N,N-dimethyl-4-(4-methylquinolin-2-yl)aniline | 863487-47-2

• 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: N,N-dimethyl-4-(4-methylquinolin-2-yl)aniline
• 英文别名: N,N-dimethyl-4-(4-methyl-2-quinolyl)aniline；2-(4-dimethylaminophenyl)-4-methylquinoline；N,N-dimethyl-4-(4-methylquinolin-2-yl)benzenamine
• CAS: 863487-47-2
• 化学式: C₁₈H₁₈N₂
• 分子量: 262.354
• InChiKey: XFENQZYOYKXDEN-UHFFFAOYSA-N

物化性质

• 沸点：
  426.9±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 N,N-dimethyl-4-(4-methylquinolin-2-yl)aniline 以 乙二醇乙醚 、 水 为溶剂， 生成 [ClPt(N,N-dimethyl-4-(4-methylquinolin-2-yl)aniline(-1H))]2
  参考文献：
  名称：

  亮氨酸基配体的环金属化铂（II）络合物作为高效电致发光剂

  摘要：

  一系列新的含lepidine-配体为基础的环金属化铂（II）配合物1 - 7与通式[PT（L）ACAC]（L =基于lepidine配体，ACAC =乙酰丙酮化物）已经被合成。配合物已使用光谱和电化学技术进行了表征。配合物2和5的单晶X射线结构已成功确定。讨论了取代基对配合物环金属化苯环的电子特征和氧化还原电势的影响。配合1 - 7在液体和固态中均具有高磷光性，覆盖从黄色到饱和红色的相当宽的光谱范围。这些配合物已成功用作掺杂材料，以制造电致发光器件，ITO / NPB（40 nm）/掺杂CBP的Pt配合物（5 wt％）（20 nm）/ BCP（10 nm）/ Alq 3（20 nm） / LiF（1 nm）/ Al（150 nm），表现出非常有前途的性能。掺杂有5 wt％3的器件产生的最大外部量子效率为15.2％，最大亮度为26847 cd m -2，对应的发光效率为29.83 cd A -1。

  DOI：

  10.1021/om100573r
• 作为产物：
  描述：

  4-甲基-2-氯-喹啉 、 4-(N,N-二甲基)苯胺溴化镁 在 C₃₂H₂₆ClN₂NiP 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以99%的产率得到N,N-dimethyl-4-(4-methylquinolin-2-yl)aniline
  参考文献：
  名称：

  Amido Pincer Nickel Catalyzed Kumada Cross-Coupling of Aryl, Heteroaryl, and Vinyl Chlorides

  摘要：

  Amido pincer nickel complexes {Ni(Cl)[2-P(Ph-2)C6H4NC(Ph)=NAr]} (Ar = 4-MeC6H4, 1; Ar = 4-ClC6H4, 2; Ar = 4-MeOC6H4, 3) were shown to efficiently catalyze the cross-coupling of activated, unactivated, and deactivated aryl chlorides, N-heteroaryl chlorides, 1,4-dichlorobenzene, and vinyl chlorides with aryl Grignard reagents.

  DOI：

  10.1055/s-0033-1339653

文献信息

• Carbocatalytic Cascade Synthesis of Polysubstituted Quinolines from Aldehydes and 2‐Vinyl Anilines
  作者：Mikko K. Mäkelä、Evgeny Bulatov、Kiia Malinen、Juulia Talvitie、Martin Nieger、Michele Melchionna、Anna Lenarda、Tao Hu、Tom Wirtanen、Juho Helaja

  DOI：10.1002/adsc.202100711

  日期：2021.8.3

  polysubstituted quinolines from o-vinyl anilines and aldehydes. The reaction proceeds in a cascade manner through condensation, electrocyclization and dehydrogenation, and gives access to a wide range of quinolines with alkyl and/or aryl substituents as demonstrated with 40 examples. The metal-free catalytic procedure allows a heterogeneous protocol for the synthesis of various polysubstituted quinolines. The

  氧化活性炭 (oAC) 催化邻乙烯基苯胺和醛形成多取代喹啉。该反应通过缩合、电环化和脱氢以级联方式进行，并提供了范围广泛的具有烷基和/或芳基取代基的喹啉，如 40 个例子所示。无金属催化过程允许合成各种多取代喹啉的异质协议。机理研究表明，oAC 中的酸基和醌基都是催化歧管的组成部分。
• Nickel complexes supported by quinoline-based ligands: synthesis, characterization and catalysis in the cross-coupling of arylzinc reagents and aryl chlorides or aryltrimethylammonium salts
  作者：Qiang Zhang、Xue-Qi Zhang、Zhong-Xia Wang

  DOI：10.1039/c2dt30886j

  日期：——

  Lithium and nickel complexes bearing quinoline-based ligands have been synthesized and characterized. Reaction of 8-azidoquinoline with Ph2PNHR (R = p-MeC6H4, But) affords N-(8-quinolyl)iminophosphoranes RNHP(Ph2)N(8-C9H6N) (1a, R = p-MeC6H4; 1b, R = But. C9H6N = quinolyl)). Reaction of 1a with (DME)NiCl2 generates a nickel complex [NiCl2N(8-C9H6N)P(Ph2)NH(p-MeC6H4)}] (2a). Treatment of 1b with (DME)NiCl2 and following with NaH produces [NiCl(1,2-C6H4)P(Ph)(NHBut)N(8-C9H6N)}] (4). Complex 4 was also obtained by reaction of (DME)NiCl2 with [Li(1,2-C6H4)P(Ph)(NHBut)N(8-C9H6N)}] (5) prepared through lithiation of 1b. Reaction of 2-PyCH2P(Ph2)N(8-C9H6N) (6, Py = pyridyl) and PhNC(Ph)CH2P(Ph2)N(8-C9H6N) (8), respectively, with (DME)NiCl2 yields two five-coordinate N,N,N-chelate nickel complexes, [NiCl22-PyCH2P(Ph2)N(8-C9H6N)}] (7) and [NiCl2PhNC(Ph)CH2P(Ph2)N(8-C9H6N)}] (9). Similar reaction between Ph2PCH2P(Ph2)N(8-C9H6N) (10) and (DME)NiCl2 results in five-coordinate N,N,P-chelate nickel complex [NiCl2Ph2PCH2P(Ph2)N(8-C9H6N)}] (11). Treatment of [(8-C9H6N)NP(Ph2)]2CH2 (12) [prepared from (Ph2P)2CH2 and 2 equiv. of 8-azidoquinoline] with LiBun and (DME)NiCl2 successively affords [NiCl(8-C9H6N)NP(Ph2)}2CH] (13). The new compounds were characterized by 1H, 13C and 31P NMR spectroscopy (for the diamagnetic compounds), IR spectroscopy (for the nickel complexes) and elemental analysis. Complexes 2a, 4, 7, 9, 11 and 13 were also characterized by single-crystal X-ray diffraction techniques. The nickel complexes were evaluated for the catalysis in the cross-coupling reactions of arylzinc reagents with aryl chlorides and aryltrimethylammonium salts. Complex 7 exhibits the highest activity among the complexes in catalyzing the reactions of arylzinc reagents with either aryl chlorides or aryltrimethylammonium bromides.

  含喹啉基配体的锂和镍配合物已被合成和表征。8-叠氮喹啉与Ph2PNHR(R = p-Me , But)反应得到N-(8-喹啉基)亚氨基膦烷RNHP(Ph2)N(8-C9H6N)(1a, R = p-Me ; 1b, R = But. = 喹啉基))。1a与(DME)NiCl2反应生成镍配合物[NiCl2N(8- )P(Ph2)NH(p-Me )}] (2a)。1b与(DME)NiCl2反应后，再用NaH处理得到[NiCl(1,2-C6H4)P(Ph)(NHBut)N(8- )}] (4)。配合物4也可通过(DME)NiCl2与[Li(1,2- )P(Ph)(NHBut)N(8- )}] (5)反应得到，后者是通过1b的锂化制备的。2-吡啶基甲基P(Ph2)N(8- )(6, Py = 吡啶基)和PhNC(Ph)CH2P(Ph2)N(8- )(8)分别与(DME)NiCl2反应，得到两个五配位的N,N,N-螯合镍配合物[NiCl22-Py (Ph2)N(8- )}] (7)和[NiCl2PhNC(Ph) (Ph2)N(8- )}] (9)。Ph2PCH2P(Ph2)N(8- )(10)与(DME)NiCl2的类似反应生成五配位的N,N,P-螯合镍配合物[NiCl2Ph2PC (Ph2)N(8- )}] (11)。[(8- )NP(Ph2)]2CH2(12)[由(Ph2P)2CH2和2当量的8-叠氮喹啉制备]依次与LiBun和(DME)NiCl2反应得到[NiCl(8- )NP(Ph2)}2CH] (13)。新化合物通过1H、13C和31P NMR光谱(对于抗磁性化合物)、IR光谱(对于镍配合物)和元素分析进行表征。配合物2a、4、7、9、11和13还通过单晶X射线衍射技术进行表征。这些镍配合物被评估用于芳基锌试剂与芳基氯和芳基三甲基铵盐的交叉偶联反应的催化活性。在催化芳基锌试剂与芳基氯或芳基三甲基溴化铵的反应中，配合物7显示出最高的活性。
• Synthesis and electroluminescent property of highly efficient phosphorescent red dopants based on modulated main ligands
  作者：Seo Yun Lee、Song Eun Lee、Ye Na Oh、Young Kwan Kim、Dong Myung Shin

  DOI：10.1080/15421406.2017.1350041

  日期：2017.8.13

  Novel red phosphorescent iridium(III) complexes, (DPAP-MQ)(2)Ir(tmd), (DMAP-MQ)(2)Ir(tmd), (PN-MQ)(2)Ir(tmd) were synthesized for red emitter of the phosphorescent organic light-emitting diodes (phOLEDs). The ligands have sites of both the electron donor and acceptor in a molecule. The main ligands consisted of electron-donors ((dimethylamino)phenyl, (diphenylamino)phenyl, (dimethylamino)naphthalene) and electron-acceptor methyl quinoline were synthesized by suzuki coupling reaction. The iridium(III) complexes based on main ligands and 2,2,6,6-tetramethyl-3,5-heptanedione(tmd) ancillary ligand were synthesized by Nonoyama reaction. Their luminescence property was investigated by UV-visible spectroscopy and photoluminescence (PL) spectroscopy. The manufactured PHOLEDs were characterized by investigation of current density-voltage-luminance, luminance efficiency, external quantum efficiency, electroluminescence spectrum. These phosphorescent iridium complexes will be promising candidates for highly efficient red emitters.
• Efficient Red-Emitting Cyclometalated Iridium(III) Complexes Containing Lepidine-Based Ligands
  作者：K. R. Justin Thomas、Marappan Velusamy、Jiann T. Lin、Chin-Hsiung Chien、Yu-Tai Tao、Yuh S. Wen、Ya-Hui Hu、Pi-Tai Chou

  DOI：10.1021/ic050385s

  日期：2005.8.1

  Heteroleptic cyclometalated iridium(III) complexes featuring lepidine-based ligands and acetyl acetone auxiliary ligand are synthesized. Multiple lowest energy absorption bands are observed for these complexes indicating substantial mixing of the singlet and triplet levels. All the complexes emit orange or red color in dichloromethane solutions with lifetimes in the range 1.6-3.7 mu s. The emission in the complexes probably originates from the (MLCT)-M-3 state. The complexes are applied as emitting guests in LED devices of the structure ITO/HTL(BPAPF or NPB)/6% Ir in CBP/BCP/Alq(3)LiF/Al. They exhibit excellent device characteristics with an orange to red EL profile.