Diethyl (2-methyl-6-fluorotetrahydro-quinolin-1-yl)methylenemalonate | 105450-09-7

• 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: Diethyl (2-methyl-6-fluorotetrahydro-quinolin-1-yl)methylenemalonate
• 英文别名: diethyl 2-[(6-fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-yl)methylidene]propanedioate
• CAS: 105450-09-7
• 化学式: C₁₈H₂₂FNO₄
• 分子量: 335.375
• InChiKey: XFDLJNAGQPPZFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  400.3±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl (2-methyl-6-fluorotetrahydro-quinolin-1-yl)methylenemalonate 在 PPA 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以69.1%的产率得到9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis, absolute configuration and intermediates of 9-fluoro-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[i,j]quinolizine-2-carboxylic acid (flumequine)

  摘要：

  The antibacterial agent 9-fluoro-6,7-dihydro-5-methyl- 1-oxo- 1H,5H-benzo[iJ]quinolizine-2-carboxylic acid (flumequine) was synthesized in optically active form from 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ). Racemic FTHQ was resolved with the enantiomers of 3-bromocamphor-8-sulfonic acid. The configurations were established by X-ray structures of the two diastereoisomeric salts. Enantiomeric excesses were determined by H-1 NMR analysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00071-3
• 作为产物：
  描述：

  6-氟-2-甲基喹啉 在 氢气 作用下， 以 甲苯 为溶剂， 120.0~125.0 ℃ 、500.01 kPa 条件下， 反应 26.5h， 生成 Diethyl (2-methyl-6-fluorotetrahydro-quinolin-1-yl)methylenemalonate
  参考文献：
  名称：

  Selective Catalytic Hydrogenation of Heteroarenes with N-Graphene-Modified Cobalt Nanoparticles (Co₃O₄–Co/NGr@α-Al₂O₃)

  摘要：

  Cobalt oxide/cobalt-based nanopartides featuring a core shell structure and nitrogen-doped graphene layers on alumina are obtained by pyrolysis of Co(OAc)(2)/phenanthroline. The resulting core shell material (Co3O4 Co/NGr@alpha-Al2O3) was successfully applied in the catalytic hydrogenation of a variety of N-heteroarenes including quinolines, acridines, benzo[h], and 1,5-naphthyridine as well as unprotected indoles. The peculiar structure of the novel heterogeneous catalyst enables activation of molecular hydrogen at comparably low temperature. Both high activity and selectivity were achieved in these hydrogenation processes, to give important building blocks for bioactive compounds as well as the pharmaceutical industry.

  DOI：

  10.1021/jacs.5b06496

文献信息

• A new organosilylpolyphosphoric reagent, its preparation and application to the process of synthesis of 3-carboxyquinolones or azaquinolones and their salts
  申请人：CENTRO MARGA PARA LA INVESTIGACION S.A.

  公开号：EP0376870A1

  公开（公告）日：1990-07-04

  A process for the preparation of new organosilylpoly­phosphates from the reaction of phosphorus pentoxide with a siloxane or alkyloxysilane to obtain, in solution, reagents the composition of which is [P₂O₅]N[SILANE], where 1 < N < 10 where N is a function of temperatu­re, reaction time and solvent, being applied to the modulation of cyclization reaction of N-susbtituted aminomethylenemalonates leading to quinolones or azaqui­nolones. The N-substituted aminomethylenemalonates are prepared by the reaction of anilines with dialkyl trimethylsilyloxy­methylene-malonates.

  一种制备新的有机硅聚磷酸酯的方法，通过磷五氧化物与硅氧烷或烷氧基硅烷的反应得到溶液中的试剂，其组成为[P₂O₅]N[SILANE]，其中1 < N < 10，N是温度、反应时间和溶剂的函数，用于调节N-取代氨基亚甲基丙二酸酯的环化反应，形成喹啉酮或氮代喹啉酮。N-取代氨基亚甲基丙二酸酯是通过苯胺与二烷基三甲基硅氧基亚甲基丙二酸酯的反应制备的。