8-(3-chlorophenyl)-6-methylquinoline | 159926-01-9

• 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-(3-chlorophenyl)-6-methylquinoline
• CAS: 159926-01-9
• 化学式: C₁₆H₁₂ClN
• 分子量: 253.731
• InChiKey: ANJPWGFYSPJOLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(3-chlorophenyl)-6-methylquinoline 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 乙醇 、 乌洛托品 作用下， 以 四氯化碳 、 溶剂黄146 为溶剂， 以71%的产率得到8-(3-chlorophenyl)quinoline-6-carbaldehyde
  参考文献：
  名称：

  Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position

  摘要：

  A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivity and selectivity.

  DOI：

  10.1021/ja111670s
• 作为产物：
  描述：

  6-甲基喹啉 、 间氯溴苯 在 dirhodium tetraacetate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以73%的产率得到8-(3-chlorophenyl)-6-methylquinoline
  参考文献：
  名称：

  Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position

  摘要：

  A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivity and selectivity.

  DOI：

  10.1021/ja111670s

文献信息

• QUINOLINES AS TYPE IV PHOSPHODIESTERASE INHIBITORS
  申请人：SYNTEX (U.S.A.) INC.

  公开号：EP0691966A1

  公开（公告）日：1996-01-17
• US5455252A
  申请人：——

  公开号：US5455252A

  公开（公告）日：1995-10-03
• [EN] QUINOLINES AS TYPE IV PHOSPHODIESTERASE INHIBITORS<br/>[FR] QUINOLEINES COMME INHIBITEURS DE LA PHOSPHODIESTERASE TYPE IV
  申请人：SYNTEX (U.S.A.) INC.

  公开号：WO1994022852A1

  公开（公告）日：1994-10-13

  (EN) Optionally 6,8-substituted quinolines of formula (I) wherein: R1 is selected from hydrogen; lower alkyl; cycloalkyl; cycloalkyloxy; cycloalkylamino; cycloalkyl lower alkyl; lower alkoxy; formyl; hydroxy-lower alkyl; carboxyalkyl; optionally substituted aryl, aryloxy, arylamino or aryl lower alkyl; optionally substituted heterocycle, heterocycle-oxy, heterocycle-amino or heterocycle lower alkyl; and R2 is optionally substituted phenyl, or a pharmaceutically acceptable salt or N-oxide thereof, useful as anti-inflammatory agents, immunosuppressive agents, anti-allograft rejection agents, anti-graft-vs-host disease agents, anti-allergic agents (e.g., asthma, rhinitis and atopic dermatitis), bronchodilation agents, anti-autoimmune agents or analgetic agents.(FR) L'invention concerne des 6,8-quinoléines éventuellement substituées de la formule (I). Dans cette formule, R1 est un hydrogène, un alkyle inférieur, un cycloalkyle, un cycloalkyloxy, un cycloalkylamino, un cycloalkylalkyle inférieur, un alcoxy inférieur, un formyle, un hydroxyalkyle inférieur, un carboxyalkyle, un aryle éventuellement substitué, un aryloxy, un arylamino ou un arylalkyle inférieur, un hétérocycle éventuellement substitué, un hétérocycle-oxy, un hétérocycle-amino ou un hétérocycle-alkyle inférieur; et R2 est un phényle, éventuellement substitué. L'invention concerne également les sels de ces quinoléines acceptables sur le plan pharmaceutique ou leurs N-oxydes comme agents anti-inflammatoires, agents immunosuppresseurs, agents pour lutter contre le rejet d'allogreffes, agents contre les réactions du greffon contre l'hôte, agents antiallergiques (par exemple asthme, rhinite, et eczéma atopique), agents bronchodilatateurs, agents contre les affections auto-immunes ou agents analgésiques.
• Rh(NHC)-Catalyzed Direct and Selective Arylation of Quinolines at the 8-Position
  作者：Jaesung Kwak、Min Kim、Sukbok Chang

  DOI：10.1021/ja111670s

  日期：2011.3.23

  A new catalytic protocol for the regioselective direct arylation of quinoline derivatives at the 8-position has been developed. The reaction is catalyzed by a Rh(NHC) system, and the choice of the NHC ligand was most important for achieving high reactivity and selectivity.