N-(4'-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldimine | 768385-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4'-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldimine
• 英文别名: 4-(5-bromosalicylal)aminobenzo-15-crown-5
• CAS: 768385-52-0
• 化学式: C₂₁H₂₄BrNO₆
• 分子量: 466.329
• InChiKey: FSOAFIKUXZOYCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  29.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.74
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(4'-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldimine 以 甲醇 、 乙醇 、 氯仿 为溶剂， 生成 [ZnLi(H2O)(N-(4'-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldimine(-1H))2]ClO4*H2O
  参考文献：
  名称：

  Synthesis, crystal structure, and vibrational spectrum of lithium N-(4′-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldiminatozinc perchlorate dihydrate

  摘要：

  The synthesis, the IR absorption spectrum, and X-ray diffraction analysis of the complex [ZnLi(L-1)(2)(H2O)](ClO4) center dot H2O (I) (HL1 = N-(4'-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldimine) are described. The crystals of I are monoclinic, a = 19.840(4) angstrom, b = 13.947(3) angstrom, c = 19.956(4) angstrom, beta = 117.06(3)angstrom, V = 4917.4(17) angstrom(3), Z = 4, space group P2(1)/n, R = 0.0609 for 1409 reflections with I > 2 sigma(I). In the complex cation [ZnLi(L-1)(2)(H2O)](+), the Zn atom is bound to a distorted tetrahedral array of two N atoms (av. Zn-N, 2.027(10) angstrom) and two O atoms (av. Zn-O, 1.8968(8) angstrom) of two deprotonated L1 ligands. The Li atom linked to the five ether oxygen atoms (av. Li-O-ether, 2.254(3) angstrom) sits atop the benzo-15-crown-5 (B15C5) macrocyclic plane of one coordinated L-1 ligand. The Li coordination is completed by water oxygen (Li-O(w1), 1.83(5) angstrom). The B15C5 cavity of the second coordinated ligand L1 is vacant.

  DOI：

  10.1134/s0036023607030102
• 作为产物：
  描述：

  4'-氨基苯并-15-冠-5-醚 、 5-溴水杨醛 以 乙醇 为溶剂， 以91%的产率得到N-(4'-benzo-15-crown-5)-5-bromo-2-hydroxyphenylaldimine
  参考文献：
  名称：

  Crown ether-containing N-salicylidene aniline derivatives: synthesis, characterization and optical properties

  摘要：

  15-Crown-5 ether-containing N-salicylidene aniline derivatives of the common formula benzo-15-crown-5-NCH–(2-OH-aryl) [aryl = C6H4 (1), 5-ClC6H3 (2), 5-BrC6H3 (3), C10H6 (4)] have been synthesized and characterized by elemental analysis, NMR, diffuse reflectance, fluorescence, IR and Raman spectroscopies. The crystal structure of 1, elucidated by X-ray diffraction, is stabillized by an intramolecular hydrogen bond and intermolecular π⋯π stacking interactions. Molecules 1–3 are thermochromic and show the presence of a mixture of enol and cis-keto forms in the solid state at room temperature. Compound 1 displays photochromism upon irradiation at 546 nm, which is reversible and exhibits relatively quick back thermal relaxation.

  DOI：

  10.1039/c2ce25600b

文献信息

• Complexing properties of ambidentate benzo-15-crown-5-substituted azomethine ligands
  作者：A. S. Burlov、A. V. Tsukanov、G. S. Borodkin、Yu. V. Revinskii、A. D. Dubonosov、V. A. Bren’、A. D. Garnovskii、A. Yu. Tsivadze、V. I. Minkin

  DOI：10.1134/s1070363206060259

  日期：2006.6

  Crown-containing azomethines and their zinc complexes were prepared. Examination of their structure by H-1 and Li-7 NMR and electronic spectroscopy showed that, in accordance with the concept of hard and soft acids and bases, the hard lithium cation coordinates to the crown ether fragment with the formation of mono- (Li) and binuclear (Li, Zn) complexes.