N-methyl-N-phenyl-N-(3-quinolyl)amine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-N-phenyl-N-(3-quinolyl)amine
• 英文别名: N-methyl-N-phenylquinolin-3-yl-amine；N-methyl-N-phenylquinolin-3-amine；N-methyl-N-phenyl-3-quinolinamine
• 化学式: C₁₆H₁₄N₂
• 分子量: 234.301
• InChiKey: QFVJJMIRTTUNBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-溴喹啉 、 N-甲基苯胺 在 ClPd[N,N-(2,6-iPr₂C₆H₃)2-4,5-dihydroimidazol-2-yl](cinnamyl) potassium tert-butylate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.5h， 以92%的产率得到N-methyl-N-phenyl-N-(3-quinolyl)amine
  参考文献：
  名称：

  快速室温下使用低催化剂负载量的杂芳族化合物的Buchwald-Hartwig和Suzuki-Miyaura偶联。

  摘要：

  据报道，在室温下，涉及杂芳族卤化物的第二代[（NHC）Pd（R-烯丙基）Cl]络合物用于Suzuki-Miyaura和Buchwald-Hartwig交叉偶联反应。还公开了失活的芳基氯与烯基硼酸的室温Suzuki-Miyaura交叉偶联的第一个实例。钯配合物的烯丙基部分的末端取代促进其在室温下的活化，从而导致非常活跃的催化物质，使得能够使用非常温和的反应条件快速进行本催化转化。Buchwald-Hartwig芳基胺化的催化剂负载量可低至10 ppm，Suzuki-Miyaura反应的催化剂负载量可低至50 ppm。

  DOI：

  10.1002/chem.200600283

文献信息

• Rapid Room Temperature Buchwald–Hartwig and Suzuki–Miyaura Couplings of Heteroaromatic Compounds Employing Low Catalyst Loadings
  作者：Oscar Navarro、Nicolas Marion、Jianguo Mei、Steven P. Nolan

  DOI：10.1002/chem.200600283

  日期：2006.6.23

  complexes for Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions involving heteroaromatic halides at room temperature is reported. The first examples of room temperature Suzuki-Miyaura cross-coupling of deactivated aryl chlorides with alkenyl boronic acids are also disclosed. Terminal substitution at the allyl moiety of the palladium complex facilitates its activation at room temperature leading

  据报道，在室温下，涉及杂芳族卤化物的第二代[（NHC）Pd（R-烯丙基）Cl]络合物用于Suzuki-Miyaura和Buchwald-Hartwig交叉偶联反应。还公开了失活的芳基氯与烯基硼酸的室温Suzuki-Miyaura交叉偶联的第一个实例。钯配合物的烯丙基部分的末端取代促进其在室温下的活化，从而导致非常活跃的催化物质，使得能够使用非常温和的反应条件快速进行本催化转化。Buchwald-Hartwig芳基胺化的催化剂负载量可低至10 ppm，Suzuki-Miyaura反应的催化剂负载量可低至50 ppm。
• (IPr)Pd(acac)Cl:  An Easily Synthesized, Efficient, and Versatile Precatalyst for C−N and C−C Bond Formation
  作者：Nicolas Marion、Elise C. Ecarnot、Oscar Navarro、Dino Amoroso、Andrew Bell、Steven P. Nolan

  DOI：10.1021/jo060190h

  日期：2006.5.1

  and IPr·HCl [acac = acetylacetonate; IPr = N,N‘-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, (IPr)Pd(acac)Cl (1), has proven to be a highly active PdII precatalyst in the Buchwald−Hartwig and the α-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

  从两种市售原料Pd（acac）2和IPr·HCl [acac =乙酰丙酮酸盐；IPr ＝N，已开发出N′-双（2，6-二异丙基苯基）咪唑-2-亚烷基]。所得的络合物（IPr）Pd（acac）Cl（1）已被证明是在Buchwald-Hartwig和α-酮芳基化反应中具有高活性的Pd II预催化剂。已经筛选了多种底物，包括未活化的，位阻的和杂环芳基氯化物。
• Solvent-Free Buchwald-Hartwig Reaction of Aryl and Heteroaryl Halides with Secondary Amines
  作者：Maxim A. Topchiy、Andrey F. Asachenko、Mikhail S. Nechaev

  DOI：10.1002/ejoc.201402077

  日期：2014.6

  A highly efficient solvent-free protocol for the Buchwald–Hartwig amination of (hetero)aryl halides by secondary amines was developed. The reaction is mediated by a Pd(OAc)2/RuPhos catalytic system in air. Various (hetero)aryl halides were coupled with diaryl, alkyl–aryl, and dialkylamines in good to excellent yields (51 examples, 50–99 % yield).

  开发了一种高效的无溶剂方案，用于通过仲胺对（杂）芳基卤化物进行 Buchwald-Hartwig 胺化。该反应由空气中的 Pd(OAc)2/RuPhos 催化系统介导。各种（杂）芳基卤化物与二芳基、烷基-芳基和二烷基胺以良好至极好的产率偶联（51 个实例，产率 50-99%）。
• Diaryl ether condensation reactions
  申请人：——

  公开号：US20030088128A1

  公开（公告）日：2003-05-08

  One aspect of the present invention relates to novel reaction conditions that allow the efficient synthesis of diaryl ethers from arenes bearing a leaving group and arenols under relatively mild conditions. Another aspect of the present invention relates to the dramatic effects of acidic activators on Ullmann-type couplings involving electron-poor and/or relatively insoluble substrates.

  本发明的一个方面涉及新颖的反应条件，允许在相对温和的条件下从带有离去基团的芳烃和芳醇中高效合成二芳基醚。本发明的另一个方面涉及酸性活化剂对涉及电子贫乏和/或相对不溶性底物的乌尔曼型偶合反应的显著影响。
• COMPOUNDS USEFUL FOR TREATING PREMATURE AGING AND IN PARTICULAR PROGERIA
  申请人：Tazi Jamal

  公开号：US20120329796A1

  公开（公告）日：2012-12-27

  The present invention relates to compound (I) wherein: means a pyridazine, a pyrimidine or a pyrazine group, R independently represent a hydrogen atom, a halogen atom or a group chosen among a —CN group, a hydroxyl group, a —COOR 1 group, a (C 1 -C 3 )fluoroalkyl group, a (C 1 -C 3 )fluoroalkoxy group, a —NO2 group, a —NRiR2 group, a (C 1 -C 4 )alkoxy group, a phenoxy group and a (C 1 -C 3 )alkyl group, said alkyl being optionally mono-substituted by a hydroxyl group, n is 1, 2 or 3, n′ is 1 or 2, R′ is a hydrogen atom, a halogen atom or a group chosen among a (Ci-C3)alkyl group, a hydroxyl group, a —COOR 1 group, a —NO2 group, a —NR 1 R 2 group, a morpholinyl or a morpholino group, a N-methylpiperazinyl group, a (Ci-C3)fluoroalkyl group, a (C 1 -C 4 )alkoxy group and a —CN group, Z is N or C, Y is N or C, X is N or C, W is N or C, T is N or C, U is N or C, for use as an agent for preventing, inhibiting or treating pathological or nonpathological conditions linked with premature aging. Some of said compounds are new and also form part of the invention.

  本发明涉及化合物(I)，其中：表示吡啶嗪、嘧啶或吡嗪基团，R独立地表示氢原子、卤素原子或在-CN基团、羟基基团、-COOR1基团、(C1-C3)氟烷基团、(C1-C3)氟烷氧基团、-NO2基团、-NRiR2基团、(C1-C4)烷氧基团、苯氧基团和(C1-C3)烷基团中选择的一种基团，所述烷基可以选择性地被一个羟基基团单取代，n为1、2或3，n'为1或2，R'为氢原子、卤素原子或在(Ci-C3)烷基团、羟基基团、-COOR1基团、-NO2基团、-NR1R2基团、吗啉基或吗啉基团、N-甲基哌嗪基团、(Ci-C3)氟烷基团、(C1-C4)烷氧基团和-CN基团中选择的一种基团，Z为N或C，Y为N或C，X为N或C，W为N或C，T为N或C，U为N或C，用作预防、抑制或治疗与早衰有关的病理或非病理状态的药剂。其中一些化合物是新的，也是本发明的一部分。