ethyl 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate | 1239164-76-1

• 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: ethyl 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate
• 英文别名: ethyl 1-methyl-2-oxoquinoline-3-carboxylate
• CAS: 1239164-76-1
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: BSVJRLROVPUTMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate 在 lithium hydroxide monohydrate 、 水 、 柠檬酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以96%的产率得到1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  RING-FUSED 2-PYRIDONE DERIVATIVES AND HERBICIDES

  摘要：

  提供了具有优异除草活性并对有用作物等表现出高安全性的2-吡啶酮衍生物；其盐；以及含有这些化合物的除草剂。更详细地说，提供了通式[I]所表示的2-吡啶酮衍生物或其农药可接受的盐，以及含有这些化合物的除草剂。在通式[I]中，X1是氧原子或硫原子；X2、X3和X4分别为CH或N(O)m；m是0或1的整数；R1是氢原子，C1-12烷基或类似物；R2是卤素原子，氰基或类似物；n是0到4的整数；R3是羟基，卤素原子或类似物；A1是C(R11R12)；A2是C(R13R14)或C═O；A3是C(R15R16)；R11、R12、R13、R14、R15和R16分别独立地是氢原子或C1-6烷基基团。

  公开号：

  US20110287937A1
• 作为产物：
  描述：

  2-[(2-硝基苯基)亚甲基]丙二酸二乙基酯 在 铁粉 、 potassium carbonate 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 0.5h， 生成 ethyl 1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  香豆素-3-羧化物与丙烯酰胺类似物之间的可见光驱动的分子间[2 + 2]环加成反应

  摘要：

  本文报道了室温下可见光驱动的协议，涉及通过能量转移过程在香豆素-3-羧酸酯和丙烯酰胺类似物之间的分子间[2 + 2]环加成反应。使用铱配合物FIrPic作为光敏剂，并使用3 W蓝色LED作为光源，以中等到极好的收率制备了一系列的环丁苯并苯并吡喃酮。

  DOI：

  10.1002/chem.201501176

文献信息

• RING-FUSED 2-PYRIDONE DERIVATIVES AND HERBICIDES
  申请人：Takabe Fumiaki

  公开号：US20110287937A1

  公开（公告）日：2011-11-24

  Provided are 2-pyridone derivatives which have excellent herbicidal activity and exhibit high safety to useful crops and so on; salts thereof; and herbicides containing same. In more detail, 2-pyridone derivatives represented by general formula [I] or agrochemically acceptable salts thereof, and herbicides containing these compounds are provided. In general formula [I], X 1 is an oxygen atom or a sulfur atom; X 2 , X 3 , and X 4 are to each CH or N(O) m ; m is an integer of 0 or 1; R 1 is a hydrogen atom, a C 1-12 alkyl group, or the like; R 2 is a halogen atom, a cyano group, or the like; n is an integer of 0 to 4; R 3 is a hydroxyl group, a halogen atom, or the like; A 1 is C(R 11 R 12 ); A 2 is C(R 13 R 14 ) or C═O; A 3 is C(R 15 R 16 ); and R 11 , R 12 , R 13 , R 14 , R 15 , and R 16 are each independently a hydrogen atom or a C 1-6 alkyl group.

  提供了具有优异除草活性并对有用作物等表现出高安全性的2-吡啶酮衍生物；其盐；以及含有这些化合物的除草剂。更详细地说，提供了通式[I]所表示的2-吡啶酮衍生物或其农药可接受的盐，以及含有这些化合物的除草剂。在通式[I]中，X1是氧原子或硫原子；X2、X3和X4分别为CH或N(O)m；m是0或1的整数；R1是氢原子，C1-12烷基或类似物；R2是卤素原子，氰基或类似物；n是0到4的整数；R3是羟基，卤素原子或类似物；A1是C(R11R12)；A2是C(R13R14)或C═O；A3是C(R15R16)；R11、R12、R13、R14、R15和R16分别独立地是氢原子或C1-6烷基基团。
• Phosphine-Catalyzed [3+2] Cyclizations: Applications to the Enantioselective Synthesis of Cyclopentene-Fused Chromanones and Dihydroquinolinones
  作者：Angela Marinetti、Mathilde Neel、Jérôme Gouin、Arnaud Voituriez

  DOI：10.1055/s-0030-1260466

  日期：2011.6

  Phosphine-promoted [3+2] cyclizations of allenic esters or phosphonates with coumarin derivatives were used to synthesize functionalized bicyclo[4.3.0]chroman-2-ones. Analogous bicy­clo[4.3.0]quinolinones were similarly prepared by a two-step strategy involving a phosphine-catalyzed [3+2] cyclization of diethyl propadienylphosphonate and 3-(2-nitrophenyl)acrylate as the key step. Enantiomerically enriched compounds, with enantiomeric excesses in the range 70-86%, were obtained by using (S,S)-Ferro­PHANE as the chiral catalyst for the cyclization step.

  通过磷烯促进的[3+2]环化反应，将烯烃酯或膦酸酯与香豆素衍生物结合，合成了功能化的双环[4.3.0]色烯-2-酮。类似的双环[4.3.0]喹啉酮通过两步策略制备，其中关键步骤是磷烯催化的[3+2]环化反应，反应物为二乙基丙炔基膦酸酯和3-(2-硝基苯基)丙烯酸酯。通过使用(S,S)-铁磷烯作为环化步骤的手性催化剂，获得了光学纯度在70-86%范围内的富含对映体的化合物。
• Ring-fused 2-pyridone derivatives and herbicides
  申请人：Kumiai Chemical Industry Co., Ltd.

  公开号：US08334236B2

  公开（公告）日：2012-12-18

  Provided are 2-pyridone derivatives which have excellent herbicidal activity and exhibit high safety to useful crops and so on; salts thereof; and herbicides containing same. In more detail, 2-pyridone derivatives represented by general formula [I] or agrochemically acceptable salts thereof, and herbicides containing these compounds are provided. In general formula [I], X1 is an oxygen atom or a sulfur atom; X2, X3, and X4 are to each CH or N(O)m; m is an integer of 0 or 1; R1 is a hydrogen atom, a C1-12 alkyl group, or the like; R2 is a halogen atom, a cyano group, or the like; n is an integer of 0 to 4; R3 is a hydroxyl group, a halogen atom, or the like; A1 is C(R11R12); A2 is C(R13R14) or C═O; A3 is C(R15R16); and R11, R12, R13, R14, R15, and R16 are each independently a hydrogen atom or a C1-6 alkyl group.

  提供了具有出色除草活性并对有用作物等表现出高安全性的2-吡啶酮衍生物；其盐；以及含有它们的除草剂。更详细地说，提供了由通式[I]表示的2-吡啶酮衍生物或农药上可接受的盐，以及含有这些化合物的除草剂。在通式[I]中，X1是氧原子或硫原子；X2、X3和X4分别为CH或N(O)m；m是0或1的整数；R1是氢原子、C1-12烷基或类似物；R2是卤素原子、氰基或类似物；n是0到4的整数；R3是羟基、卤素原子或类似物；A1是C(R11R12)；A2是C(R13R14)或C═O；A3是C(R15R16)；R11、R12、R13、R14、R15和R16各自独立地是氢原子或C1-6烷基。
• The Discovery and Hit-to-Lead Optimization of Tricyclic Sulfonamides as Potent and Efficacious Potentiators of Glycine Receptors
  作者：Howard Bregman、Jeffrey R. Simard、Kristin L. Andrews、Shawn Ayube、Hao Chen、Hakan Gunaydin、Angel Guzman-Perez、Jiali Hu、Liyue Huang、Xin Huang、Paul H. Krolikowski、Sonya G. Lehto、Richard T. Lewis、Klaus Michelsen、Pamela Pegman、Matthew H. Plant、Paul L. Shaffer、Yohannes Teffera、Shuyan Yi、Maosheng Zhang、Jacinthe Gingras、Erin F. DiMauro

  DOI：10.1021/acs.jmedchem.6b01496

  日期：2017.2.9

  Current pain therapeutics suffer from undesirable psychotropic and sedative side effects, as well as abuse potential. Glycine receptors (GlyRs) are inhibitory ligand-gated ion channels expressed in nerves of the spinal dorsal horn, where their activation is believed to reduce transmission of painful stimuli. Herein, we describe the identification and hit-to-lead optimization of a novel class of tricyclic sulfonamides as allosteric GlyR potentiators. Initial optimization of high-throughput screening (HTS) hit 1 led to the identification of 3, which demonstrated ex vivo potentiation of glycine-activated current in mouse dorsal horn neurons from spinal cord slices. Further improvement of potency and pharmacokinetics produced in vivo proof-of-concept tool molecule 20 (AM-1488), which reversed tactile allodynia in a mouse spared-nerve injury (SNI) model. Additional structural optimization provided highly potent potentiator 32 (AM-3607), which was cocrystallized with human GlyR alpha 3(cryst) to afford the first described potentiator-bound X-ray cocrystal structure within this class of ligand-gated ion channels (LGICs).
• α-Diazo β-Keto Ester as Precursor to Aromatic CH Insertion and Wolff Rearrangement with Different Directing Groups
  作者：Biao Ma、Fang-Lei Chen、Xing-Yu Xu、Yi-Nan Zhang、Li-Hong Hu

  DOI：10.1002/adsc.201300763

  日期：2014.2.10

  AbstractA tunable aromatic CH insertion and a Wolff rearrangement of α‐diazo β‐keto esters precursor were developed. Different directing groups on nitrogen led with high selectivity to either dihydroquinoline or 2‐carbamoylacrylate motifs, which can be transformed to multiple heterocyclic scaffolds.magnified image