4-piperidino-2-phenylnaphtho[2,3-h]quinoline-7,12-dione | 157439-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-piperidino-2-phenylnaphtho[2,3-h]quinoline-7,12-dione
• 英文别名: 2-phenyl-4-(piperidyl-1)-anthra[1,2-b]pyridine-7,12-dione；2-phenyl-4-(piperidyl-1)-pyrido[2,3-a]anthraquinone；2-phenyl-4-piperidino-naphtho{2,3-h}quinoline-7,12-dione；2-phenyl-4-piperidin-1-ylnaphtho[2,3-h]quinoline-7,12-dione
• CAS: 157439-79-7
• 化学式: C₂₈H₂₂N₂O₂
• 分子量: 418.495
• InChiKey: AGLKDJRSKOWFNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-piperidino-2-phenylnaphtho[2,3-h]quinoline-7,12-dione 、 copper(ll) bromide 以 乙醇 为溶剂， 反应 168.5h， 生成 (2-phenyl-4-(piperidyl-1)-anthra[1,2-b]pyridine-7,12-dioneH)2[Cu2Br6]
  参考文献：
  名称：

  Coordination compounds of some d metals with anthrapyridinedione derivatives: Crystal structure of 2-phenyl-4-(piperidyl-1)-anthra[1,2-b]pyridine-7,12-dionium hexabromodicuprate(II) (HL1)2[Cu2Br6]

  摘要：

  Complexes of copper(II), nickel(II), and cobalt(II) chlorides and bromides with 2-phenyl-4-(piperidyl-1)-anthra[1,2-b]pyridine-7,12-dione (L-1) and 2-[phenyl-4-(octylamino)-anthra[1,2-b]pyridine-7,12-dione (L-2) were synthesized from neutral and acidic media. The molecular and crystal structure of 2-phenyl-4-(piperidyl-1)-anthra[1,2-b]pyridine-7,12-dionium hexabromodicuprate(II) (HL1)(2)[Cu2Br6] was determined by X-ray diffraction analysis. The spectral characteristics of L-1 and L-2 and their complexes are presented. Formation of their complexes in solutions was studied.

  DOI：

  10.1134/s0036023612110149
• 作为产物：
  描述：

  1-amino-2-(3-hydroxy-3-phenylprop-1-ynyl)-9,10-anthraquinone 在 硫酸 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 7.5h， 生成 4-piperidino-2-phenylnaphtho[2,3-h]quinoline-7,12-dione
  参考文献：
  名称：

  摘要：

  When heated in piperidine, 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones undergo cyclization into 2-(1-hydroxyalkyl) naphthol 2,3-g]indole-6,11-diones. In contrast, 1-amino-2-(3-hydroxy-3-phenylpropynyl)-9,10-anthraquinone reacts with primary and secondary amines to give the corresponding 1-amino-2-(1-amino-2-benzoylvinyl)-9,10-anthraquinones, which undergo cyclization into 4-dialkylamino- or 4-alkylamino-2-phenylnaphtho[2,3-h]quinoline-7,12-diones. Heating of the starting phenylpropynol with Et3N causes its dehydrogenation and isomerization.

  DOI：

  10.1023/a:1013055106499

文献信息

• The cyclization of vicinal 1-amino-2-acylvinylated derivatives of aromatic amines
  作者：M. S. Shvartsberg、A. V. Piskunov、M. A. Mzhel'skaya、A. A. Moroz

  DOI：10.1007/bf00699931

  日期：1993.8

  A general method for the synthesis of substituted fused polycyclic compounds containing a 4-alkylamino- or 4-dialkylaminopyridine cycle has been proposed. The method includes the addition of primary or secondary amines to vicinal (acylethynyl)arylamines followed by the cyclization of the adducts under acidic or basic catalysis conditions. Various aminonaphthoquinolinediones and aminoquinolines have been prepared in high yields by this method.
• Davydov, V. V.; Sarabia, M. G.; Ezhov, A. I., Russian Journal of Coordination Chemistry, 1994, vol. 20, p. 138 - 143
  作者：Davydov, V. V.、Sarabia, M. G.、Ezhov, A. I.、Sheban, G. V.、Kuznetsov, S. L.、et al.

  DOI：——

  日期：——
• Synthesis and physicochemical properties of the d metal complexes with 2-phenyl-4-(piperidyl-1)-pyrido[2,3-a]anthraquinone. The molecular and crystal structures of 2-phenyl-4-(piperidyl-1)-pyrido[2,3-a]anthraquinonium-7,12 tetranitrozincate
  作者：S. B. Strashnova、B. E. Zaitsev、V. E. Zavodnik、O. V. Kovalchukova、D. P. Voronin

  DOI：10.1134/s1070328407110103

  日期：2007.11

  Two types of complexes of 2-phenyl-4-(piperidyl-1)-pyrido[2,3-a]anthraquinone (L) with transition metals were isolated from neutral acetonitrile and acidified acetonitrile and ethanol solutions and characterized. Metal complexes synthesized at pH = 7 had the composition MCl2L center dot(CH3CN)(n) (M = Cu, Co, Ni). The complexes (HL)(2)[CU2Cl6] (I), (HL)(2)[CoCl4] (II), (HL)(2)[Zn(NO3)(4)] (III) were obtained at pH = 1-2. The molecular and crystal structure ofcomplex III was determined. Some spectral parameters ofL and its complexes were measured.
• ——
  作者：I. I. Barabanov、L. G. Fedenok、N. E. Polyakov、M. S. Shvartsberg

  DOI：10.1023/a:1013055106499

  日期：——

  When heated in piperidine, 1-amino-2-(3-hydroxyalk-1-ynyl)-9,10-anthraquinones undergo cyclization into 2-(1-hydroxyalkyl) naphthol 2,3-g]indole-6,11-diones. In contrast, 1-amino-2-(3-hydroxy-3-phenylpropynyl)-9,10-anthraquinone reacts with primary and secondary amines to give the corresponding 1-amino-2-(1-amino-2-benzoylvinyl)-9,10-anthraquinones, which undergo cyclization into 4-dialkylamino- or 4-alkylamino-2-phenylnaphtho[2,3-h]quinoline-7,12-diones. Heating of the starting phenylpropynol with Et3N causes its dehydrogenation and isomerization.
• Coordination compounds of some d metals with anthrapyridinedione derivatives: Crystal structure of 2-phenyl-4-(piperidyl-1)-anthra[1,2-b]pyridine-7,12-dionium hexabromodicuprate(II) (HL1)2[Cu2Br6]
  作者：S. B. Strashnova、A. B. Ilyukhin、O. V. Koval’chukova、P. V. Strashnov、V. S. Sergienko、B. E. Zaitsev

  DOI：10.1134/s0036023612110149

  日期：2012.11

  Complexes of copper(II), nickel(II), and cobalt(II) chlorides and bromides with 2-phenyl-4-(piperidyl-1)-anthra[1,2-b]pyridine-7,12-dione (L-1) and 2-[phenyl-4-(octylamino)-anthra[1,2-b]pyridine-7,12-dione (L-2) were synthesized from neutral and acidic media. The molecular and crystal structure of 2-phenyl-4-(piperidyl-1)-anthra[1,2-b]pyridine-7,12-dionium hexabromodicuprate(II) (HL1)(2)[Cu2Br6] was determined by X-ray diffraction analysis. The spectral characteristics of L-1 and L-2 and their complexes are presented. Formation of their complexes in solutions was studied.