CAS: 78839-75-5; Tert-Butyl (2-Bromophenyl)Carbamate

该化合物是一种受保护的活性衍生物,其成分是圆形位置上的溴替代物和氮的三丁基碳基(Boc)组,该复合物是有机合成的多用途中间体,特别是在制药和农用化学应用方面.Boc组在反应过程中提供稳定性和选择性,使得在温酸条件下能够有控制地进行保护.Bromine money允许通过交叉反应,如Suzuki或Buchwald-Hartwig交错,进一步发挥作用.其晶体固态形式可以确保易于处理和储存.这些特性的结合使得N-Boc 2-Bromaniline是建造复杂的含氮的外环和精细化学物的宝贵建筑.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

ECHA物质C&L通报

上下游产品

tert-butyl dicarbonatedi-tert-butyl dicarbonate 2-bromoaniline 2-bromo-benzoyl azide tert-butyl alcoholtert-butyl alcoholtert-butyl phenylcarbamate (4aS,9aR)-4a-Hydroxy-1,2,3,4,4a,9a-hexahydro-carbazole-9-carboxylic acid tert-butyl ester N-allyl-N-(t-butoxycarbonyl)-2-bromoaniline 2-((trimethylsilyl)ethynyl)phenylamin°Carboxylic acid tert-butyl ester

合成工艺路线路线简述

  • 合成目标产物 N-(Tert-Butoxycarbonyl)-2-Bromoaniline 主要起始原料 Tert-Butyl N-Hydroxycarbamate
  • 24424-99-5 = 78839-75-5
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran
    标题:Pyrrole,Imidazolone And Imidazolidinone Chemistry For The Synthesis Of Heterocyclic Natural Products
    作者:Cantos-Llopart,Carme
    参考文献:2003]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Solvents: Tetrahydrofuran; 24 H,Reflux
    标题:Rhodium-Catalyzed Tandem Conjugate Addition-Mannich Cyclization Reaction: Straightforward Access To Fully Substituted Tetrahydroquinolines
    作者:Youn,So Won; Song,Ju-Hyun; Jung,Dai-Il
    参考文献:Journal Of Organic Chemistry 日期:2008 卷标:73(14) 页码:5658-5661]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; Reflux
    标题:Inhibition Studies With Rationally Designed Inhibitors Of The Human Low Molecular Weight Protein Tyrosine Phosphatase
    作者:Zabell,Adam P. R.; Corden,Steven; Helquist,Paul; Stauffacher,Cynthia V.; Wiest,Olaf
    参考文献:Bioorganic & Medicinal Chemistry 日期:2004 卷标:12(8) 页码:1867-1880]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Catalysts: Iron Oxide (Fe2O3) Solvents: Water; 70 Min,30 - 35 °C
    标题:Nano-γ-Fe2O3: Efficient,Reusable And Green Catalyst For N-Tert-Butoxycarbonylation Of Amines In Water
    作者:Medisetti,Venkataramana; Parimi,Umadevi; Anagani,Ramesh Babu; Satyanarayana,K. V. V. V.
    参考文献:Green And Sustainable Chemistry 日期:2014 卷标:4(2) 页码:95-101]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; 6 H,Reflux1.2 Reagents: Water
    标题:A Sequential Transition Metal And Organocatalytic Approach To The Enantioselective Synthesis Of C2-Spiroindoline Systems
    作者:Sah,Pooja; Gond,Aakash Kumar; Saini,Gaurav; Kapur,Manmohan
    参考文献:Organic Letters 日期:2023 卷标:25(51) 页码:9170-9175]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Solvents: Dichloromethane; 30 Min,0 °C1.2 Catalysts: 4-(Dimethylamino)Pyridine; 0 °C1.3 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane; 0 °C
    标题:Arene Dearomatization Via Radical Hydroarylation
    作者:Flynn,Autumn R.; Mcdaniel,Kelly A.; Hughes,Meredith E.; Vogt,David B.; Jui,Nathan T.
    参考文献:Chemrxiv 日期:2019 卷标:1 页码:1-9]

    3422-01-3 = 78839-75-5
    反应条件:1.1 Reagents: Tert-Butyllithium Solvents: Pentane,Tetrahydrofuran; -75 °C; 3 H,-50 °C; -75 °C1.2 Reagents: Carbon Tetrabromide Solvents: Tetrahydrofuran; -75 °C; > 1 Min,-75 °C
    标题:Nucleus- And Side-Chain Fluorinated 3-Substituted Indoles By A Suitable Combination Of Organometallic And Radical Chemistry
    作者:Bellezza,Francesca; Cipiciani,Antonio; Ruzziconi,Renzo; Spizzichino,Sara
    参考文献:Journal Of Fluorine Chemistry 日期:2008 卷标:129(2) 页码:97-107]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 1 H,Reflux; Reflux -> Rt; 30 Min,0 °C; Overnight,Reflux; Reflux -> Rt
    标题:Axial Chirality Control During Suzuki-Miyaura Cross-Coupling Reactions: The Tert-Butylsulfinyl Group As An Efficient Chiral Auxiliary
    作者:Colobert,Francoise; Valdivia,Victoria; Choppin,Sabine; Leroux,Frederic R.; Fernandez,Inmaculada; Et Al
    参考文献:Organic Letters 日期:2009 卷标:11(22) 页码:5130-5133]

    = 78839-75-5
    反应条件:1.1 Reagents: Cesium Carbonate Solvents: Acetonitrile; 1 H,100 °C1.2 Reagents: Ethyl Acetate
    标题:Base-Mediated Intramolecular Decarboxylative Synthesis Of Alkylamines From Alkanoyloxycarbamates
    作者:Li,Peihe; Ma,Nuannuan; Wang,Zheng; Dai,Qipu; Hu,Changwen
    参考文献:Journal Of Organic Chemistry 日期:2018 卷标:83(15) 页码:8233-8240]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Solvents: Tetrahydrofuran; 3 D,Reflux
    标题:Aryl Radical Cyclization With Alkyne Followed By Tandem Carboxylation In Methyl 4-Tert-Butylbenzoate-Mediated Electrochemical Reduction Of 2-(2-Propynyloxy)Bromobenzenes In The Presence Of Carbon Dioxide
    作者:Katayama,Asahi; Senboku,Hisanori; Hara,Shoji
    参考文献:Tetrahedron 日期:2016 卷标:72(31) 页码:4626-4636]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Catalysts: Sulfamic Acid; 15 Min,Rt
    标题:Efficient,Solventless N-Boc Protection Of Amines Carried Out At Room Temperature Using Sulfamic Acid As Recyclable Catalyst
    作者:Upadhyaya,Dharita J.; Barge,Alessandro; Stefania,Rachele; Cravotto,Giancarlo
    参考文献:Tetrahedron Letters 日期:2007 卷标:48(47) 页码:8318-8322]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; 6 H,Reflux; Cooled1.2 Reagents: Water
    标题:A Sequential Transition Metal And Organocatalytic Approach To The Enantioselective Synthesis Of C2-Spiroindoline Systems
    作者:Sah,Pooja; Gond,Aakash Kumar; Saini,Gaurav; Kapur,Manmohan
    参考文献:Chemrxiv 日期:2023 卷标:1 页码:1-11]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Reagents: Sodium Carbonate Solvents: 1,4-Dioxane,Water; 6 H,80 °C; 80 °C -> Rt1.2 Reagents: Water; Rt
    标题:Domino Pd0-Catalyzed C(Sp3)-H Arylation/electrocyclic Reactions Via Benzazetidine Intermediates
    作者:Rocaboy,Ronan; Dailler,David; Zellweger,Florian; Neuburger,Markus; Salome,Christophe; Et Al
    参考文献:Angewandte Chemie 日期:2018 卷标:57(37) 页码:12131-12135]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Catalysts: 4-(Dimethylamino)Pyridine Solvents: Tetrahydrofuran; 16 H,Reflux; Cooled1.2 Reagents: Potassium Carbonate Solvents: Methanol; 3 H,Reflux
    标题:Probing Cytochrome P450 (Cyp) Bioactivation With Chloromethylindoline Bioprecursors Derived From The Duocarmycin Family Of Compounds
    作者:Ortuzar,Natalia; Karu,Kersti; Presa,Daniela; Morais,Goreti R.; Sheldrake,Helen M.; Et Al
    参考文献:Bioorganic & Medicinal Chemistry 日期:2021 卷标:40]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Catalysts: 4-(Dimethylamino)Pyridine Solvents: Tetrahydrofuran; 24 H,Reflux
    标题:Indole Synthesis By Controlled Carbolithiation Of O-Aminostyrenes
    作者:Kessler,Albane; Coleman,Claire M.; Charoenying,Patchanee; O'Shea,Donal F.
    参考文献:Journal Of Organic Chemistry 日期:2004 卷标:69(23) 页码:7836-7846]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Solvents: Dichloromethane; 30 Min,0 °C1.2 Catalysts: 4-(Dimethylamino)Pyridine; 0 °C; 0 °C1.3 Solvents: Water1.4 Reagents: Trifluoroacetic Acid Solvents: Dichloromethane; 0 °C1.5 Solvents: Water; Basified
    标题:Hydroarylation Of Arenes Via Reductive Radical-Polar Crossover
    作者:Flynn,Autumn R.; Mcdaniel,Kelly A.; Hughes,Meredith E.; Vogt,David B.; Jui,Nathan T.
    参考文献:Journal Of The American Chemical Society 日期:2020 卷标:142(20) 页码:9163-9168]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Reagents: Sodium Hydride Solvents: Tetrahydrofuran; 1 H,Rt -> Reflux; Reflux -> Rt1.2 0.5 H,Rt1.3 Reagents: Sodium Hydride; 14 H,Rt -> Reflux; Reflux -> Rt1.4 Reagents: Water
    标题:Ruthenium Amide Complexes - Synthesis And Catalytic Activity In Olefin Metathesis And In Ring-Opening Polymerisation
    作者:Gawin,Anna; Pump,Eva; Slugovc,Christian; Kajetanowicz,Anna; Grela,Karol
    参考文献:European Journal Of Inorganic Chemistry 日期:2018 卷标:2018(16) 页码:1766-1774]

    24424-99-5 = 78839-75-5
    反应条件:1.1 Catalysts: 4-(Dimethylamino)Pyridine Solvents: Tetrahydrofuran; 24 H,Reflux
    标题:One Stone Three Birds: Regiodivergent Access To Amino-Substituted Benzophospholes And Their Structure-Property Relationships
    作者:Zhu,Jiahao; Wang,Lili; Duan,Zheng
    参考文献:Chemrxiv 日期:2022 卷标:1 页码:1-10
📜N-Boc-苯胺置于叔丁基锂,四溴化碳体系中,用 四氢呋喃,正戊烷 作为反应溶剂,化学反应 3.0H,以78%的收率获得产物n-(叔丁氧基羰基)-2-溴苯胺
参考文献:通过有机金属和自由基化学的适当组合,原子核和侧链氟化3-取代的吲哚
标题:通过有机金属和自由基化学的适当组合,原子核和侧链氟化3-取代的吲哚
摘要:使用四步程序制备了区域选择性的氟,三氟甲基和三氟甲氧基取代的3-亚甲基二氢吲哚,所述方法包括氟化/ Boc保护的苯胺的金属化/溴化,所得邻溴代芳基氨基甲酸酯的n-炔丙基化以及产物的还原自由基环化反应.氢化三丁基锡/ Aibn.3-亚甲基二氢吲哚,作为有价值的通用中间体,可以使用不同的亲和剂通过烯类反应转化为高度官能化的3-取代的吲哚.因此,氟-,三氟甲基-和三氟甲氧基取代的2-乙基-2-羟基-2-[((1 H-吲哚-3-基)甲基]丙二酸二乙酯,2-羟基-3-(1 H-吲哚-3-基)乙基丙酸酯和2-羟基-3-(1 H通过简单地加热相应的3-亚甲基吲哚啉-1-羧酸叔丁酯与等摩尔量的酮丁二酸二乙酯,乙二醛酸乙酯和3,3,3-乙基吲哚-3-基)-2-三氟甲基丙酸酯,以77-86%的产率获得.在无溶剂的情况下,分别于100oc和3-三氟丙酮酸0.5-4小时.
DOI:10.1016/j.Jfluchem.2007.09.003

海关参考信息

专利信息


专利号:US-2005192265-A1
优先权日:2003-03-20
标 题:Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds
发明人：THOMPSON RICHARD C; WILKIE STEPHEN; STACK DOUGLAS R; VANMETER ELDON E; SHI QING; BRITTON THOMAS C; AUDIA JAMES E; REEL JON K; MABRY THOMAS E; DRESSMAN BRUCE A; CWI CYNTHIA L; HENRY STEVEN S; MCDANIEL STACEY L; STUCKY RUSSELL D; PORTER WARREN J
摘要:Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions that include a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

专利号:WO-9967219-A1
优先权日:1998-06-22
标 题:Compounds for inhibiting beta-amyloid peptide release and/or its synthesis
发明人：AUDIA JAMES E; PORTER WARREN J; THOMPSON RICHARD C; WILKIE STEPHEN C; STACK DOUGLAS R; SHI QING
权利人:ELAN PHARM INC; LILLY CO ELI; AUDIA JAMES E; PORTER WARREN J; THOMPSON RICHARD C; WILKIE STEPHEN C; STACK DOUGLAS R; SHI QING
摘要:Compounds of formula (I), wherein W is a cyclic group of the type (2); (3); Y is represented by the formula (II); these compounds inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

专利号:WO-9966934-A1
优先权日:1998-06-22
标 题 :CYCLIC AMINO ACID COMPOUNDS, PHARMACEUTICAL COMPOSITIONS COMPRISING SAME, AND METHODS FOR INHIBITING β-AMYLOID PEPTIDE RELEASE AND/OR ITS SYNTHESIS BY USE OF SUCH COMPOUNDS
发明人：AUDIA JAMES E; DRESSMAN BRUCE A; SHI QING
权利人:ELAN PHARM INC; LILLY CO ELI; AUDIA JAMES E; DRESSMAN BRUCE A; SHI QING
摘要:Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

专利号:US-6774125-B2
优先权日:1998-06-22
标 题:Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
发明人：AUDIA JAMES E; THOMPSON RICHARD C; WILKIE STEPHEN C; BRITTON THOMAS C; PORTER WARREN J; HUFFMAN GEORGE W; LATIMER LEE H
权利人:ELAN PHARM INC; LILLY CO ELI
摘要:Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

专利号:US-6509331-B1
优先权日:1998-06-22
标题:Deoxyamino acid compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
发明人：AUDIA JAMES E; THOMPSON RICHARD C; WILKIE STEPHEN C; BRITTON THOMAS C; PORTER WARREN J; HUFFMAN GEORGE W; LATIMER LEE H
权利人:ELAN PHARM INC; LILLY CO ELI
摘要:Disclosed are compounds which inhibit beta-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits beta-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

专利号:US-6849650-B2
优先权日:1998-02-27
标 题:Heterocyclic compounds, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds
发明人：THORSETT EUGENE D; PORTER WARREN J; NISSEN JEFFREY S; LATIMER LEE H; AUDIA JAMES E; DROSTE JAMES
权利人:ATHENA NEUROSCIENCES INC; LILLY CO ELI
摘要:Disclosed are compounds which inhibit β-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits β-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

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主要参考文献

[参考文献]: Yousuke Yamaoka, Et Al. Development Of A Brnsted Acid-Promoted Arene-Ynamide Cyclization Toward The Total Syntheses Of Marinoquinolines A And C And Aplidiopsamine A. J Org Chem. 2015 Jan 16;80(2):957-64.

合成参考文献


摘要:Joule, J. A., Science of Synthesis Knowledge Updates, (2010) 2, 116.
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