CAS: 80673-00-3; 3-((Trimethylsilyl)Ethynyl)Pyridine

该化合物是一种多功能有机硅化合物,其特点是与三甲基硅保护苯乙烯组相连的环. 这种结构使它成为有机合成中有价值的中间体,特别是对于Sonogashira和Heck的相联反应(如Sonogashira和Heck的相联反应)而言尤其如此. 三甲基硅基组增强了稳定性和处理能力,而苯乙烯会允许进一步功能化.它的核心有助于协调化学,使离子体设计和金属-有机框架(MOFs)的应用成为可能.由于其反应性和模块性,该化合物在制药和材料科学研究中特别有用.建议在惰性条件下进行妥善处理,以保持其完整性.

结构式图片

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267244-88-2 250252-33-6 866683-29-6

物理性质

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上下游产品

3-Bromopyridine trimethylsilylacetylene 3-bromopyridine hydr°Chloride pyridine-3-carbonitrile 3-Ethynylpyridine (E/Z)-3-(2-methoxyvinyl)pyridine 3-(1,1-diphenylethyl)pyridine 1-benzenesulfonyl-5-methanesulfonyl-2-(pyridin-3-yl)indole

合成工艺路线路线简述

  • 合成目标产物 3-(Trimethylsilylethynyl)Pyridine 主要起始原料 3-Ethynylpyridine And Chlorotrimethylsilane
  • 467220-34-4 + 626-55-1 = 80673-00-3
    反应条件:1.1 Catalysts: Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran1.2 Reagents: Hydrochloric Acid Solvents: Water
    标题:Palladium-Catalyzed Cross-Alkynylation Of Aryl Bromides By Sodium Tetraalkynylaluminates
    作者:Gelman,Dmitri; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2002 卷标:67(18) 页码:6287-6290]

    1066-54-2 + 1120-90-7 = 80673-00-3
    反应条件:1.1 Catalysts: Cuprous Iodide,Dichlorobis(Triphenylphosphine)Palladium Solvents: Triethylamine; 3 H,Rt; 1 H,Rt
    标题:Palladium-Catalyzed Trifluoroethylation Of Terminal Alkynes With 1,1,1-Trifluoro-2-Iodoethane
    作者:Feng,Yi-Si; Et Al
    参考文献:Organic Letters 日期:2013 卷标:15(4) 页码:936-939]

    2510-23-8 + 14630-40-1 = 80673-00-3
    反应条件:1.1 Catalysts: Potassium Bis(Trimethylsilyl)Amide Solvents: Acetonitrile; 2 H,Rt
    标题:Transition Metal-Free Catalytic C-H Silylation Of Terminal Alkynes With Bis(Trimethylsilyl)Acetylene Initiated By Khmds
    作者:Kucinski,Krzysztof; Et Al
    参考文献:Chemcatchem 日期:2022 卷标:14(18)]

    2510-23-8 + 75-77-4 = 80673-00-3
    反应条件:1.1 Reagents: Diethylzinc Solvents: Acetonitrile,Hexane; 20 H,80 °C
    标题:Et2Zn-Mediated Stoichiometric C(Sp)-H Silylation Of 1-Alkynes And Chlorosilanes
    作者:Huang,Pan; Et Al
    参考文献:Tetrahedron Letters 日期:2019 卷标:60(24) 页码:1574-1577]

    1066-54-2 + 626-55-1 = 80673-00-3
    反应条件:1.1 Reagents: Diisopropylamine Catalysts: Cuprous Iodide,Dichlorobis(Triphenylphosphine)Palladium; 3 H,30 °C1.2 Reagents: Water
    标题:Efficient Synthesis Of A Complete Donor/acceptor Bis(Aryl)Diyne Family
    作者:Holmes,Brian T.; Et Al
    参考文献:Synthetic Communications 日期:2003 卷标:33(14) 页码:2447-2461]

    1066-54-2 + 626-55-1 = 80673-00-3
    反应条件:1.1 Reagents: Triethylamine Catalysts: Cuprous Iodide,Dichlorobis(Triphenylphosphine)Palladium; 5 H,50 °C
    标题:Octahedral [pd6L8]12+ Metallosupramolecular Cages: Synthesis,Structures And Guest-Encapsulation Studies
    作者:Kim,Tae Y.; Et Al
    参考文献:Chemistry - A European Journal 日期:2017 卷标:23(60) 页码:15089-15097]

    2510-23-8 + 81290-20-2 = 80673-00-3
    反应条件:1.1 Solvents: 1,3-Dimethyl-3,4,5,6-Tetrahydro-2(1H)-Pyrimidinone; 24 H,40 °C1.2 Reagents: Ammonium Chloride Solvents: Water
    标题:Highly Chemoselective Dmpu-Mediated Trialkylsilylation Of Terminal Alkynes Using Trifluoromethyltrialkylsilane
    作者:Nozawa-Kumada,Kanako; Et Al
    参考文献:Asian Journal Of Organic Chemistry 日期:2017 卷标:6(1) 页码:63-66]

    1066-54-2 + 1120-90-7 = 80673-00-3
    反应条件:1.1 Reagents: Triethylamine Catalysts: Cuprous Iodide,Dichlorobis(Triphenylphosphine)Palladium Solvents: Acetonitrile; 4 H,Rt
    标题:Novel Class Of Colony-Stimulating Factor 1 Receptor Kinase Inhibitors Based On An O-Aminopyridyl Alkynyl Scaffold As Potential Treatment For Inflammatory Disorders
    作者:Xie,Zhicheng; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2020 卷标:63(3) 页码:1397-1414]

    1066-54-2 + 1120-90-7 = 80673-00-3
    反应条件:1.1 Reagents: Triethylamine Catalysts: Cuprous Iodide,Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 12 H,40 °C
    标题:Substituent Parameters Impacting Isomer Composition And Optical Properties Of Dihydroindolizine Molecular Switches
    作者:Bartucci,Matthew A.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2014 卷标:79(12) 页码:5586-5594]

    2510-23-8 + 75-77-4 = 80673-00-3
    反应条件:1.1 Reagents: Lithium Bis(Trimethylsilyl)Amide Solvents: Tetrahydrofuran; 2 Min,-78 °C; 1 H,-78 °C1.2 -78 °C; -78 °C -> Rt; 17.5 H,Rt1.3 Reagents: Water; Rt
    标题:Improved Syntheses Of The Mglu5 Antagonists Mmpep And Mtep Using Sonogashira Cross-Coupling
    作者:Mu,Boshuai; Et Al
    参考文献:Pharmaceuticals 日期:2018 卷标:11(1) 页码:24/1-24/13]

    6224-91-5 + 223562-51-4 = 80673-00-3
    反应条件:1.1 Catalysts: (T-4)-[(4-Methoxyphenyl)Methylidyne]Tris(1,1,1-Triphenylsilanolato)Molybdenum Solvents: Toluene; 2 H,Rt
    标题:Cross-Metathesis Of Terminal Alkynes
    作者:Lhermet,Rudy; Et Al
    参考文献:Chemistry - A European Journal 日期:2014 卷标:20(41) 页码:13188-13193]

    1066-54-2 + 100-54-9 = 80673-00-3
    反应条件:1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran,Hexane; 0 °C; 0 °C -> Rt; 15 Min,Rt; Rt -> 0 °C1.2 Reagents: Zinc Bromide Solvents: Tetrahydrofuran; 0 °C -> Rt; 30 Min,Rt1.3 Reagents: Tridecane Catalysts: Dichlorobis(Trimethylphosphine)Nickel Solvents: Tetrahydrofuran; 20 H,65 °C1.4 Reagents: Citric Acid,Sodium Salt Solvents: Tert-Butyl Methyl Ether,Water
    标题:Alkynylation Of Benzonitriles Via Nickel Catalyzed C-C Bond Activation
    作者:Penney,Jonathan M.; Et Al
    参考文献:Tetrahedron Letters 日期:2004 卷标:45(25) 页码:4989-4992]

    3468-53-9 + 1066-54-2 = 80673-00-3
    反应条件:1.1 Reagents: Diethylamine Catalysts: Cuprous Iodide,Palladium Acetylacetonate,1,1′-(3,4-Thiophenediyl)Bis[1,1-Dicyclohexylphosphine] Solvents: 1,4-Dioxane; 16 H,150 °C
    标题:Palladium-Catalyzed Decarbonylative Alkynylation Of Aromatic Esters
    作者:Okita,Toshimasa; Et Al
    参考文献:Chemistry Letters 日期:2017 卷标:46(2) 页码:218-220]

    2510-23-8 + 27607-77-8 = 80673-00-3
    反应条件:1.1 Reagents: Triethylamine Catalysts: Zinc Triflate Solvents: Dichloromethane; Overnight,Rt1.2 Reagents: Ammonium Chloride Solvents: Water; Rt
    标题:Ligand-Promoted Alkynylation Of Aryl Ketones: A Practical Tool For Structural Diversity In Drugs And Natural Products
    作者:Xu,Hui; Et Al
    参考文献:Acs Catalysis 日期:2021 卷标:11(3) 页码:1758-1764]

    626-55-1 = 80673-00-3 [标题:Reaction Conditions
    标题:Inhibitors To Overcome Secondary Mutations In The Stem Cell Factor Receptor Kit
    作者:Kaitsiotou,Helena; Et Al
    参考文献:Journal Of Medicinal Chemistry 日期:2017 卷标:60(21) 页码:8801-8815]

    59-67-6 = 80673-00-3
    反应条件:1.1 Reagents: 1-Ethyl-3-(3′-Dimethylaminopropyl)Carbodiimide Hydrochloride Catalysts: 4-(Dimethylamino)Pyridine Solvents: Dichloromethane; > 1 H,Rt1.2 Reagents: Sodium Bicarbonate Solvents: Water2.1 Reagents: Diethylamine Catalysts: Cuprous Iodide,Palladium Acetylacetonate,1,1′-(3,4-Thiophenediyl)Bis[1,1-Dicyclohexylphosphine] Solvents: 1,4-Dioxane; 16 H,150 °C
    标题:Palladium-Catalyzed Decarbonylative Alkynylation Of Aromatic Esters
    作者:Okita,Toshimasa; Et Al
    参考文献:Chemistry Letters 日期:2017 卷标:46(2) 页码:218-220]

    462-08-8 = 80673-00-3
    反应条件:1.1 Reagents: P-Toluenesulfonic Acid,Sodium Nitrite,Potassium Iodide Solvents: Acetonitrile; Rt -> 10 °C; 10 Min,10 °C; 1 H,10 °C -> Rt1.2 Reagents: Sodium Bicarbonate Solvents: Water; Ph 9 - 10,Rt2.1 Reagents: Triethylamine Catalysts: Cuprous Iodide,Dichlorobis(Triphenylphosphine)Palladium Solvents: Tetrahydrofuran; 12 H,40 °C
    标题:Substituent Parameters Impacting Isomer Composition And Optical Properties Of Dihydroindolizine Molecular Switches
    作者:Bartucci,Matthew A.; Et Al
    参考文献:Journal Of Organic Chemistry 日期:2014 卷标:79(12) 页码:5586-5594
📜3-氨基吡啶置于copper(L) Iodide,Trans-Bis(Triphenylphosphine)Palladium Dichloride,对甲苯磺酸,三乙胺,Potassium Iodide,Sodium Nitrite体系中,用 四氢呋喃,水,乙酸乙酯 作为反应溶剂,化学反应 13.17H,反应生成 3-(三甲硅乙炔基)吡啶
参考文献:影响二氢吲哚嗪分子开关的异构体组成和光学性质的取代基参数
标题:影响二氢吲哚嗪分子开关的异构体组成和光学性质的取代基参数
摘要:为了了解哪些因素影响6'-和8'-取代的二氢吲哚并嗪(dhi)的结构异构体控制,将一系列不对称吡啶与二甲基螺[cycloprop [2] Ene-1,9'-芴]-缩合. 2,3-二羧酸盐.吡啶衍生物上的取代基从供体到退出范围不等,并且证明了对所有dhi的异构体比率的控制.事实证明,取代基的控制对高度捐赠的氨基具有选择性,后者专门形成了8'异构体.通过光解实验可以得到相同的比例,这表明缩合反应主要由产物的热力学稳定性决定.取代基的电子影响超出了异构体的控制范围,因为它影响dhi的光学性能和电化(转换)速率,形成螺旋构象异构体.
DOI:10.1021/jo500752P

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主要参考文献

参考标题:Novel 3-Phenylprop-2-Ynylamines As Inhibitors Of Mammalian Squalene Epoxidaseelectronic Supplementary Information (Esi) Available: Proton Nmr Spectra For The Intermediate Piperidines 56-60 And Acetylenes 63-81 And 85,86. See Http://www.Rsc.Org/suppdata/ob/b2/b209165H/
作者:David L. Musso,Morris J. Clarke,James L. Kelley,G. Evan Boswell,Grace Chen |发布日期:2003.1.30
摘要:The Synthesis Of A Novel Series Of 3-Phenylprop-2-Ynylamines As Selective Mammalian Squalene Epoxidase Inhibitors Is Described. Structure-Activity Relationship Studies Led To The Discovery Of Compound 19, 1-[3-(3,5-Dichlorophenyl)Prop-2-Ynyl]-3-Methylpiperidine Hydrochloride With An Ic50 Of 2.8 +/- 0.6 µm Against Rat Liver Squalene Epoxidase. Against 23 Strains Of Fungal Squalene Epoxidase Compound 19 Was Found To Be Inactive.

合成参考文献


摘要:Mérour, J.-Y.; Joseph, B., Science of Synthesis Knowledge Updates, (2016) 3, 40.
摘要:Chartoire, A.; Nolan, S. P., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2012) 1, 514.
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