2-methyl-5,7-difluoroquinoline | 256931-39-2

• 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: 2-methyl-5,7-difluoroquinoline
• 英文别名: 5,7-difluoro-2-methylquinoline；5,7-difluoroquinaldine
• CAS: 256931-39-2
• 化学式: C₁₀H₇F₂N
• 分子量: 179.169
• InChiKey: FZFUMSZBFVGHLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-5,7-difluoroquinoline 在 三溴化硼 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丁酮 为溶剂， 生成 5-(2-bromo-ethoxy)-7-fluoro-2-methyl-quinoline
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors

  摘要：

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.031
• 作为产物：
  描述：

  巴豆醛 、 3,5-二氟苯胺 在 乙醚 、 二氯甲烷 、 Sodium sulfate-III 、 silica gel 、 乙酸乙酯 、 正己烷 作用下， 以 盐酸 、 水 为溶剂， 反应 0.5h， 以to give 5,7-difluoro-2-methylquinoline as a brown solid (6.57 g, 44%)的产率得到2-methyl-5,7-difluoroquinoline
  参考文献：
  名称：

  Heterocyclymethylpiperidines and -piperazines possessing affinity at 5ht-1 type receptors

  摘要：

  公开了化学式（I）的化合物及其药用可接受的盐：其中：A是可选取代的苯基、萘基、吲哚基、喹啉基、喹唑啉基、吲唑基、异喹啉基或苯并呋喃基；X是碳，Y是CH且是双键；或X是CH，Y是CH2或氧且是单键；或X是氮，Y是CH2且是单键；R1是卤素、氰基或C1-6烷氧基；a为0、1、2或3；b为0或1；R2是氢、C1-6烷基、C1-6酰基、氟代C1-6酰基、C1-6烷基磺酰基、氟代C1-6烷基磺酰基、氨基甲酰基、C1-6烷基氨基甲酰基或芳基C1-6烷基；R3与其连接的氮原子一起形成一个可选取代的5到7元杂环基固定在苯环上。还公开了制备该化合物的方法以及该化合物在治疗中的用途，特别是用于中枢神经系统紊乱如抑郁症或焦虑症。

  公开号：

  US20050153974A1

文献信息

• Tricyclic compounds
  申请人：——

  公开号：US20030216571A1

  公开（公告）日：2003-11-20

  The present invention is to provide novel tricyclic compounds having leukotriene antagonistic action and represented by the formula: 1 wherein R 1 represents a halogen atom, etc., R 2 represents a nitro group, etc., A represents a 5-membered or a 6-membered heteroaromatic ring group containing 1 to 3 hetero atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, etc., B represents a formula: —OCH 2 —, etc., X represents a sulfur atom, etc., Y represents C 1 -C 10 alkylene group which may have a halogen atom, etc. as a substituent(s), Z represents a carboxyl group whic may be protected, etc., represents a single bond or a double bond, m is an integer of 1 to 4, n is an integer of 1 to 3, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有白三烯拮抗作用的新颖三环化合物，该化合物由下式表示： 1 其中R 1 代表卤素原子等，R 2 代表硝基等，A代表含1至3个杂原子的5元或6元杂芳环基团，杂原子选自由氮原子、氧原子和硫原子等组成的组，B代表公式：—OCH 2 —等，X代表硫原子等，Y代表C 1 -C 10 的烷基链，该烷基链可作为取代基，Z代表可能被保护的羧基等， 代表单键或双键， m是1至4的整数，n是1至3的整数，或其药用可接受的盐。
• [EN] BENZOXAZINONE DERIVATIVES, PREPARATION THEREOF AND USES IN THE TREATMENT OF CNS AND OTHER DISORDERS<br/>[FR] DERIVES DE BENZOXAZINONE, PREPARATION DE CEUX-CI ET UTILISATIONS DE CEUX-CI DANS LE TRAITEMENT DE TROUBLES DU SNC ET D'AUTRES TROUBLES
  申请人：GLAXO GROUP LTD

  公开号：WO2004046124A1

  公开（公告）日：2004-06-03

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed:wherein A, R1, R2, R3, p, q, A and X are as defined in the specification. Preparation of the compounds and uses in the treatment of CNS and other disorders, including depression and anxiety, are also disclosed.

  公开了化合物的公式(I)及其药用盐：其中A、R1、R2、R3、p、q、A和X的定义如规范中所述。还公开了化合物的制备方法以及在治疗中枢神经系统和其他疾病，包括抑郁症和焦虑症中的用途。
• 一种2-一氟甲基喹啉衍生物的制备方法
  申请人：济南大学

  公开号：CN110028447B

  公开（公告）日：2022-10-14

  本发明属于化学合成技术领域，具体涉及一种2‑一氟甲基喹啉衍生物的制备方法。该方法是通过以下步骤实现的：在DMF溶液中，2‑甲基喹啉及其衍生物和Selectfluor反应，通过柱层析后得到一氟代2‑甲基喹啉衍生物。本发明提供的方法在DMF溶液中进行，底物溶解性好、适用性广；反应产率高，可控性强。本发明提供的方法绿色环保，副反应产物少，绿色、高效。
• [EN] HETEROCYCLIC COMPOUNDS POSSESSING AFFINITY AT 5HT1-TYPE RECEPTORS AND USE THEREOF IN THERAPY<br/>[FR] COMPOSES PRESENTANT UNE AFFINITE AVEC DES RECEPTEURS DE TYPE 5HT1 ET LEUR UTILISATION THERAPEUTIQUE
  申请人：GLAXO GROUP LTD

  公开号：WO2003068772A1

  公开（公告）日：2003-08-21

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed:(I)wherein A is optionally substituted phenyl, naphthyl, indolyl, quinolinyl, quinazolinyl, indazolyl, isoquinolinyl or benzofuranyl; b is 1, 2 or 3 and c is 1, 2 or 3, wherein b + c is 2, 3, 4 or 5; X is carbon, Y is CH, is a double bond and e is 0; or X is carbon, Y is CH2 or oxygen, is a single bond and e is 1; or X is nitrogen, Y is CH2, is a single bond and e is 0; R1 is hydrogen, cyano, halogen, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, NHCOCH3 or OCONR5R6, wherein R5 and R6 are independently hydrogen or C1-6alkyl; R2 is halogen, cyano or C1-6alkoxy; d is 0, 1, 2 or 3; R3 is hydrogen, C1-6alkyl, C1-6alkanoyl, fluoroC1-6alkanoyl, C1-6alkylsulfonyl, fluoroC1-6alkylsulfonyl, carbamoyl, C1-6alkylcarbamoyl or arylC1-6alkyl; and R4, together with the nitrogen atom to which it is attached, forms an optionally substituted 5 to 7 membered heterocyclic group fused to the benzene ring, provided that when a compound of formula (I) has the following structure: wherein A, b, c, R1, e, X, Y, R2 and d are as defined above and R3 is hydrogen, C1-6alkyl or arylC1-6alkyl, then (i) X is carbon, Y is CH and is a double bond; or (ii) b and c are both 1; or (iii) the carbon atom adjacent to the oxo-substituted carbon atom in the morpholinyl ring, marked ' * ', is substituted. Methods of preparing the compounds and uses of the compounds in therapy, in particular for a CNS disorder such as depression or anxiety, are also disclosed.

  公开了式(I)的化合物及其药学上可接受的盐： (I)其中A是可选择取代的苯基、萘基、吲哚基、喹啉基、喹唑啉基、吲唑基、异喹啉基或苯并呋喃基；b为1、2或3，c为1、2或3，其中b+c为2、3、4或5；X为碳，Y为CH，为双键，e为0；或X为碳，Y为CH2或氧，为单键，e为1；或X为氮，Y为CH2，为单键，e为0；R1为氢、氰基、卤素、C1-6烷基、C1-6烷氧基、C1-6烷氧基C1-6烷基、NHCOCH3或OCONR5R6，其中R5和R6各自独立地为氢或C1-6烷基；R2为卤素、氰基或C1-6烷氧基；d为0、1、2或3；R3为氢、C1-6烷基、C1-6酰基、氟代C1-6酰基、C1-6烷基磺酰基、氟代C1-6烷基磺酰基、氨基甲酰基、C1-6烷基氨基甲酰基或芳基C1-6烷基；而当式(I)的化合物具有以下结构时：其中A、b、c、R1、e、X、Y、R2和d如上定义，而R3为氢、C1-6烷基或芳基C1-6烷基时，(i) X为碳，Y为CH，为双键；或(ii) b和c均为1；或(iii)在吗啉环中氧代取代的碳原子相邻的碳原子，标记为'*'，被取代。还公开了制备这些化合物的方法以及这些化合物在治疗中的用途，特别是在中枢神经系统紊乱如抑郁症或焦虑症中的用途。
• Heterocyclic compounds possessing affinity at 5ht1-type receptors and use thereof in therapy
  申请人：Harrington P Frank

  公开号：US20050085458A1

  公开（公告）日：2005-04-21

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein A is optionally substituted phenyl, naphthyl, indolyl, quinolinyl, quinazolinyl, indazolyl, isoquinolinyl or benzofuranyl; b is 1, 2 or 3 and c is 1, 2 or 3, wherein b+c is 2, 3, 4 or 5; X is carbon, Y is CH, is a double bond and e is 0; or X is carbon, Y is CH 2 or oxygen, is a single bond and e is 1; or X is nitrogen, Y is CH 2 , is a single bond and e is 0; R1 is hydrogen, cyano, halogen, C 1-6 alkyl, C 1-6 alkoxy, C 1-6 alkoxyC 1-6 alkyl, NHCOCH 3 or OCONR5R6, wherein R5 and R6 are independently hydrogen or C 1-6 alkyl; R2 is halogen, cyano or C 1-6 alkoxy; d is 0, 1, 2 or 3; R3 is hydrogen, C 1-6 alkyl, C 1-6 alkanoyl, fluoroC 1-6 alkanoyl, C 1-6 alkylsulfonyl, fluoroC 1-6 alkylsulfonyl, carbamoyl, C 1-6 alkylcarbamoyl or arylC 1-6 alkyl; and R4, together with the nitrogen atom to which it is attached, forms an optionally substituted 5 to 7 membered heterocyclic group fused to the benzene ring, provided that when a compound of formula (I) has the following structure: wherein A, b, c, R1, e, X, Y, R2 and d are as defined above and R3 is hydrogen, C 1-6 alkyl or arylC 1-6 alkyl, then (i) X is carbon, Y is CH and is a double bond; or (ii) b and c are both 1; or (iii) the carbon atom adjacent to the oxo-substituted carbon atom in the morpholinyl ring, marked “*”, is substituted. Methods of preparing the compounds and uses of the compounds in therapy, in particular for a CNS disorder such as depression or anxiety, are also disclosed.

  公开了式（I）的化合物及其药学上可接受的盐：其中，A是可选择取代的苯基，萘基，吲哚基，喹啉基，喹唑啉基，吲唑基，异喹啉基或苯并呋喃基；b为1、2或3，c为1、2或3，其中b+c为2、3、4或5；X为碳，Y为CH，为双键，e为0；或X为碳，Y为CH2或氧，为单键，e为1；或X为氮，Y为CH2，为单键，e为0；R1为氢、氰、卤素、C1-6烷基、C1-6烷氧基、C1-6烷氧基C1-6烷基、NHCOCH3或OCONR5R6，其中R5和R6独立地为氢或C1-6烷基；R2为卤素、氰或C1-6烷氧基；d为0、1、2或3；R3为氢、C1-6烷基、C1-6酰基、氟代C1-6酰基、C1-6烷基磺酰基、氟代C1-6烷基磺酰基、氨基甲酰基、C1-6烷基氨基甲酰基或芳基C1-6烷基；而R4与其连接的氮原子形成一个可选择取代的5到7元杂环基，与苯环融合，但当式（I）的化合物具有以下结构时，则需满足以下条件：其中，A、b、c、R1、e、X、Y、R2和d如上所定义，而R3为氢、C1-6烷基或芳基C1-6烷基，那么（i）X为碳，Y为CH，为双键；或（ii）b和c均为1；或（iii）在吗啉环中与氧代取代碳原子相邻的碳原子，标记为“*”，被取代。还公开了制备这些化合物的方法以及这些化合物在治疗中的用途，特别是在治疗中枢神经系统疾病如抑郁症或焦虑症中的用途。