3-(4-bromophenoxy)-2-methylpyridine | 1362703-22-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-bromophenoxy)-2-methylpyridine
• CAS: 1362703-22-7
• 化学式: C₁₂H₁₀BrNO
• 分子量: 264.121
• InChiKey: PHXFTVHPVZLGMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenoxy)-2-methylpyridine 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四(三苯基膦)钯 、 potassium acetate 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.34h， 生成 1-cyclopropylmethyl-4-[4-(2-methylpyridin-3-yloxy)-phenyl]-2-oxo-1,2-dihydropyridine-3-carbonitrile
  参考文献：
  名称：

  Discovery of 1,4-Disubstituted 3-Cyano-2-pyridones: A New Class of Positive Allosteric Modulators of the Metabotropic Glutamate 2 Receptor

  摘要：

  The discovery and characterization of compound 48, a selective and in vivo active mGlu2 receptor positive allosteric modulator (PAM), are described. A key to the discovery was the rational exploration of the initial HTS hit 13 guided by an overlay model built with reported mGlu2 receptor PAM chemotypes. The initial weak in vitro activity of the hit 13 was quickly improved, although compounds still had suboptimal druglike properties. Subsequent modulation of the physicochemical properties resulted in compounds having a more balanced profile, combining good potency and in vivo pharmacokinetic properties. Final refinement by addressing cardiovascular safety liabilities led to the discovery of compound 48. Besides good potency, selectivity, and ADME properties, compound 48 displayed robust in vivo activity in a sleep-wake electroencephalogram (sw-EEG) assay consistent with mGlu2 receptor activation, in accordance with previous work from our laboratories.

  DOI：

  10.1021/jm2016864
• 作为产物：
  描述：

  3-羟基-2-甲基吡啶 在 palladium 10% on activated carbon 、 氢溴酸 、 氢气 、 caesium carbonate 、 sodium nitrite 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 3-(4-bromophenoxy)-2-methylpyridine
  参考文献：
  名称：

  Discovery of 1,4-Disubstituted 3-Cyano-2-pyridones: A New Class of Positive Allosteric Modulators of the Metabotropic Glutamate 2 Receptor

  摘要：

  The discovery and characterization of compound 48, a selective and in vivo active mGlu2 receptor positive allosteric modulator (PAM), are described. A key to the discovery was the rational exploration of the initial HTS hit 13 guided by an overlay model built with reported mGlu2 receptor PAM chemotypes. The initial weak in vitro activity of the hit 13 was quickly improved, although compounds still had suboptimal druglike properties. Subsequent modulation of the physicochemical properties resulted in compounds having a more balanced profile, combining good potency and in vivo pharmacokinetic properties. Final refinement by addressing cardiovascular safety liabilities led to the discovery of compound 48. Besides good potency, selectivity, and ADME properties, compound 48 displayed robust in vivo activity in a sleep-wake electroencephalogram (sw-EEG) assay consistent with mGlu2 receptor activation, in accordance with previous work from our laboratories.

  DOI：

  10.1021/jm2016864

文献信息

• Heterocyclic insecticides
  申请人：ICI AMERICAS INC.

  公开号：EP0317259A2

  公开（公告）日：1989-05-24

  Insecticides of the general formula wherein R₁ is an optionally substituted 5- to 10-member heterocyclic moiety; R₂ is an optionally substituted alkyl, cycloalkyl or alkenyl moiety; X is oxygen, sulfur or -NH-; and R₃ is: (a) an optionally sub­stituted 3-phenoxyphenalkyl, 3-phenoxypyridylalkyl, 3-(pyridyloxy)phen­alkyl, 3-phenylaminophenalkyl, 3-benzylphenalkyl or 3-benzyloxyphenalkyl moiety; (b) a benzylfuranylmethyl moiety; (c) a 3- or 4-substituted benzyl or tetrafluorobenzyl moiety; (d) 4-phenoxy-2-butyn-2-yl; or (e) 2-methyl-­3-phenylbenzyl.

  通式如下的杀虫剂 其中 R₁ 是任选取代的 5 至 10 个杂环分子； R₂ 是任选取代的烷基、环烷基或烯基； X 是氧、硫或-NH-；以及 R₃ 是：(a) 任选取代的 3-苯氧基苯烷基、3-苯氧基吡啶烷基、3-（吡啶氧基）苯烷基、3-苯氨基苯烷基、3-苄基苯烷基或 3-苄氧基苯烷基；(b) 苄基呋喃甲基； (c) 3-或 4-取代苄基或四氟苄基； (d) 4-苯氧基-2-丁炔-2-基；或 (e) 2-甲基-3-苯基苄基。
• [EN] PYRIDAZINONES AND METHODS OF USE THEREOF<br/>[FR] PYRIDAZINONES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：GOLDFINCH BIO INC

  公开号：WO2019055966A3

  公开（公告）日：2019-04-18
• PYRIDAZINONES AND METHODS OF USE THEREOF
  申请人：Goldfinch Bio, Inc.

  公开号：EP3684364A2

  公开（公告）日：2020-07-29
• US4994473A
  申请人：——

  公开号：US4994473A

  公开（公告）日：1991-02-19
• US5064846A
  申请人：——

  公开号：US5064846A

  公开（公告）日：1991-11-12