2-Methyl-6-pyridin-2-ylethynyl-pyridine | 824389-35-7

• 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: 2-Methyl-6-pyridin-2-ylethynyl-pyridine
• 英文别名: 2-Methyl-6-(2-(pyridin-2-yl)ethynyl)pyridine；2-methyl-6-(2-pyridin-2-ylethynyl)pyridine
• CAS: 824389-35-7
• 化学式: C₁₃H₁₀N₂
• 分子量: 194.236
• InChiKey: WVUMTMFBRIPBOS-UHFFFAOYSA-N

物化性质

• 沸点：
  360.5±32.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methyl-6-pyridin-2-ylethynyl-pyridine 在 1,1,2,2-四氟-1,2-二溴乙烷 、 cesium fluoride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.42h， 生成 2-Benzenesulfonylmethyl-6-pyridin-2-ylethynyl-pyridine
  参考文献：
  名称：

  Double elimination protocol for the synthesis of arylene ethynylenes containing heteroaromatic rings

  摘要：

  β-取代磺酮的双消除反应提供了一种多功能的合成芳基乙炔基套件的策略，其中包含杂芳环。 α-磺酰基碳负离子与醛之间的醛缩反应序列，捕获所得的醛缩物以给出β-取代磺酮，以及对该中间体的双消除可以集成在一个反应器中。该方案允许噻吩、吡啶和二茂铁单元被容纳在苯基乙炔基阵列中。关键词：芳基-乙炔基，杂芳环，二茂铁，双消除，磺酮。

  DOI：

  10.1139/v05-038
• 作为产物：
  描述：

  2-溴-6-甲基吡啶 在 双三苯基磷二氯化钯 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-Methyl-6-pyridin-2-ylethynyl-pyridine
  参考文献：
  名称：

  Synthesis and receptor assay of aromatic–ethynyl–aromatic derivatives with potent mGluR5 antagonist activity

  摘要：

  Noncompetitive antagonists of the human metabotropic glutamate receptor subtype 5 (mGluR5) have been implicated as potential therapeutics for the treatment of a variety of nervous system disorders, including pain, anxiety, and drug addiction. To discover novel noncompetitive antagonists to the mGluR5, we initiated an SAR study around the known lead compounds MPEP and M-MPEP. Our results pointed out the critical role of the para position of the two aromatic rings, which leads to inactive products and permitted the discovery of potent mGluR5 antagonists (e.g., 16, 25, 28, 34 IC50 = 13.5, 11.9, 21, 15nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.042

文献信息

• Synthesis and biological evaluation of fenobam analogs as mGlu5 receptor antagonists
  作者：Georg Jaeschke、Richard Porter、Bernd Büttelmann、Simona M. Ceccarelli、Wolfgang Guba、Bernd Kuhn、Sabine Kolczewski、Jörg Huwyler、Vincent Mutel、Jens-Uwe Peters、Theresa Ballard、Eric Prinssen、Eric Vieira、Jürgen Wichmann、Will Spooren

  DOI：10.1016/j.bmcl.2006.12.033

  日期：2007.3

  Optimization of affinity and microsomal stability led to identification of the potent, metabolically stable fenobam analog 4l. Robust in vivo efficacy of 4l was demonstrated in four different models of anxiety. Additionally, a ligand based pharmacophore alignment of fenobam and MPEP is proposed.

  亲和力和微粒体稳定性的优化导致了有效的，代谢稳定的非诺贝类似物4l的鉴定。在四种不同的焦虑模型中证明了4l具有强大的体内功效。另外，提出了基于配体的非诺贝特和MPEP的药效团比对。
• Synthesis and receptor assay of aromatic–ethynyl–aromatic derivatives with potent mGluR5 antagonist activity
  作者：David Alagille、Ronald M. Baldwin、Bryan L. Roth、Jarda T. Wroblewski、Ewa Grajkowska、Gilles D. Tamagnan

  DOI：10.1016/j.bmc.2004.09.042

  日期：2005.1

  Noncompetitive antagonists of the human metabotropic glutamate receptor subtype 5 (mGluR5) have been implicated as potential therapeutics for the treatment of a variety of nervous system disorders, including pain, anxiety, and drug addiction. To discover novel noncompetitive antagonists to the mGluR5, we initiated an SAR study around the known lead compounds MPEP and M-MPEP. Our results pointed out the critical role of the para position of the two aromatic rings, which leads to inactive products and permitted the discovery of potent mGluR5 antagonists (e.g., 16, 25, 28, 34 IC50 = 13.5, 11.9, 21, 15nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.
• Double elimination protocol for the synthesis of arylene ethynylenes containing heteroaromatic rings
  作者：Akihiro Orita、Fangguo Ye、Govindarajulu Babu、Tomohiro Ikemoto、Junzo Otera

  DOI：10.1139/v05-038

  日期：2005.6.1

  The double elimination reaction of β-substituted sulfones offers a versatile strategy for synthesis of arylene ethynylene kits containing heteroaromatic rings. A sequence of aldol reaction between α-sulfonyl carbanion and aldehyde, trapping the resulting aldolate to give β-substituted sulfone, and double elimination of this intermediate can be integrated in one pot. This protocol allows thiophene, pyridine, and ferrocene units to be accommodated in phenylene ethynylene arrays.Key words: arylene–ethynylenes, heteroaromatic rings, ferrocene, double elimination, sulfones.

  β-取代磺酮的双消除反应提供了一种多功能的合成芳基乙炔基套件的策略，其中包含杂芳环。 α-磺酰基碳负离子与醛之间的醛缩反应序列，捕获所得的醛缩物以给出β-取代磺酮，以及对该中间体的双消除可以集成在一个反应器中。该方案允许噻吩、吡啶和二茂铁单元被容纳在苯基乙炔基阵列中。关键词：芳基-乙炔基，杂芳环，二茂铁，双消除，磺酮。