4,6-dimethyl-pyridine-2-carboxylic acid methyl ester | 69971-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,6-dimethyl-pyridine-2-carboxylic acid methyl ester
• 英文别名: 4,6-Dimethyl-pyridin-2-carbonsaeure-methylester；Methyl-4,6-dimethyl-2-pyridincarboxylat；Methyl 4,6-dimethylpicolinate；methyl 4,6-dimethylpyridine-2-carboxylate
• CAS: 69971-38-6
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: ZATJRKPUGUEWGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4,6-dimethyl-pyridine-2-carboxylic acid methyl ester 在 ammonium hydroxide 作用下， 生成 4,6-二甲基-2-吡啶甲酰胺
  参考文献：
  名称：

  关于杂环羧酸的一些衍生物II。金属离子和生物学效应，18.平均

  摘要：

  描述了6-苯基-，4，6-二甲基-和5-甲基-吡啶甲酸的酰胺，取代的酰胺和酰肼的合成。

  DOI：

  10.1002/hlca.19540370118
• 作为产物：
  描述：

  2,4,6-三甲基吡啶 在 air 、 vanadium(V)-oxide-molybdenum (VI)-oxide silica gel-catalyst 、 硫酸 、 水 、 双氧水 作用下， 生成 4,6-dimethyl-pyridine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Mathes; Sauermilch, Chemische Berichte, 1955, vol. 88, p. 1276,1281

  摘要：

  DOI：

文献信息

• Alcohols as alkylating agents in heteroarene C–H functionalization
  作者：Jian Jin、David W. C. MacMillan

  DOI：10.1038/nature14885

  日期：2015.9

  The biochemical process of spin-centre shift is used to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors; this represents the first broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. A central reaction in DNA biosynthesis is ribonucleotide deoxygenation via the radical-mediated elimination of H2O, which is an example of 'spin-centre shift' (SCS), during which an alcohol C–O bond is cleaved to produce in a carbon-centred radical intermediate. Although SCS is a well-understood biochemical process, it is underutilized by the synthetic organic chemistry community. Here Jian Jin and David MacMillan show that it is possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylations using alcohols as radical precursors. This method represents the first broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the merger of photoredox and hydrogen atom transfer catalysis. Redox processes and radical intermediates are found in many biochemical processes, including deoxyribonucleotide synthesis and oxidative DNA damage1. One of the core principles underlying DNA biosynthesis is the radical-mediated elimination of H2O to deoxygenate ribonucleotides, an example of ‘spin-centre shift’2, during which an alcohol C–O bond is cleaved, resulting in a carbon-centred radical intermediate. Although spin-centre shift is a well-understood biochemical process, it is underused by the synthetic organic chemistry community. We wondered whether it would be possible to take advantage of this naturally occurring process to accomplish mild, non-traditional alkylation reactions using alcohols as radical precursors. Because conventional radical-based alkylation methods require the use of stoichiometric oxidants, increased temperatures or peroxides3,4,5,6,7, a mild protocol using simple and abundant alkylating agents would have considerable use in the synthesis of diversely functionalized pharmacophores. Here we describe the development of a dual catalytic alkylation of heteroarenes, using alcohols as mild alkylating reagents. This method represents the first, to our knowledge, broadly applicable use of unactivated alcohols as latent alkylating reagents, achieved via the successful merger of photoredox and hydrogen atom transfer catalysis. The value of this multi-catalytic protocol has been demonstrated through the late-stage functionalization of the medicinal agents, fasudil and milrinone.

  利用自旋中心转移的生化过程，通过醇作为自由基前体，可以实现温和的、非传统的烷基化反应。这在合成有机化学领域尚未得到充分应用。本文中Jin Jian和David MacMillan展示了一种方法，即利用这一自然发生的自旋中心转移过程，以醇作为自由基前体，实现温和、非传统的烷基化反应。这种方法首次实现了在广泛应用上将非活化醇作为潜在烷基化试剂，其核心是通过光氧化还原与氢原子转移催化的结合来实现。氧化还原过程和自由基中间体在很多生化过程中都存在，包括脱氧核糖核酸的合成和氧化性DNA损伤。DNA生物合成的关键原理之一就是通过自由基介导的水分子消除反应来脱氧核糖核苷酸，这也是"自旋中心转移"的一个例子。在这个过程中，醇的C-O键断裂，形成碳中心的自由基中间产物。虽然自旋中心转移是一个广为人知的生化过程，但在合成有机化学领域，这一方法尚未得到广泛应用。我们想知道是否有可能利用这个自然发生的自旋中心转移过程，以醇作为自由基前体，实现温和、非传统的烷基化反应。传统的基于自由基的烷基化方法通常需要使用化学计量的氧化剂、提高温度或使用过氧化物，因此一个使用简单且丰富的烷基化试剂的温和协议在合成多样功能化的药物分子上具有很大的应用价值。在这里，我们描述了一种使用醇作为温和烷基化试剂的双催化烷基化杂芳烃的方法。据我们所知，这代表了首次在广泛应用上将非活化醇作为潜在烷基化试剂，其成功在于实现了光氧化还原与氢原子转移催化的结合。该多催化协议的价值已通过药物分子法舒地尔和米力农的后期功能化得到展示。
• TRI-SUBSTITUTED PYRIMIDINE COMPOUNDS AND THEIR USE AS PDE10 INHIBITORS
  申请人：Kawanishi Eiji

  公开号：US20110160206A1

  公开（公告）日：2011-06-30

  The present invention provides a tri-substituted pyrimidine compound having an excellent PDE10 inhibitory activity. The present invention relates to a tri-substituted pyrimidine compound represented by the following formula [I 0 ] or a pharmaceutically acceptable salt thereof, a method for preparing the same, and use of said compound for PDE10 inhibitor, and a pharmaceutical composition comprising said compounds as an active ingredient: wherein: either one of X 1 and X 2 is N, and the other of X 1 and X 2 is CH; A is *-CH═CH—, *-C(Alk)=CH—, *-CH 2 —CH 2 — or *-O—CH 2 — (* is a bond with R 1 ); Alk is a lower alkyl group; Ring B is an optionally substituted nitrogen-containing aliphatic heterocyclic group; R 1 is an optionally substituted quinoxalinyl or an optionally substituted quinolyl; Y 0 is mono- or di-substituted amino group, or a pharmaceutically acceptable salt thereof.

  本发明提供了一种具有优异的PDE10抑制活性的三取代嘧啶化合物。本发明涉及一种由以下式[I0]表示的三取代嘧啶化合物或其药学上可接受的盐，以及制备该化合物的方法，以及将所述化合物用作PDE10抑制剂的用途，以及包含所述化合物作为活性成分的药物组合物：其中：X1和X2中的任一者为N，另一者为CH；A为*-CH═CH—，*-C(Alk)=CH—，*-CH2—CH2—或*-O—CH2—（*是与R1形成键）；Alk为较低的烷基基团；环B为可选择地取代的含氮脂肪杂环基团；R1为可选择地取代的喹唑啉基或可选择地取代的喝啉基；Y0为单取代或双取代的氨基团，或其药学上可接受的盐。
• NAPHTHYRIDIN-2(1H) -ONE COMPOUNDS USEFUL AS ANTIBACTERIALS
  申请人：ALEMPARTE-GALLARDO Carlos

  公开号：US20110319424A1

  公开（公告）日：2011-12-29

  Compounds of Formula (I), wherein substituents R 1 , R 2 and R 5 are as defined, and Ar represents substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, furanyl, imidazolyl and thiophenyl; compositions containing them, their use in therapy, including their use as antibacterials, for example in the treatment of tuberculosis, and methods for the preparation of such compounds, are provided.

  本发明提供了化学式(I)的化合物，其中取代基R1、R2和R5如定义所述，Ar代表取代的苯基、吡啶基、吡嗪基、嘧啶基、吡咯嗪基、噻唑基、呋喃基、咪唑基和噻吩基；含有它们的组合物，它们在治疗中的使用，包括它们作为抗菌剂的使用，例如在结核病的治疗中，以及制备这种化合物的方法。
• Organic electroluminescent compound and organic electroluminescent device comprising the same
  申请人：Rohm and Haas Electronic Materials Korea Ltd.

  公开号：US10276808B2

  公开（公告）日：2019-04-30

  The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound according to the present disclosure is capable of producing an organic electroluminescent device with reasonably improved color purity and efficiency.

  本公开涉及一种有机电致发光化合物和包含该化合物的有机电致发光器件。根据本公开的有机电致发光化合物能够生产出具有合理改进的色纯度和效率的有机电致发光器件。
• [EN] NAPHTHYRIDIN-2(1H) -ONE COMPOUNDS USEFUL AS ANTIBACTERIALS<br/>[FR] COMPOSÉS DE NAPHTYRIDIN-2(1H)-ONE UTILES EN TANT QU'ANTIBACTÉRIENS
  申请人：GLAXO GROUP LTD

  公开号：WO2009090222A1

  公开（公告）日：2009-07-23

  Compounds of Formula (I), wherein substituents R1, R2 and R5 are as defined, and Ar represents substituted phenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl, furanyl, imidazolyl and thiophenyl; compositions containing them, their use in therapy, including their use as antibacterials, for example in the treatment of tuberculosis, and methods for the preparation of such compounds, are provided.