[發(fā)明專利]一種丙二酸二乙酯對(duì)氮雜環(huán)丙烷化合物的開環(huán)方法

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• 申請(qǐng)?zhí)枺?/td>: 201110360339.9
• 申請(qǐng)日: 2011-11-15
• 公開（公告）號(hào): CN102503861A
• 公開（公告）日: 2012-06-20
• 發(fā)明（設(shè)計(jì)）人: 魏文瓏;楊平平;李興;常宏宏;李彥威
• 申請(qǐng)（專利權(quán)）人: 太原理工大學(xué);山西工程職業(yè)技術(shù)學(xué)院
• 主分類號(hào): C07C303/40
• 分類號(hào): C07C303/40;C07C311/20;C07C311/19
• 代理公司: 太原科衛(wèi)專利事務(wù)所(普通合伙) 14100
• 代理人: 戎文華

技術(shù)領(lǐng)域

本發(fā)明涉及一種丙二酸二乙酯對(duì)氮雜環(huán)丙烷化合物的開環(huán)方法，屬于有機(jī)化學(xué)與有機(jī)合成領(lǐng)域。

背景技術(shù)

氮雜環(huán)丙烷是一類具有生物活性的三元雜環(huán)化合物，許多天然產(chǎn)物中含有氮雜環(huán)丙烷組份，它們具有抗病毒、抗腫瘤以及其他生物活性。活化氮雜環(huán)丙烷由于氮原子上連有磺酰基、酰基或膦酰基等吸電子取代基，降低了三元環(huán)上的電子云密度，使其更容易受到親核試劑的進(jìn)攻，在開環(huán)反應(yīng)中表現(xiàn)出較高的活性，可與含碳[(a)Bera?M.,?Roy?S.?Silver(I)-Diene?Complexes?as?Versatile?Catalysts?for?the?C-Arylation?of?N-Tosylaziridines:Mechanistic?Insight?from?In?Situ?Diagnostics[J].?J.?Org.?Chem.,?2010,?75(13):?4402-4412.(b)Hudlicky?T.,Rinner?U.,?Finn?K.?J.,?et?al.?Reactions?of?Indole?Derivatives?with?Oxiranes?and?Aziridines?on?Silica.Synthesis?of?β-Carbolin-1-one?Mimic?of?Pancratistatin[J].?J.?Org.?Chem.?2005,?70(9):?3490-3499.(c)Blyumin?E.?V.,?Gallon?H.?J.,?Yudin?A.?K.?Construction?of?Three?Contiguous?Tertiary?Stereocenters?from?Aziridines?in?One?Step[J].?Organic?Letters,?2007,?9(23):?4677-?4680.(d)Minakata?S.,?Okada?Y.,?Oderaotoshi?Y.,?et?al.?Lewis?Base?Catalyzed?Ring?Opening?of?Aziridines?with?Silylated?Nucleophiles[J].?Org.Lett.,?2005,?7(16):?3509-3512.(e)Hayashi?Y.,?Kumamoto?T.,?Kawahata?M.,?et?al.?Ring-Opening?Reaction?of?Unactivated?3-Arylaziridine-2-Carboxylates?with?Nitrile?Reagents[J].?Tetrahedron,?2010,?66(21):?3836-3841.(f)Mita?T.,?Fujimori?I.,?Wada?R.,?et?al.?Catalytic?Enantioselective?Desymmetrization?of?meso-N-Acylaziridines?with?TMSCN[J].?J.?Am.?Chem.?Soc.,?2005,?127(32):?11252?-?11253.]、氮[(a)Parrodi?C.?A.,?Vázquez?V.,?Quintero?L.,?et?al.?Trans-1,2-Diaminocyclohexane?Deriva-?tives?by?Lithium?Perchlorate?Catalyzed?Ring?Opening?of?Aziridines?[J].?Synthetic?Com?-munications,?2001,?31(21):?3295-3302.(b)Chandrasekhar?M.,?Sekar?G.,?Singh?V.?K.?An?Ef?cient?Method?for?Opening?Nonacti-?vated?Aziridines?with?TMS?Azide:Application?in?the?Synthesis?of?Chiral?1,2-Diamino-?cyclohexane[J].?Tetrahedron?Letters,?2000,?41(51):?10079-10083.(c)Yadav?J.?S.,?Reddy?B.?V.?S.,?Sadashiv?K.,?et?al.?Montmorillonite?KSF/SiO₂?as?Novel?and?Recyclable?Solid?Acids?for?the?Synthesis?of?β-Aminohalides?and?β-Azidoamines[J].?Catalysis?Communications,?2004,?5(3):?111-114.(d)Peruncheralathan?S.,?Henze?M.,?Schneider?C.?Scandium?Triflate?Catalyzed?Aminolysis?of?meso-Aziridines[J].?Synlett,?2007,?2007(14):?2289-2291.]、氧[(a)Wang?Z.,?Cui?Y.?T.,?Xu?Z.?B.,?et?al.?Hot?Water-Promoted?Ring-Opening?of?Epoxides?and?Aziridines?by?Water?and?Other?Nucleopliles[J].?J.?Org.?Chem.,?2008,?73(6):?2270?-2274.(b)Liu?Y.?K.,?Li?R.,?Yue?L.,?et?al.?Unexpected?Ring-Opening?Reactions?of?Aziridines?with?Aldehydes?Catalyzed?by?Nucleophilic?Carbenes?under?Aerobic?Conditions[J].?Org.?Lett.,?2006,?8(8):?1521-1524.]、硫[(a)Kamal?A.,?Reddy?D.?R.,?Rajendar.?Polyethylene?Glycol?(PEG)?as?an?Efficient?Recycl-?able?Medium?for?the?Synthesis?of?β-Amino?Sul?des[J].?Tetrahedron?Letters,?2006,?47?(13):?2261-2264.(b)Yadav?J.?S.,?Reddy?B.?V.?S.,?Jyothirmai?B.,?et?al.?Lithium?Perchlorate-Catalyzed?Regio-?selective?Ring-Opening?of?Aziridines?with?Potassium?Thiocyanate[J].?Tetrahedron?Letters,?2005,?46(37):?6385-6387.]、鹵素[(a)Ghorai?M.?K.,?Kumar?A.,?Tiwari?D.?P.?BF₃·OEt₂-Mediated?Highly?Regioselective?SN₂-?Type?Ring-Opening?of?N-Activated?Aziridines?and?N-Activated?Azetidines?by?Tetra-?alkylammonium?Halides[J].?J.?Org.?Chem.,?2010,?75(1):?137-151.]等各種親核試劑發(fā)生開環(huán)反應(yīng)生成含有不同官能團(tuán)的胺、氨基酸、氨基硫醇以及其他生物活性的化合物，因此氮雜環(huán)丙烷的開環(huán)反應(yīng)越來(lái)越受到有機(jī)化學(xué)研究者的關(guān)注與重視。