6,8-Di-tert-butyl-3-(2,4-dimethyl-quinolin-7-yl)-3,4-dihydro-2H-benzo[e][1,3]oxazine: Synthesis, Crystal Structure and Luminescent Properties

被引:0
作者
苏清 [1 ]
赵天琦 [1 ]
张杰 [1 ]
李佩 [1 ]
赵晴 [2 ]
叶玲 [3 ]
机构
[1] School of Chemistry, Jilin University
[2] Department of Neurology China-Japan Union Hospital, Jilin University
[3] State Key Laboratory of Supramolecular Structure and Materials, Jilin University
关键词
Mannich reaction; crystal structure; quinoline derivatives; synthesis; luminescent properties;
D O I
10.14102/j.cnki.0254-5861.2014.02.011
中图分类号
O621.13 [];
学科分类号
070303 ; 081704 ;
摘要
6,8-Di-tert-butyl-3-(2,4-dimethyl-quinolin-7-yl)-3,4-dihydro-2H-benzo[e][1,3]oxa- zine(1) was obtained by one-pot reaction starting from 2,4-di-tert-butylphenol, 7-amino-2,4- dimethyl-quinoline and paraformaldehyde. The compound was structurally characterized by NMR, IR and single-crystal X-ray diffraction along with the elemental analysis. Compound 1 crystallizes as solvate with chloroform. The solvate 1·CHCl3(C28 H35 Cl3 N2 O, Mr = 521.93) belongs to the triclinic system, space group P1 with a = 10.852(2), b = 11.352(2), c = 13.050(3), α = 101.95(3), β = 92.94(3), γ = 114.64(3)o, V = 1412.4(5)3, Z = 2, Dc = 1.227 g/cm3, F(000) = 552, μ = 0.347 mm–1, R = 0.0959 and wR = 0.2725(I > 2?(I)). The chloroform molecule displays a rotational disorder as one chloro atom can be located at two different positions. The packing of 1·CHCl3 was further stabilized by intramolecular C–H···O interactions, intermolecular C–H···N interactions, C–H···π interactions, and π···π interactions. The luminescent properties of compound 1 in both methylene chloride solution and the solid state were studied.
引用
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页码:237 / 243
页数:7
相关论文
共 9 条
  • [1] Synthesis and Crystal Structure of a N,N,N′-tri(2-hydroxy-5-methylbenzyl)-1,2-ethanediamine
    王暖升
    汪永涛
    李俊英
    李天铎
    [J]. 结构化学, 2011, 30 (11) : 1533 - 1536
  • [2] 九种Salen型多齿新配体的合成
    王暖升
    汪永涛
    李俊英
    李天铎
    [J]. 有机化学, 2011, 31 (10) : 1703 - 1706
  • [3] Solvent-free Mannich-type reaction of tetraazatricyclododecane (TATD) with phenols[J] . Augusto Rivera,Rodolfo Quevedo.Tetrahedron Letters . 2013
  • [4] Organocatalytic enantioselective multicomponent reactions (OEMCRs)
    Guillena, Gabriela
    Ramon, Diego J.
    Yus, Miguel
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (06) : 693 - 700
  • [5] Phenol derivatized hexahydropyrimidines prepared from Mannich condensations
    Farrell, Joshua R.
    Niconchuk, Jonathan
    Higham, Christine S.
    Bergeron, Brittany W.
    [J]. TETRAHEDRON LETTERS, 2007, 48 (45) : 8034 - 8036
  • [6] Bis-salicylaldiminato zinc complexes: Syntheses, characterization and luminescent properties[J] . Qing Su,Qiao-Lin Wu,Guang-Hua Li,Xiao-Ming Liu,Ying Mu.Polyhedron . 2007 (17)
  • [7] N,N‐Phthaloylamino Acids as Chiral Auxiliaries in Asymmetric Mannich‐Type Reactions[J] . RolandMüller,HelmutGoesmann,HerbertWaldmann.Angewandte Chemie International Edition . 2004 (1‐2)
  • [8] The Synthesis and Selective IL-2 Inhibitory Activity of Bis Piperazine–Phenol Mannich Adducts[J] . Bolin Geng,Paul R Fleming,Scott Umlauf,Augustine Lin,Peter V Pallai.Bioorganic & Medicinal Chemistry Letters . 2002 (5)
  • [9] Mechanical characterization of copolymers based on benzoxazine and epoxy
    Ishida, H
    Allen, DJ
    [J]. POLYMER, 1996, 37 (20) : 4487 - 4495