2-((2-trimethylsilyl)acetylenyl)-5-cyanopyridine | 1214278-89-3

• 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-((2-trimethylsilyl)acetylenyl)-5-cyanopyridine
• 英文别名: 6-[(trimethylsilyl)ethynyl] pyridine-3-carbonitrile；6-((Trimethylsilyl)ethynyl)nicotinonitrile；6-(2-trimethylsilylethynyl)pyridine-3-carbonitrile
• CAS: 1214278-89-3
• 化学式: C₁₁H₁₂N₂Si
• 分子量: 200.315
• InChiKey: GGKISZDHOCHRKK-UHFFFAOYSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  275.5±40.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((2-trimethylsilyl)acetylenyl)-5-cyanopyridine 在 亚硝酸特丁酯 、 potassium carbonate 、 N-甲基苄胺 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 15.0h， 生成 2,5-二氰基吡啶
  参考文献：
  名称：

  芳基乙炔碳-碳三键断裂合成芳基腈无需金属催化剂

  摘要：

  实现了炔烃的碳-碳三键的裂解，从而在无过渡金属的条件下合成芳腈。大量的末端炔底物经历了这种反应，以中等至良好的产率提供相应的腈，并具有良好的官能团耐受性。

  DOI：

  10.1002/ejoc.201600438
• 作为产物：
  描述：

  2-溴-5-氰基吡啶 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 12.0h， 生成 2-((2-trimethylsilyl)acetylenyl)-5-cyanopyridine
  参考文献：
  名称：

  芳基乙炔碳-碳三键断裂合成芳基腈无需金属催化剂

  摘要：

  实现了炔烃的碳-碳三键的裂解，从而在无过渡金属的条件下合成芳腈。大量的末端炔底物经历了这种反应，以中等至良好的产率提供相应的腈，并具有良好的官能团耐受性。

  DOI：

  10.1002/ejoc.201600438

文献信息

• FLUORO-[1,3]OXAZINES AS BACE1 INHIBITORS
  申请人：WOLTERING Thomas

  公开号：US20150376172A1

  公开（公告）日：2015-12-31

  The present invention provides a compound of formula I having BACE1 inhibitory activity, their manufacture, pharmaceutical compositions containing them and their use as therapeutically active substances. The active compounds of the present invention are useful in the therapeutic and/or prophylactic treatment of e.g. Alzheimer's disease.

  本发明提供一种具有BACE1抑制活性的I型化合物，其制造方法，包含它们的制药组合物以及它们作为治疗活性物质的用途。本发明的活性化合物在治疗和/或预防阿尔茨海默病等疾病方面非常有用。
• A novel series of metabotropic glutamate receptor 5 negative allosteric modulators based on a 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine core
  作者：Guillaume Duvey、Benjamin Perry、Emmanuel Le Poul、Sonia Poli、Beatrice Bonnet、Nathalie Lambeng、Delphine Charvin、Tansy Donovan-Rodrigues、Hasnaà Haddouk、Stefania Gagliardi、Jean-Philippe Rocher

  DOI：10.1016/j.bmcl.2013.06.044

  日期：2013.8

  A series of potent non-acetylinic negative allosteric modulators of the metabotropic glutamate receptor 5 (mGlu5 NAMs) was developed starting from HTS screening hit 1. Potency was improved via iterative SAR, and physicochemical properties were optimized to deliver orally bioavailable compounds acceptable for in vivo testing. A lead molecule from the series demonstrated dose-dependent activity in the second phase of the rat formalin test from 30 mg/kg, and a preliminary PK/PD relationship was established. (c) 2013 Elsevier Ltd. All rights reserved.
• Synthesis, DNA binding, fluorescence measurements and antiparasitic activity of DAPI related diamidines
  作者：Abdelbasset A. Farahat、Arvind Kumar、Martial Say、Alaa El-Din M. Barghash、Fatma E. Goda、Hassan M. Eisa、Tanja Wenzler、Reto Brun、Yang Liu、Leah Mickelson、W. David Wilson、David W. Boykin

  DOI：10.1016/j.bmc.2009.12.011

  日期：2010.1

  A novel series of extended DAPI analogues were prepared by insertion of either a carbon-carbon triple bond (16a-d) or a phenyl group (21a, b and 24) at position-2. The new amidines were evaluated in vitro against both Trypanosoma brucei rhodesiense (T. b. r.) and Plasmodium falciparum (P. f.). Five compounds (16a, 16b, 16d, 21a, 21b) exhibited IC50 values against T. b. r. of 9 nM or less which is two to nine folds more effective than DAPI. The same five compounds exhibited IC50 values against P. f. of 5.9 nM or less which is comparable to that of DAPI. The fluorescence properties of these new molecules were recorded, however; they do not offer any advantage over those of DAPI. (C) 2009 Elsevier Ltd. All rights reserved.
• Cleavage of the Carbon-Carbon Triple Bonds of Arylacetylenes for the Synthesis of Arylnitriles without a Metal Catalyst
  作者：Yuanguang Lin、Qiuling Song

  DOI：10.1002/ejoc.201600438

  日期：2016.6

  Cleavage of the carbon–carbon triple bonds of alkynes was achieved, which led to the synthesis of arylnitriles under transition-metal-free conditions. A vast range of terminal alkyne substrates underwent this reaction to provide the corresponding nitriles in moderate to good yields with good functional group tolerance.

  实现了炔烃的碳-碳三键的裂解，从而在无过渡金属的条件下合成芳腈。大量的末端炔底物经历了这种反应，以中等至良好的产率提供相应的腈，并具有良好的官能团耐受性。
• Ru ^II and Ir ^III Complexes Containing ADA and DAD Triple Hydrogen Bonding Motifs: Potential Tectons for the Assembly of Functional Materials
  作者：Aidan P. McKay、Joseph I. Mapley、Keith C. Gordon、David A. McMorran

  DOI：10.1002/asia.201801748

  日期：2019.4.15

  characterisation of a series of [RuII(bpy)2L] and [Ir(ppy)2L] complexes containing ligands L with the potential to engage in triple hydrogen bonding interactions is described. L1 and L2 comprise pyridyl triazole chelating units with pendant diaminotriazine units, capable of donor‐acceptor‐donor (DAD) hydrogen bonding, while L3 and L4 contain ADA hydrogen bonding units proximal to N^N and N^O cleating sites, respectively

  描述了一系列含有配体L的[Ru II（bpy）2 L]和[Ir（ppy）2 L]配合物的合成和表征，该配合物具有参与三氢键合作用的潜力。L1和L2包含带有二氨基三嗪侧链的吡啶基三唑螯合单元，能够进行供体-受体-供体（DAD）氢键，而L3和L4分别包含靠近N ^ N和N ^ O裂解位点的ADA氢键单元。X射线晶体学分析显示含有Ru II配合物的L1和L2可通过氢键二聚体，而[Ru II（bpy）2 L 4 ]通过扩展的氢键基序组装形成一维链。相比之下，对于L3的Ru II和Ir III配合物，未观察到预期的氢键模式。光谱研究表明，配合物的吸收光谱是由MLCT和LLCT跃迁的组合产生的。Ir III和Ru II配合物的L1和L2配合物在固态发光，似乎氢键合到互补物质上可能会促进其3的调谐ILCT排放。低频拉曼光谱为L4配合物在固态中有序相互作用提供了进一步的证据，这与X射线晶体学的结果一致。