2-[(2-(methylamino)ethylimino)methyl]-4-nitrophenol | 1093074-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(2-(methylamino)ethylimino)methyl]-4-nitrophenol
• 英文别名: 2-[2-(Methylamino)ethyliminomethyl]-4-nitrophenol
• CAS: 1093074-50-0
• 化学式: C₁₀H₁₃N₃O₃
• 分子量: 223.232
• InChiKey: IHYOGZYKPLPWBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-(methylamino)ethylimino)methyl]-4-nitrophenol 、 copper(II) acetate monohydrate 以 甲醇 、 水 为溶剂， 以52.2%的产率得到copper(II) (4-nitro-2-[(2-methylaminoethylimino)methyl]phenol)(CH₃COO)
  参考文献：
  名称：

  新型醋酸桥联多核席夫碱铜 (II) 配合物的合成、表征和晶体结构

  摘要：

  合成了一种新型的乙酸桥联多核席夫碱铜 (II) 络合物 [CuL(CH3COO)]n (L=4-nitro-2-[(2-methylaminoethylimino)methyl]phenol)，并通过元素分析对其进行了表征，红外光谱和单晶 X 射线衍射。配合物中的每个Cu原子都是五配位的三角双锥构型，一个亚胺N原子和两个乙酸盐O原子定义基面，一个酚盐O和一个胺N原子占据轴向位置。[4-硝基-2-[(2-甲基氨基乙基亚氨基)甲基]酚基]铜(II)单元通过桥联乙酸盐配体连接，形成沿c轴延伸的聚合物链。

  DOI：

  10.1080/15533170701563947
• 作为产物：
  描述：

  5-硝基水杨醛 、 N-甲基乙二胺 以 甲醇 为溶剂， 以100%的产率得到2-[(2-(methylamino)ethylimino)methyl]-4-nitrophenol
  参考文献：
  名称：

  Synthesis, Crystal Structure and Cytotoxic Property of catena-Poly[[{2-[2-(methylamino)ethyliminomethyl]-4-nitrophenolato}Zinc(II)]-μ-acetato]

  摘要：

  通过元素分析、红外光谱和单晶 X 射线衍射，合成了乙酸根桥聚合物席夫碱锌(II)络合物 [Zn(MENP)(CH3COO)]n（MENP = 2-[2-(甲基氨基)乙基亚氨基甲基]-4-硝基苯酚）。该晶体属于单斜体系，空间群为 P21/c，a = 14.054(2), b = 11.167(1), c = 9.323(2) 埃，β = 92.053(2)°，V = 1462.2(4) 埃3，Z = 4，R 1 = 0.0420，wR 2 = 0.1019。锌原子通过一个希夫碱配体和两个桥接的醋酸阴离子以三棱双锥的方式配位。相邻的 Zn-Zn 间距为 4.727(2) 埃。[Zn(MENP)]单元通过桥接的醋酸基团相连，形成沿 c 轴延伸的链。该复合物对正常细胞和癌细胞都有轻微的细胞毒性。catena-poly[[{2-[2-(methylamino)ethyliminomethyl]-4-nitrophenolato}zinc(II)]-μ-acetato] 的合成、晶体结构和细胞毒性。李文辉通过元素分析、红外光谱和单晶 X 射线衍射，合成了一种新的乙酰基桥接聚合物席夫碱锌(II)配合物。锌原子由一个希夫碱配体和两个桥接的醋酸阴离子以三叉双锥的方式配位。相邻的 Zn-Zn 间距为 4.727(2) 埃。该复合物对正常细胞和癌细胞都有轻微的细胞毒性。

  DOI：

  10.1007/s10870-011-0071-1

文献信息

• Synthesis and characterization of four dicyanamide bridged copper(II) complexes with N2O donor tridentate Schiff bases as blocking ligands
  作者：Prasanta Kumar Bhaumik、Klaus Harms、Shouvik Chattopadhyay

  DOI：10.1016/j.ica.2013.06.025

  日期：2013.8

  Four copper(II) complexes [Cu(L-1)(dca)](n) (1), [Cu(L-2)(dca)(H2O)](2) (2), [Cu(L-3)(dca)](n) (3) and [Cu(L-4)(dca)](n) (4), where HL1 = 2-[(2-aminoethylimino)methyl]-4-nitrophenol, HL2 = 2-[(2-(methylamino)ethylimino)methyl]-4-nitrophenol, HL3 = 2-[(2-(dimethylamino)ethylimino)methyl]-4-nitrophenol and HL4 = 2[(2-(diethylamino)ethylimino)methyl]-4-nitrophenol are tridentate Schiff base ligands, were synthesized and characterized by elemental analysis, IR and UV-Vis spectroscopy and single-crystal X-ray diffraction studies. Complex 1 and 4 are 1D helical, complex 2 is dimeric and complex 3 is 1D linear chain. X-ray single crystal structure analyses reveal that in complexes 1, 2 and 4, dicyanamide (dca) anions act as a purely mu-1,5-bridging ligand whereas in case of complex 3, two consecutive dca units serve as 1,3-bridging ligand while the third one exhibits end-to-end 1,5-bridging mode. Copper(II) centers in case of two complexes (1 and 3) exhibit square pyramidal geometry as depicted by Addison parameter (tau) values whereas metal centers of complexes 2 and 4 depict distorted octahedral and square pyramidal geometry respectively. The role of weak forces like lone pair ... pi/pi...pi interactions in influencing the self-assembly process appears to be of importance. Such types of interactions leading to supramolecular network in the four complexes are described here. (C) 2013 Elsevier B.V. All rights reserved.
• Hydrogen bonding induced lowering of the intra-chain metal–metal distance in single end-on azide bridged one-dimensional copper(II) complexes with tridentate Schiff bases as blocking ligands
  作者：Prasanta Kumar Bhaumik、Klaus Harms、Shouvik Chattopadhyay

  DOI：10.1016/j.poly.2013.10.031

  日期：2014.1

  Three copper(II) complexes, [Cu(L-1)(N-3)]n (1), [Cu(L-2)(N-3)](n)center dot H2O (2) and [Cu(L-3)(N-3)](n) (3) where HL1 = 2-[(2-dimethylamino-ethylimino)-methyl]-4-nitro-phenol, HL2 = 2-[(2-methylamino-ethylimino)-methyl]-4-nitro-phenol and HL3 = 2-[(2-ethylamino-ethylimino)-methyl]-4-nitro-phenol are tridentate Schiff-base ligands}, were prepared and characterized. Single crystal X-ray diffraction studies confirm that each complex is an end-on azide bridged one-dimensional polymer. All the complexes exhibit a square pyramidal geometry around the copper(II) centre. Weak forces like hydrogen bonding interactions lead to various supramolecular architectures. The copper(II)center dot center dot center dot copper(II) distance is minimized by intra chain hydrogen bonding in complex 3. (C) 2013 Elsevier Ltd. All rights reserved.
• Copper(II) complexes with tridentate N2O donor Schiff bases: Modulation of crystalline architectures through supramolecular interactions
  作者：Prasanta Kumar Bhaumik、Klaus Harms、Shouvik Chattopadhyay

  DOI：10.1016/j.poly.2013.08.037

  日期：2014.1

  Three mononuclear copper(11) complexes, [Cu(L-1)(DMF)]ClO4 (1), [Cu(L-2)(DMSO)]ClO4 (2) and [CuL3(NCO)] (3) (where HL1 2-[(2-methylamino-ethylimino)-methyl]-4-nitro-phenol}, HL2 2-[(2-ethylamino-ethylimino)-methyl]-4-nitro-phenol) and HL3 2-[(2-(dimethylamino)ethylimino)methyl]-4-nitrophenol} are tridentate Schiff-base ligands), have been synthesized and characterized by elemental analysis, IR and UV-Vis spectroscopy and single-crystal X-ray diffraction studies. All the complexes are square planar. Complex 1 crystallizes in the triclinic space group P (1) over bar, with cell dimensions a = 8.0396(2), b = 9.0892(2), c= 12.9977(3) angstrom, alpha = 85.591(1)degrees, beta = 84.198(1)degrees and gamma = 76.423(1)degrees, whereas complex 2 crystallizes in the orthorhombic space group, Pbca with cell dimensions a = 8.4615(4), b = 17.2708(11) and c= 25.8517(12) angstrom. Complex 3 crystallizes in the monoclinic space group, P2(1/n) with cell dimensions a = 6.9550(3), b = 13.2257(7), c = 14.7755(6) angstrom and beta = 102.697(3)degrees. Both HL1 and HL2 are capable of forming H bonds due to the presence of H atoms in their amine groups. On the other hand, HL3 cannot form H-bonds. The weak forces like H-bonding, lone pair...pi and pi...pi interactions lead to various supramolecular architectures in the complexes. (C) 2013 Elsevier Ltd. All rights reserved.