8-methyl-6-phenylquinoline | 113431-50-8

• 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: 8-methyl-6-phenylquinoline
• CAS: 113431-50-8
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: LISVAZNETWRSPO-UHFFFAOYSA-N

物化性质

• 沸点：
  365.4±11.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  8-methyl-6-phenylquinoline 在 selenium(IV) oxide 作用下， 生成 6-phenylquinoline-8-carboxylic acid
  参考文献：
  名称：

  Potential antitumor agents. 56. Minimal DNA-intercalating ligands as antitumor drugs: phenylquinoline-8-carboxamides

  摘要：

  A series of isomeric phenylquinoline-8-carboxamides have been synthesized and evaluated as antitumor agents. This configuration is close to the minimum chromophore required for intercalative binding, since the binding mode of the compounds is dependent on the presence and position of the phenyl ring. If the ring is appended at the 4- or 5-position, it cannot lie within the DNA-intercalation site, and the compounds do not intercalate as shown by both unwinding and helix extension assays. In contrast, the 2-, 3-, and 6-phenyl isomers (where the phenyl ring lies coplanar with the quinoline and in the intercalation site) bind by intercalation. Only those isomers that intercalate show in vivo antitumor activity, with the 2-phenyl derivative in particular possessing broad-spectrum activity in both leukemia and solid-tumor assays.

  DOI：

  10.1021/jm00400a029
• 作为产物：
  描述：

  3-甲基-4-硝基联苯 在 盐酸 、 arsenic(V) oxide 、 硫酸 、 铁粉 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 8-methyl-6-phenylquinoline
  参考文献：
  名称：

  Potential antitumor agents. 56. Minimal DNA-intercalating ligands as antitumor drugs: phenylquinoline-8-carboxamides

  摘要：

  A series of isomeric phenylquinoline-8-carboxamides have been synthesized and evaluated as antitumor agents. This configuration is close to the minimum chromophore required for intercalative binding, since the binding mode of the compounds is dependent on the presence and position of the phenyl ring. If the ring is appended at the 4- or 5-position, it cannot lie within the DNA-intercalation site, and the compounds do not intercalate as shown by both unwinding and helix extension assays. In contrast, the 2-, 3-, and 6-phenyl isomers (where the phenyl ring lies coplanar with the quinoline and in the intercalation site) bind by intercalation. Only those isomers that intercalate show in vivo antitumor activity, with the 2-phenyl derivative in particular possessing broad-spectrum activity in both leukemia and solid-tumor assays.

  DOI：

  10.1021/jm00400a029

文献信息

• Cp*Co(III)-Catalyzed C(sp³)–H Bond Activation: A Highly Stereoselective and Regioselective Alkenylation of 8-Methylquinoline with Alkynes
  作者：Malay Sen、Balakumar Emayavaramban、Nagaraju Barsu、J. Richard Premkumar、Basker Sundararaju

  DOI：10.1021/acscatal.6b00612

  日期：2016.5.6

  Efficient, atom-economical, highly regioselective C(sp3)–H bond alkenylation of 8-methylquinoline catalyzed by (Cp*)Co(III) is reported. A well-defined, air-stable, molecular cobalt catalyst, Cp*Co(III), is employed for the first time in C(sp3)–H bond activation. The developed methodology is broadly applicable and tolerates a variety of functional groups, under mild conditions. Experimental and density

  报道了由（Cp *）Co（III）催化的高效的，原子经济的，高度区域选择性的C（sp 3）–H键的8-甲基喹啉C链烯基化反应。定义明确的，空气稳定的分子钴催化剂Cp * Co（III）首次用于C（sp 3）–H键活化。所开发的方法具有广泛的适用性，并且在温和的条件下可以耐受各种官能团。实验和密度泛函理论（DFT）结果表明，最初的环金属化是通过外部碱基辅助的协同金属化去质子化途径发生的。
• Palladium(<scp>ii</scp>)-catalyzed oxidative C(sp³)–P bond formation <i>via</i> C(sp³)–H bond activation
  作者：Lijin Chen、Zhenfei Zhou、Saifei Zhang、Xiaoqian Li、Xuebing Ma、Jiaxing Dong

  DOI：10.1039/c9cc07637a

  日期：——

  Disclosed herein is a Pd(II)-catalyzed C(sp3)–H/P–H oxidative cross-coupling reaction between 8-methylquinolines with H-phosphonates or diarylphosphine oxides via chelation-assisted C(sp3)–H bond activation. The protocol exhibits a relatively broad functional-group tolerance and exclusive chemo- and regioselectivity. Furthermore, detailed mechanistic studies support the proposed reaction pathway.

  本文公开了通过螯合辅助的C（sp 3）-H键活化作用，Pd（II）催化的8-甲基喹啉与H-膦酸酯或二芳基膦氧化物之间的Pd（II）催化的C（sp 3）-H / P-H氧化交叉偶联反应。。该协议表现出相对广泛的功能组耐受性和排他性的化学和区域选择性。此外，详细的机理研究支持所提出的反应途径。
• Cp*Co^III-Catalyzed C(sp³)−H Bond Amidation of 8-Methylquinoline
  作者：Nagaraju Barsu、Md. Atiur Rahman、Malay Sen、Basker Sundararaju

  DOI：10.1002/chem.201601597

  日期：2016.6.27

  An efficient and external oxidant‐free, Cp*CoIII‐catalyzed C(sp3)−H bond amidation of 8‐methylquinoline, using oxazolone as an efficient amidating agent, is reported for the first time under mild conditions. The reaction is selective and tolerates a variety of functional groups. Based on previous reports and experimental results, the deprotonation pathway proceeds through an external base‐assisted

  首次在温和的条件下报道了使用恶唑酮作为高效酰胺化剂的高效且无外部氧化剂，Cp * Co III催化的8-甲基喹啉的C（sp 3）-H键酰胺化反应。该反应是选择性的，并且可以耐受多种官能团。根据以前的报道和实验结果，去质子化途径是通过外部碱辅助的协同金属化和去质子化过程进行的。
• Cobalt(III)-Catalyzed Alkylation of Primary C(<i>sp</i> ³ )-H Bonds with Diazo Compounds
  作者：Sheng-Yi Yan、Peng-Xiang Ling、Bing-Feng Shi

  DOI：10.1002/adsc.201700636

  日期：2017.9.4

  challenge. Here we report the first cobalt(III)-catalyzed alkylation of 8-methylquinolines with diazo compounds through primary C(sp3)–H cobaltation/carbenoid insertion. The reaction is highly efficient, scalable and tolerates a variety of functional groups. Furthermore, the unique protocol can be applied to the synthesis of azatricyclic antibiotic compounds.

  螯合辅助的C（sp 2）–H金属化/类胡萝卜素插入已得到充分研究。然而，C（sp 3）–H键的类似卡宾官能化仍然是一个巨大的挑战。在这里，我们报告了通过重载C（sp 3）-H钴/类胡萝卜素与重氮化合物的首次由钴（III）催化的8-甲基喹啉与重氮化合物的烷基化反应。该反应是高效的，可扩展的并且耐受多种官能团。此外，该独特的方案可以应用于氮三环抗生素化合物的合成。
• Switchable, Reagent-Controlled C(sp³)-H Selective Iodination and Acetoxylation of 8-Methylquinolines
  作者：Ming-Lu Zhang、Xing-Long Zhang、Rui-Li Guo、Meng-Yue Wang、Bao-Yin Zhao、Jin-Hui Yang、Qiong Jia、Yong-Qiang Wang

  DOI：10.1021/acs.joc.2c00076

  日期：2022.5.6

  Pd-catalyzed C(sp3)-H selective iodination of 8-methylquinolines is reported herein for the first time. Because of the versatility of organic iodides, the method offers a facile access to various C8-substituted quinolines. By slightly switching the reaction conditions, an efficient C(sp3)-H acetoxylation of 8-methylquinolines has also been enabled. Both approaches feature mild reaction conditions, good tolerance

  本文首次报道了一种高效的 Pd 催化 C(sp 3 )-H 选择性碘化 8-甲基喹啉。由于有机碘化物的多功能性，该方法提供了一种容易获得各种 C8 取代的喹啉的方法。通过稍微改变反应条件，8-甲基喹啉的有效C(sp 3 )-H 乙酰氧基化也成为可能。这两种方法都具有反应条件温和、官能团耐受性好、底物范围广等特点。