Squaramide‐IRMOF‐16 Analogue for Catalysis of Solvent‐Free, Epoxide Ring‐Opening Tandem and Multicomponent Reactions

Vignatti Claudia; Luis‐Barrera Javier; Guillerm Vincent; Imaz Inhar; Mas‐Ballesté Rubén; Alemán José; Maspoch Daniel

摘要

Abstract >Tandem and multicomponent one‐pot reactions are highly attractive because they enable synthesis of target molecules in a single reaction vessel. However, they are difficult to control, as they can lead to the formation of many undesired side‐products. Herein we report the use of metal‐organic framework (MOF) pores decorated with organocatalytic squaramide moieties to confine ring‐opening epoxide reactions of diverse substrates. Controlled mono‐addition or tandem reactions inside the pores yield 1,2‐aminoalcohols or 1,2,2′‐aminodialcohols, respectively, in good yields. In addition, this squaramide‐functionalised MOF enables catalysis of higher‐complexity multicomponent reactions such as the catalytic ring‐opening of two different epoxides by a single amine to afford 1,2,2′‐aminodialcohols. </abstract> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> <div class="translation abstracttxt"> <span class="zhankaihshouqi fivelineshidden" id="abstract"> <span>机译：</span><Abstract Type =“Main”XML：Lang =“en”> <标题类型=“main”>抽象</ title> >串联和多组分的单壶反应非常有吸引力，因为它们能够在单一反应容器中合成靶分子。然而，它们难以控制，因为它们可以导致形成许多不期望的侧面产品。在此，我们报告了使用有机催化鳞状物品装饰的金属有机骨架（MOF）孔隙，以限制各种底物的开环环氧化物反应。在孔内控制单加入或串联反应，分别以良好的产率分别产生1,2-氨基醇或1,2,2'-氨基醇。此外，这种Squaramide官能化MOF能够通过单个胺作为催化开环的催化环，例如通过单胺得到两种不同环氧化物的催化开环，得到1,2,2'-氨基醇。</ p> </摘要> </span> <span class="z_kbtn z_kbtnclass hoverxs" style="display: none;">展开▼</span> </div> </div> <div class="record"> <h2 class="all_title" id="enpatent33" >著录项</h2> <ul> <li> <span class="lefttit">来源</span> <div style="width: 86%;vertical-align: text-top;display: inline-block;"> <a href='/journal-foreign-16041/'>《ChemCatChem》</a> <b style="margin: 0 2px;">|</b><span>2018年第18期</span><b style="margin: 0 2px;">|</b><span>共4页</span> </div> </li> <li> <div class="author"> <span class="lefttit">作者</span> <p id="fAuthorthree" class="threelineshidden zhankaihshouqi"> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Vignatti Claudia&option=202" target="_blank" rel="nofollow">Vignatti Claudia;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Luis‐Barrera Javier&option=202" target="_blank" rel="nofollow">Luis‐Barrera Javier;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Guillerm Vincent&option=202" target="_blank" rel="nofollow">Guillerm Vincent;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Imaz Inhar&option=202" target="_blank" rel="nofollow">Imaz Inhar;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Mas‐Ballesté Rubén&option=202" target="_blank" rel="nofollow">Mas‐Ballesté Rubén;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Alemán José&option=202" target="_blank" rel="nofollow">Alemán José;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Maspoch Daniel&option=202" target="_blank" rel="nofollow">Maspoch Daniel;</a> </p> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zkzz" style="display: none;">展开▼</span> </div> </li> <li> <div style="display: flex;"> <span class="lefttit">作者单位</span> <div style="position: relative;margin-left: 3px;max-width: 639px;"> <div class="threelineshidden zhankaihshouqi" id="fOrgthree"> <p>Catalan Institute of Nanoscience and Nanotechnology (ICN2)CSIC and The Barcelona Institute of Science and TechnologyCampus UAB Bellaterra 08193 Barcelona Spain;</p> <p>Organic Chemistry Department Módulo 1Universidad Autónoma de MadridMadrid- 28049 Spain;</p> <p>Catalan Institute of Nanoscience and Nanotechnology (ICN2)CSIC and The Barcelona Institute of Science and TechnologyCampus UAB Bellaterra 08193 Barcelona Spain;</p> <p>Catalan Institute of Nanoscience and Nanotechnology (ICN2)CSIC and The Barcelona Institute of Science and TechnologyCampus UAB Bellaterra 08193 Barcelona Spain;</p> <p>Inorganic Chemistry DepartmentUniversidad Autónoma de MadridMadrid- 28049 Spain;</p> <p>Organic Chemistry Department Módulo 1Universidad Autónoma de MadridMadrid- 28049 Spain;</p> <p>Catalan Institute of Nanoscience and Nanotechnology (ICN2)CSIC and The Barcelona Institute of Science and TechnologyCampus UAB Bellaterra 08193 Barcelona Spain;</p> </div> <span class="z_kbtnclass z_kbtnclassall hoverxs" id="zhdw" style="display: none;">展开▼</span> </div> </div> </li> <li > <span class="lefttit">收录信息</span> <span style="width: 86%;vertical-align: text-top;display: inline-block;"></span> </li> <li> <span class="lefttit">原文格式</span> <span>PDF</span> </li> <li> <span class="lefttit">正文语种</span> <span>eng</span> </li> <li> <span class="lefttit">中图分类</span> <span><a href="https://www.zhangqiaokeyan.com/clc/1186.html" title="物理化学（理论化学）、化学物理学">物理化学（理论化学）、化学物理学;</a></span> </li> <li class="antistop"> <span class="lefttit">关键词</span> <p style="width: 86%;vertical-align: text-top;"> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Metal-organic frameworks&option=203" rel="nofollow">Metal-organic frameworks;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=H-bond catalysis&option=203" rel="nofollow">H-bond catalysis;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tandem and multicomponent reactions&option=203" rel="nofollow">Tandem and multicomponent reactions;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Squaramide&option=203" rel="nofollow">Squaramide;</a> </p> <div class="translation"> 机译：金属有机框架;H键催化;串联和多组分反应;鳞状; </div> </li> </ul> </div> </div> <div class="literature cardcommon" id="literaturereference" style="display:none"> <div class="similarity "> <h3 class="all_title" id="enpatent111">引文网络</h3> <div class="referencetab clearfix"> <ul id="referencedaohang"> <li dataid="referenceul">参考文献</li> <li dataid="citationul">引证文献</li> <li dataid="commonreferenceul">共引文献</li> <li dataid="commoncitationul">同被引文献</li> <li dataid="tworeferenceul">二级参考文献</li> <li dataid="twocitationul">二级引证文献</li> </ul> </div> <div class="reference_details" id="referenceList"> <ul id="referenceul"></ul> <ul id="citationul"></ul> <ul id="commonreferenceul"></ul> <ul id="commoncitationul"></ul> <ul id="tworeferenceul"></ul> <ul id="twocitationul"></ul> </div> </div> </div> <div class="literature cardcommon"> <div class="similarity "> <h3 class="all_title" id="enpatent66">相似文献</h3> <div class="similaritytab clearfix"> <ul> <li class="active" >外文文献</li> <li >中文文献</li> <li >专利</li> </ul> </div> <div class="similarity_details"> <ul > <li> <div> <b>1. </b><a 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class="tuijian_auth tuijian_authcolor">,史庆伟</a> <span> <a href="/journal-cn-7881/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 石油化工 </a> </span> <span> . 2021</span><span>,第005期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-35748_thesis/020221350911.html">环丙基膦酸酯及环丙基氧化膦与亲核试剂的开环反应</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=张荣馀&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 张荣馀</a> <span> <a href="/conference-cn-35748/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第三届全国磷化学学术讨论会 </a> <span> <span> . 1994</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020312273331.html">酸催化下的2-酰基-1-苯氧基环丙基甲酸酯的开环串联反应研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=徐盼盼&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 徐盼盼</a> <span> . 2017</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061203533472.html">一种用于环烯烃开环聚合的催化体系以及环烯烃开环聚合的方法</a> <b>[P]</b> . <span> 中国专利： CN107200803B </span> <span> . 2019.11.12</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120109685640.html">一种用于环烯烃开环聚合的催化体系以及环烯烃开环聚合的方法</a> <b>[P]</b> . <span> 中国专利： CN107200803A </span> <span> . 2017-09-26</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130450887551.html">Process to produce a polymer or copolemer from a monomer consisting of an acrylate, methacrylate or a mixture of such monomers, resin made by it, process for mass polymerisation for the preparation of poly (butyl acrylate co-acrylate of 2-ethylhexyla),solvent free resin, mass polymerisation process for the preparation of solvent-free poly (butyl acrylate co-acrylate with 2-ethyl hexyla) substantially solvent-free poly (butyl acrylate with co-acrylate with 2-ethylhexyla) free, process comprising a step to cover articles of manufacture with a resin composition, articles of manufacture, solvent-free polymerised reaction product, mass polymerisation process for the preparation of polymer or copolemer substantially solvent-free, and product made by the solvent</a> <b>[P]</b> . <span> 外国专利：  BR9814831A </span> <span> . 2000-10-03</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：由丙烯酸酯，甲基丙烯酸酯或这些单体的混合物组成的单体生产聚合物或共聚物的方法，由其制得的树脂，本体聚合制备聚（丙烯酸2-乙基己基酯的丙烯酸丁酯）的方法，溶剂不含树脂的本体聚合方法，用于制备不含溶剂的聚（丙烯酸丁酯和2-乙基己基丙烯酸酯共丙烯酸酯），基本上不含溶剂的聚丙烯酸丁酯和带有2-乙基己基丙烯酸酯共丙烯酸酯的方法，该方法包括以下步骤：涵盖具有树脂组合物的制品，制品，无溶剂的聚合反应产物，用于制备基本上无溶剂的聚合物或共聚物的大规模聚合方法以及由溶剂制得的产物 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130429260491.html">A process for the solvent-free continuous production of tin-free reaction products of hydroxyl-containing, carbonyl, hydrogenated ketone - aldehyde resins and / or hydrogenated ketone resins and / or carbonyl, hydrogenated and ring-hydrogenated ketone - aldehyde resins based on aromatic ketones and polyisocyanates, the produced products and their use</a> <b>[P]</b> . <span> 外国专利：  DE102007063350A1 </span> <span> . 2009-03-05</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：一种无溶剂连续生产基于芳族化合物的含羟基，羰基，氢化酮醛树脂和/或氢化酮树脂和/或羰基，氢化和环氢化酮醛树脂的无锡反应产物的无溶剂连续生产方法酮和多异氰酸酯，生产的产品及其用途 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130414769648.html">PREPARATION OF ENANTIOPURE VICINAL DIOLS AND ALPHA-HYDROXYKETONES FROM RACEMIC AND MESO-EPOXIDES BY TANDEM BIOCATALYSIS VIA ENANTIOSELECTIVE HYDROLYSIS AND OXIDATIONS</a> <b>[P]</b> . <span> 外国专利：  WO2014209230A1 </span> <span> . 2014-12-31</span> </div> <p class="zwjiyix translation" style="max-width: initial;height: auto;word-break: break-all;white-space: initial;text-overflow: initial;overflow: initial;"> <span>机译：通过串联生物催化从对映体和内环氧化物制备对映体二酚和α-羟基酮的对映体选择性水解和氧化 </span> </p> </li> </ul> </div> </div> </div> <div class="theme cardcommon" style="overflow: auto;display:none"> <h3 class="all_title" id="enpatent55">相关主题</h3> <ul id="subject"> </ul> </div> </div> </div> </div> <div class="right rightcon"> <div class="details_img cardcommon clearfix" style="margin-bottom: 10px;display:none;" > </div> </div> </div> <div id="thesis_get_original1" class="downloadBth" style="bottom: 19px;z-index: 999;" onclick="ywcd('0704022056999','4',7,2,1,'',this,24)" class="delivery" prompt="010401" title="通过人工服务将文献原文发送至邮箱" >获取原文</div> <div class="journalsub-pop-up" style="display: none"> <div class="journal-sub"> <h2>期刊订阅</h2> <img 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