuclease mimics.

  (E,E',E'',E''')-N,N',N'',N'''-[(1,2-乙二烯基)[2,1-联苯二甲基ynes-甲基氧(2,1-联苯二丁基)的四次苯基甲基配合物]四次[1,2,4-三唑-4-氨基]配合物及其 novel 化学同核 Mn(II), Ni(II), Cu(II) 和 Zn(II) 合成化合物已成功合成并表征。通过元素分析、红外光谱、氢-1 和碳-13 核磁共振光谱、紫外-可见光谱、电雾质谱、X 射线衍射、差示扫描光谱、摩尔电导率和磁性透射测量进行了表征。电电子光谱中的吸收带和磁矩值证实了围绕金属离子的八面体环境。摩尔电导率测量证实这些复合物的非离子特性。 Also, the cleavage activities of the Schiff base and its homodimeric complexes were investigated. Results suggest that all the complexes used can be evaluated as nuclease mimics.
• Synthesis and spectroscopic studies of homo-binuclear, alkoxo bridged homo- and hetero-tetranuclear metal complexes of a bis-N2O4 Schiff base ligand derived from ethanolamine and macroacyclic tetranaphthaldehyde
  作者：Kaan Karaoğlu、Talat Baran、İsmail Değirmencioğlu、Kerim Serbest

  DOI：10.1016/j.saa.2011.03.015

  日期：2011.9

  Three new homo-binuclear Ni(II), Cu(II), Zn(II) complexes (2-4), homo-tetranuclear Cu(II) complex (5), and hetero-tetranuclear Cu(II)-Ni(II) complex (6) of a macroacyclic potentially bis-hexadentate N2O4 Schiff base have been synthesized. The imino-alcohol ligand, H4L was obtained by the condensation of ethanolamine with 2,2'-[2,3-bis(1-formyl-2-naphthyloxymethyl)-but-2-ene-1,4-diyldioxy]bis(naphthalene-1-carbaldehyde). The structures of both the Schiff base and its complexes have been proposed by elemental analyses, spectroscopic data i.e. IR, H-1 and C-13 NMR, UV-vis, electrospray ionisation mass spectra, molar conductivities and magnetic susceptibility measurements. The ligand has two similar compartments to bind first primary two metal ions, and acts bi- or tetra-negative, bis-tetradentate forming five membered chelate ring. However, secondary two metal ions (either Cu2+ or Ni2+.) are ligated with dianionic oxygen atoms of the alcohol groups and are linked to the 1,10-phenanthroline-nitrogen atoms in the tetranuclear complexes (5 and 6). (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis, characterization and properties of tetra((1-hydroxyimino-methylnaphthalen-2-yloxy)methyl)ethene and its homo-dinuclear metal complexes: A combined experimental and theoretical investigation
  作者：Kerim Serbest、Kaan Karaoğlu、Murat Erman、Mustafa Er、İsmail Değirmencioğlu

  DOI：10.1016/j.saa.2010.07.002

  日期：2010.10

  Tetra((1-hydroxyiminomethylnaphthalen-2-yloxy)methyl)ethene (THIMNYOME), H4L, was synthesized by the agents of 2-hydroxy-1-naphtaldehyde, tetra(bromomethyl)ethene and hydroxylamine hydrochloride in two steps. Characterization of THIMNYOME and its dinuclear complexes was made by elemental analyses. IR, H-1- and C-13 NMR, UV-vis, electrospray ionisation mass spectra, molar conductivities and magnetic susceptibility measurements. In the light of these results, it was suggested that the ligand coordinate to each metal atom by the two ether oxygen, two nitrogen atoms of oxime imine (C=N) and an axial oxygen of perchlorate to form pseudo square-pyramidal complexes with Ni(II), Cu(II) and Zn(II). Molar conductivity measurements reveal that all the complexes are non-electrolytes. In addition, the full geometric optimization of the tetraoxime ligand (4) has been made by the B3LYP/6-31G(d) level in order to establish a stable conformation.Additionally, all the complex structures have been studied in the B3LYP/LANL2DZ level. NBO charge distribution and the characteristics of frontier molecular orbitals of these complexes have also been investigated in order to see the electrons movement between ligand and metal atom in the same level. (C) 2010 Elsevier B.V. All rights reserved.