8-methyl-3-phenylquinoline | 113431-42-8

• 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-3-phenylquinoline
• CAS: 113431-42-8
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: BXIQFMLGTAAIFR-UHFFFAOYSA-N

物化性质

• 沸点：
  373.1±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-3-phenylquinoline 在 dipotassium peroxodisulfate 、 N-乙酰-L-苯丙氨酸 、 sodium acetate 、 palladium diacetate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 8-benzyl-7,9-dioxo-3-phenyl-6b,7,8,9,9a,10-hexahydropyrrolo[3',4':4,5]cyclopenta[1,2-h]quinoline 1-oxide
  参考文献：
  名称：

  8-甲基喹啉氮氧化物的双 C(sp3)–H 和 C(sp2)–H 活化：获得 C7–H 键的途径

  摘要：

  已经完成了 Pd(II) 催化的区域选择性双 C(sp 3 )–H/C7(sp 2 )–H 活化以及 8-甲基喹啉N-氧化物与马来酰亚胺的环化。在 Pd(II) 络合物催化下使用N-氧化物作为弱导向基团可激活初始 C(sp 3 )–H 并触发继发的第二次 C7(sp 2 )–H 激活。双C-H键活化、[3+2]-环化、导向基团的轻松引入和去除、底物范围和官能团多样性是重要的实用特征。

  DOI：

  10.1021/acs.orglett.4c02584
• 作为产物：
  描述：

  7-甲基靛红 在 sodium hydroxide 、 铜 作用下， 反应 3.25h， 生成 8-methyl-3-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

• Aerobic Synthesis of Substituted Quinoline from Aldehyde and Aniline: Copper-Catalyzed Intermolecular C–H Active and C–C Formative Cyclization
  作者：Rulong Yan、Xingxing Liu、Congming Pan、Xiaoqiang Zhou、Xiaoni Li、Xing Kang、Guosheng Huang

  DOI：10.1021/ol402312h

  日期：2013.9.20

  An efficient method for the direct synthesis of substituted quinolines from anilines and aldehydes through C–H functionalization, C–C/C–N bond formation, and C–C bond cleavage has been developed. The method is simple and practical and employs air as an oxidant.

  已经开发了一种通过C–H官能化，C–C / C–N键形成和C–C键裂解从苯胺和醛直接合成取代喹啉的有效方法。该方法简单实用，并采用空气作为氧化剂。
• Cobalt(III)‐Catalyzed, DMSO‐Involved, and TFA‐Controlled Regioselective C−H Functionalization of Anilines with Alkynes for Specific Assembly of 3‐Arylquinolines
  作者：Peiquan Zhang、Yurong Yang、Zhiyong Chen、Zhang Xu、Xuefeng Xu、Zhi Zhou、Xiyong Yu、Wei Yi

  DOI：10.1002/adsc.201801709

  日期：2019.6.18

  Herein, a novel cobalt(III)‐catalyzed and TFA‐controlled [3+2+1] cyclization of diverse anilines and terminal alkynes has been realized by using DMSO as both the solvent and the C1 source, which led to the specific synthesis of privileged 3‐arylquinolines in one pot and regioselectively. Mechanistic investigations revealed that this versatile transformation might be initiated with a C−H activation

  在此，通过使用DMSO作为溶剂和C 1来源，实现了新型的钴（III）催化和TFA控制的各种苯胺和末端炔烃的[3 + 2 + 1]环化反应，这导致了特定的合成在一锅中和区域选择性地排列特权3-芳基喹啉。机理研究表明，这种多用途转化可能是通过CH活化过程和以2-乙烯基苯甲胺类物质为活性中间体而引发的。
• Palladium-Catalyzed C–H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents
  作者：Yimiao He、Lilan Huang、Limei Xie、Peng Liu、Qiongmei Wei、Fangfang Mao、Xuehong Zhang、Jun Huang、Sijing Chen、Chusheng Huang

  DOI：10.1021/acs.joc.9b01278

  日期：2019.8.16

  simple approach for palladium-catalyzed C–H functionalization reactions utilizing an organophosphorus/sulfonate hypervalent iodine reagent as both an oxidant and the source of a functional group has been developed. Through this method, the oxidative phosphorylation-, sulfonation-, and hydroxylation of unactivated benzyl C(sp3)–H bonds, along with the hydroxylation and arylation of aryl C(sp2)–H bonds,

  开发了一种新的且操作简单的方法，该方法利用有机磷/磺酸盐高价碘试剂作为氧化剂和官能团的来源，对钯催化的CH官能化反应进行了开发。通过这种方法，在温和的条件下成功地实现了未活化的苄基C（sp 3）-H键的氧化磷酸化，磺化和羟基化，以及芳基C（sp 2）-H键的羟基化和芳基化。具有出色的站点选择性。通用的C–OSO 2 R键为随后的多样化反应提供了平台。
• 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。
• Lewis acid catalyzed reactivity switch: pseudo three-component annulation of nitrosoarenes and (epoxy)styrenes
  作者：Anisha Purkait、Subhajit Saha、Santanu Ghosh、Chandan K. Jana

  DOI：10.1039/d0cc02650f

  日期：——

  Lewis acid catalyzed alteration of annulation pattern allowed formation of arylquinolines via C–H functionalization of nitrosoarenes and C–C cleavage of (epoxy)styrene.

  Lewis酸催化的环化模式改变允许通过硝基芳烃的C-H官能化和（环氧）苯乙烯的C-C断裂形成芳基喹啉。