6-fluoro-2,3-dimethylquinolin-4-ol | 133767-27-8

• 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: 6-fluoro-2,3-dimethylquinolin-4-ol
• 英文别名: 6-fluoro-2,3-dimethyl-1H-quinolin-4-one
• CAS: 133767-27-8
• 化学式: C₁₁H₁₀FNO
• mdl: MFCD12817472
• 分子量: 191.205
• InChiKey: CUARCPQOSINOMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoro-2,3-dimethylquinolin-4-ol 在 selenium(IV) oxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 8.5h， 生成 4-benzoyloxy-6-fluoro-2-formyl-3-methylquinoline
  参考文献：
  名称：

  Minowa, Nobuto; Imamura, Kei-ichi; Shibahara, Seiji, Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 7, p. 1213 - 1215

  摘要：

  DOI：
• 作为产物：
  描述：

  以 二苯醚 为溶剂， 反应 1.0h， 以0.901 g的产率得到6-fluoro-2,3-dimethylquinolin-4-ol
  参考文献：
  名称：

  Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α_2C-Adrenoceptor Antagonists

  摘要：

  Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human alpha(2)-adrenoceptor subtypes (alpha(2A), alpha(2B), and alpha(2C.)). A number of compounds with good antagonist potencies against the alpha(2C)-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl) phenylamino] quinolin- 3- yl} methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the alpha(2C)-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the alpha(2C)-adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

  DOI：

  10.1021/jm060262x

文献信息

• 4-acyloxyquinoline derivatives and insecticidal or acaricidal
  申请人：Meiji Seika Kabushiki Kaisha

  公开号：US05190952A1

  公开（公告）日：1993-03-02

  A 4-acyloxyquinoline derivative represented by the general formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, a C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.10 cycloalkyl which may be optionally substituted, phenylloweralkyl, phenoxyloweralkyl, aryl group, a group OR.sup.4, where R.sup.4 represents a lower alkyl or aryl group, or a group ##STR2## where X represents an oxygen or a sulphur atom; R.sup.2 represents a hydrogen atom, a lower alkyl alkyl group or a group --COOR.sup.5 where R.sup.5 represents a hydrogen atom or a lower alkyl group; R.sup.3 represents a hydrogen atom, a C.sub.1 -C.sub.10 alkyl or C.sub.2 -C.sub.10 alkenyl group, provided that R.sup.1 does not represent OR.sup.4 when R.sup.2 is a hydrogen atom and R.sup.3 is methyl; R.sup.2 and R.sup.3 together represent a group (CH.sub.2).sub.m, wherein m is 3 or 4, and W represents a hydrogen atom, 1 to 4 halogen atoms, a lower alkyl or lower alkoxy group which may be the same or different and with which the left-hand nucleus is substituted, provided that the compound wherein R.sup.1 represents methyl, R.sup.2, R.sup.3 and W each represent a hydrogen atom is excluded.

  一种由通式（I）表示的4-酰氧基喹啉衍生物：##STR1## 其中R.sup.1表示氢原子，C.sub.1-C.sub.18烷基，C.sub.2-C.sub.18烯基，C.sub.3-C.sub.10环烷基（可以选择性地取代），苯基较低烷基，苯氧基较低烷基，芳基，羟基较低烷氧基，或羟基较低烷氧基，其中R.sup.4表示较低烷基或芳基，或羧基（其中X表示氧或硫原子）; R.sup.2表示氢原子，较低烷基或羧基--COOR.sup.5，其中R.sup.5表示氢原子或较低烷基; R.sup.3表示氢原子，C.sub.1-C.sub.10烷基或C.sub.2-C.sub.10烯基，前提是当R.sup.2为氢原子且R.sup.3为甲基时，R.sup.1不表示OR.sup.4; R.sup.2和R.sup.3一起表示(CH.sub.2).sub.m，其中m为3或4，W表示氢原子，1到4个卤素原子，可以相同或不同的较低烷基或较低烷氧基，用于左侧核取代，其中排除当R.sup.1表示甲基，R.sup.2，R.sup.3和W各表示氢原子的化合物。
• 4-Acyloxyquinoline derivatives and insecticidal or acaricidal compositions containing same
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0407192A2

  公开（公告）日：1991-01-09

  A 4-acyloxyquinoline derivative represented by the general formula (I): wherein R1 represents a hydrogen atom, a C1-C18 alkyl, C2-C18 alkenyl, C3-C10 cycloalkyl which may be optionally substituted, phenylloweralkyl, phenoxyloweralkyl, aryl group, a group OR4, where R4 represents a lower alkyl or aryl group, or a grou p where X represents an oxygen or a sulphur atom; R2 represents a hydrogen atom, a lower alkyl group or a group -COORS where R5 represents a hydrogen atom or a lower alkyl group; R3 represents a hydrogen atom, a C1-C10 alkyl or C2-C10 alkenyl group, provided that R1 does not represent OR4 when R2 is a hydrogen atom and R3 is methyl; R2 and R3 together represent a group (CH2)m, wherein m is 3 or 4, and W represents a hydrogen atom, 1 to 4 halogen atoms, a lower alkyl or lower alkoxy group which may be the same or different and with which the left-hand nucleus is substituted, provided that the compound wherein R1 represents methyl, R2 , R3 and W each represent a hydrogen atom is excluded.

  由通式(I)代表的4-乙酰氧基喹啉衍生物： 其中 R1 代表氢原子、C1-C18 烷基、C2-C18 烯基、可被任选取代的 C3-C10 环烷基、苯基低级烷基、苯氧基低级烷基、芳基、基团 OR4（其中 R4 代表低级烷基或芳基）或基团 X 代表氧原子或硫原子； R2 代表氢原子、低级烷基或基团-COORS（其中 R2 代表低级烷基或芳基）。 其中 X 代表氧原子或硫原子；R2 代表氢原子、低级烷基或基团 -COORS，其中 R5 代表氢原子或低级烷基；R3 代表氢原子、C1-C10 烷基或 C2-C10 烯基，但当 R2 为氢原子且 R3 为甲基时，R1 不代表 OR4；R2 和 R3 共同代表一个基团 (CH2)m，其中 m 为 3 或 4，W 代表氢原子、1 至 4 个卤素原子、低级烷基或低级烷氧基，这些基团可以相同或不同，且左侧核被取代，但 R1 代表甲基、R2、R3 和 W 各代表一个氢原子的化合物除外。
• Use of 4-acyloxyquinoline derivatives as insecticides or acaricides and insecticidal or acaricidal compositions containing the same
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0669321A1

  公开（公告）日：1995-08-30

  The invention relates to use of a 4-acyloxyquinoline derivative represented by the general formula (I): wherein R1 represents hydrogen; alkyl; alkenyl; cycloalkyl which may be optionally substituted; phenyl alkyl; phenyloxy alkyl; phenyl; alkyl and/or halogen-substituted phenyl; naphthyl; alkyl and/or halogen-substituted naphthyl; a group OR4 where R4 represents alkyl, phenyl, alkyl and/or halogen-substituted phenyl, naphthyl, or alkyl and/or halogen-substituted naphthyl; or a group: where X represents an oxygen or a sulphur atom; R2 represents hydrogen; alkyl; or a group -COORs where R5 represents hydrogen or alkyl; R3 represents hydrogen or alkyl; provided that R1 does not represent OR4 when R2 is hydrogen and R3 is methyl; R2 and R3 may together represent -(CH2)m-, where m is 3 or 4; W represents hydrogen, one to four halogen atoms, alkyl or alkoxy which may be same or different and with which the left-hand benzene ring is substituted, proviso that the compound wherein R1 represents methyl, R2, R3 and W each represent a hydrogen atom is excluded for the manufacture of an insecticidal or acaricidal composition. The invention also relates to an insecticidal or acaricidal composition comprising the compound (I) as active ingredient.

  本发明涉及通式 (I) 所代表的 4-乙酰氧基喹啉衍生物的用途： 其中 R1代表氢；烷基；烯基；可任选取代的环烷基；苯基烷基；苯基氧基烷基；苯基；烷基和/或卤素取代的苯基；萘基；烷基和/或卤素取代的萘基；一个基团 OR4，其中 R4 代表烷基、苯基、烷基和/或卤素取代的苯基、萘基或烷基和/或卤素取代的萘基；或一个基团： 其中 X 代表氧原子或硫原子； R2 代表氢；烷基；或基团 -COORs 其中 R5 代表氢或烷基； R3 代表氢或烷基；但当 R2 为氢且 R3 为甲基时，R1 不代表 OR4； R2 和 R3 可共同代表-(CH2)m-，其中 m 为 3 或 4； W代表氢、1至4个卤素原子、烷基或烷氧基，它们可以相同或不同，且左手苯环被其取代，但R1代表甲基，R2、R3和W各代表一个氢原子的化合物不用于制造杀虫或杀螨组合物。本发明还涉及一种杀虫或杀螨组合物，其中包含作为活性成分的化合物 (I)。
• Use of 4-acyloxyquinoline derivatives as insecticides or acaricides
  申请人：MEIJI SEIKA KABUSHIKI KAISHA

  公开号：EP0669321B1

  公开（公告）日：2000-09-27
• US5190952A
  申请人：——

  公开号：US5190952A

  公开（公告）日：1993-03-02