5-甲氧基-3-甲基喹啉 | 137595-48-3

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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
• 中文名称: 5-甲氧基-3-甲基喹啉
• 英文名称: 3-Methyl-5-methoxyquinoline
• 英文别名: 5-Methoxy-3-methylquinoline
• CAS: 137595-48-3
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: GUCBSHLSXPWVQU-UHFFFAOYSA-N

物化性质

• 沸点：
  299.4±20.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  5-甲氧基-3-甲基喹啉 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以100 %的产率得到5-methoxy-3-methylquinoline 1-oxide
  参考文献：
  名称：

  Targeting NOX2 with Bivalent Small-Molecule p47phox–p22phox Inhibitors

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c01548
• 作为产物：
  描述：

  N-(3-甲氧基苯基)-2,2-二甲基丙酰胺 在 仲丁基锂 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 17.0h， 生成 5-甲氧基-3-甲基喹啉
  参考文献：
  名称：

  Friedländer Synthesis of Substituted Quinolines from N-Pivaloylanilines

  摘要：

  DOI：

  10.1055/s-1998-2119

文献信息

• A New Modification of the Friedländer Synthesis via <i>ortho</i>-Dilithiated <i>N</i>-Pivaloylanilines
  作者：J. Ubeda、Mercedes Villacampa、Carmen Avendaño

  DOI：10.1055/s-1997-773

  日期：1997.3

  Formylation of ortho-dilithiated N-pivaloylanilines followed by treatment with carbonyl compounds and KHMDS affords 3- or 2,3-substituted quinoline derivatives in a one-pot reaction.

  将正交二锂化的 N-新戊酰基苯胺进行甲酰化，然后用羰基化合物和 KHMDS 进行处理，就能在一锅反应中生成 3 或 2,3 取代的喹啉衍生物。
• Benzoxazinone derivatives, their preparation and use
  申请人：——

  公开号：US20040063704A1

  公开（公告）日：2004-04-01

  The present invention relates to novel compounds of formula (1) or a pharmaceutically acceptable salt thereof, wherein Ar is phenyl, naphthyl, a monocyclic heteroaromatic group or a bicyclic heteroaromatic group, said Ar group being optionally substituted by 1-4 substituents, which may be the same or different, and which are selected from the group consisting of: halogen, hydroxy, cyano, nitro, trifluoromethyl, trifluoromethoxy, C 1-6 alkyl, trifluoromethanesulfonyloxy, pentafluoroethyl, C 1-6 alkoxy, arylC 1-6 alkoxy, C 1-6 alkylthio, C 1-6 alkoxyC 1-6 -alkyl, C 3-7 cycloalkylC 1-6 alkoxy, C 1-6 alkanoyl, C 1-6 alkoxycarbonyl, C 1-6 alkylsulfonyl, C 1-6 alkylsulfinyl, C 1-6 alkylsulfonyloxy, C 1-6 alkylsulfonylC 1-6 alkyl, arylsulfonyl, arylsulfonyloxy, arylsulfonylC 1-6 alkyl, C 1-6 alkylsulfonamido, C 1-6 alkylamido, C 1-6 alkylsulfonamidoC 1-6 alkyl, C 1-6 alkylamidoC 1-6 alkyl, arylsulfonamido, arylcarboxamido, arylsullonamidoC 1-6 alkyl, arylcarboxamidoC 1-6 alkyl, aroyl, arylC 1-6 alkyl, arylC 1-6 alkanoyl, a group R 3 OCO(CH 2 ) s , R 3 CON(R 4 )(CH 2 ) s , R 3 R 4 NCO(C 2 ) s or R 3 R 4 NSO 2 (CH 2 ) where each of R 3 and R 4 independently represents a hydrogen atom or C 1-4 alkyl or R 3 and R 4 form part of a C 1-6 azacyloalkane or C 3- 6 (2-oxo)azacycloalkane ring and s represents zero or an integer from 1 to 4, and a group Ar 1 Z, wherein Z represents a single bond, O, S or CH 2 and Ar 1 represents a phenyl or a monocyclic heteroaromatic group, said Ar 1 group being optionally substituted by 1-3 substituents, which may be the same or different, and which are selected from the group consisting of a halogen, hydroxy, cyano, trifluoromethyl, C 1-6 alkyl, C 1-6 alkoxy or C 1-6 alkanoyl; when Ar is a phenyl or a monocyclic heteroaromatic group, substitutents positioned ortho to one another may be linked to form a 5- or 6-membered ring: R 1 is hydrogen, C 1-6 alkyl, C 3-6 alkenyl, C 3-6 alkynyl or arylC 1-6 alkyl; R 2 is halogen, C 1-6 alkyl, cyano, CF 3 , C 1-6 alkanoyl, C 1-6 alkoxy or hydroxy; X is CH or N; Y is a single bond, O, or C═O; p is 0, 1 or 2; r is 0, 1, 2 or 3; m is 2, 3 or 4; n and q are independently 1 or 2. Processes for preparing the compounds, pharmaceutical compositions containing them and their use as medicaments for various CNS disorders, including deression and/or anxiety, are also disclosed.

  本发明涉及公式（1）的新化合物或其药学上可接受的盐，其中Ar是苯基，萘基，单环杂芳基或双环杂芳基，所述Ar基可以选择性地被1-4个取代基取代，这些取代基可以相同或不同，选自以下群组：卤素，羟基，氰基，硝基，三氟甲基，三氟甲氧基，C1-6烷基，三氟甲磺酰氧基，五氟乙基，C1-6烷氧基，芳基C1-6烷氧基，C1-6烷硫基，C1-6烷氧基C1-6烷基，C3-7环烷基C1-6烷氧基，C1-6酰基，C1-6烷氧羰基，C1-6烷基磺酰基，C1-6烷基亚磺基，C1-6烷基磺酰氧基，C1-6烷基磺酰基C1-6烷基，芳基磺酰基，芳基磺酰氧基，芳基磺酰基C1-6烷基，C1-6烷基磺酰胺基，C1-6烷基酰胺基，C1-6烷基磺酰胺基C1-6烷基，C1-6烷基酰胺基C1-6烷基，芳基磺酰胺基，芳基羧酰胺，芳基磺酰胺基C1-6烷基，芳基羧酰胺基C1-6烷基，酰基，芳基C1-6烷基，芳基C1-6酰基，一个R3OCO（CH2）s，R3CON（R4）（CH2）s，R3R4NCO（C2）s或R3R4NSO2（CH2）组，其中R3和R4各自独立地表示氢原子或C1-4烷基，或R3和R4构成C1-6氮杂环烷或C3-6（2-氧代）氮杂环烷环，s表示零或1-4的整数，以及一个Ar1Z基，其中Z表示单键，O，S或CH2，Ar1表示苯基或单环杂芳基，所述Ar1基可以选择性地被1-3个取代基取代，这些取代基可以相同或不同，选自以下群组：卤素，羟基，氰基，三氟甲基，C1-6烷基，C1-6烷氧基或C1-6酰基；当Ar是苯基或单环杂芳基时，相对位于一个环上的取代基可以连接形成5-或6-成员环；R1是氢，C1-6烷基，C3-6烯基，C3-6炔基或芳基C1-6烷基；R2是卤素，C1-6烷基，氰基，CF3，C1-6酰基，C1-6烷氧基或羟基；X是CH或N；Y是单键，O或C═O；p是0，1或2；r是0，1，2或3；m是2，3或4；n和q独立地为1或2。还公开了制备这些化合物的方法，包含它们的制药组合物以及它们作为治疗各种中枢神经系统疾病，包括抑郁和/或焦虑的药物的用途。
• Synthesis of quinolines via ortho-lithiated N-acylanilines. A modified Friedlaender synthesis
  作者：In Seop Cho、Leyi Gong、Joseph M. Muchowski

  DOI：10.1021/jo00026a019

  日期：1991.12

  A new variation of the Friedlander quinoline synthesis was devised based on the sequential reaction of ortho-lithiated N-t-Boc-anilines or N-pivaloylanilines with masked malondialdehyde derivatives [e.g., vinamidinium salts 1a and 1b, 3-(dimethylamino)acrolein (2), and 3-ethoxymethacrolein (3)] and subsequent acid-induced cyclization.
• BENZOXAZINONE DERIVATIVES, THEIR PREPARATION AND USE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1330460B1

  公开（公告）日：2007-03-21
• US6939871B2
  申请人：——

  公开号：US6939871B2

  公开（公告）日：2005-09-06