5,7-dimethyl-3-phenylquinoline | 1373117-76-0

• 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: 5,7-dimethyl-3-phenylquinoline
• 英文别名: 5,7-Dimethyl-3-phenylquinoline
• CAS: 1373117-76-0
• 化学式: C₁₇H₁₅N
• 分子量: 233.313
• InChiKey: MJLAVTIJQDIOPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  氧化苯乙烯 、 1-氨基-3,5-二甲苯 在 iron(III) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以70%的产率得到5,7-dimethyl-3-phenylquinoline
  参考文献：
  名称：

  Iron-Promoted Tandem Reaction of Anilines with Styrene Oxides via C–C Cleavage for the Synthesis of Quinolines

  摘要：

  A novel iron-promoted tandem reaction of anilines with styrene oxides via C-C cleavage and C-H activation has been developed. The reaction utilizes an inexpensive FeCl3 as promoter and is suitable for forming a variety of 3-aryiquinolines from the simple and readily available starting materials.

  DOI：

  10.1021/ol300391t

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。
• 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。
• Substituted quinolines as noncovalent proteasome inhibitors
  作者：Tanner J. McDaniel、Theresa A. Lansdell、Amila A. Dissanayake、Lauren M. Azevedo、Jacob Claes、Aaron L. Odom、Jetze J. Tepe

  DOI：10.1016/j.bmc.2016.04.005

  日期：2016.6

  Screening of a library of diverse heterocyclic scaffolds identified substituted quinolines as inhibitors of the human proteasome. The heterocyclic library was prepared via a novel titanium-catalyzed multicomponent coupling reaction, which rendered a diverse set of isoxazoles, pyrimidines, pyrroles, pyrazoles and quinolines. SAR of the parent lead compound indicated that hydrophobic residues on the

  对不同杂环支架文库的筛选鉴定出取代的喹啉作为人类蛋白酶体的抑制剂。该杂环库是通过一种新型钛催化多组分偶联反应制备的，该反应产生了多种异恶唑、嘧啶、吡咯、吡唑和喹啉。母体先导化合物的 SAR 表明苯并部分上的疏水残基显着提高了效力。先导化合物25抑制蛋白酶体的胰凝乳蛋白酶样蛋白水解活性 (IC 50 5.4 μM)，代表一类新的非肽、非共价蛋白酶体抑制剂。
• QUINOLINE-BASED PROTEASOME INHIBITORS AND USES THEREOF
  申请人：Board of Trustees of Michigan State University

  公开号：US20180282280A1

  公开（公告）日：2018-10-04

  Described herein are quinoline compounds useful for, among other things, inhibition of the proteasome and for treatment of cancer and inflammation.

  本文描述了喹啉化合物，可用于抑制蛋白酶体，治疗癌症和炎症等。