Two classes of heterocycles—6,8‐dioxabicyclo[3.2.1]octanes and cyclopentenols from the same reagents: A quantum‐chemical comparison of mechanism

Vitkovskaya Nadezhda M.; Orel Vladimir B.; Kobychev Vladimir B.; Schmidt Elena Yu.; Trofimov Boris A.

摘要

Abstract >Most of the strategies for the synthesis of 6,8‐dioxabicyclo[3.2.1]octanes (BCO) and cyclopentenols (CP), which show high biological and pharmaceutical activity, are multistage and/or require hardly accessible starting materials and catalysts. The general method for BCO and CP preparation in a single preparative stage from two simple reagents, ketones and acetylene, under the action of an available super‐basic catalytic system KOH/DMSO becomes promising for the development of general approaches to the design of these classes of biologically active compounds. The mechanism of competing reactions yielding both 7‐methylene‐6.8‐dioxabicyclo[3.2.1]‐octanes and functionalized cyclopentenoles from their common intermediate 1,5‐diketones and acetylene in the KOH/DMSO superbasic media is investigated using the B2PLYP/6‐311++G**//B3LYP/6‐31+G* calculations with particular attention to the diastereoselectivity aspects of individual stages. </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> >合成6,8-dioxabicyclo的大多数策略[3.2.1]辛烷值（BCO）和环戊烯醇（CP），其显示出高生物和药物活性，是多级的和/或需要几乎无法获得的起始材料和催化剂。在可用超基本催化系统KOH / DMSO的作用下，在两种简单试剂，酮和乙炔的单一制备阶段中BCO和CP制备的一般方法在可用的超碱性催化系统KOH / DMSO的作用下，对这些课程设计的一般方法产生了很大的了解生物活性化合物。使用B2PLYP / 6-研究了来自其常见的中间体1,5-二酮和乙炔的竞争反应的竞争反应的机理和来自其常见的中间体1,5-二酮和乙炔的官能化环戊烯。 311 ++ g ** // b3lyp / 6-31 + g *计算特别注意单个阶段的非对映选择性方面。</ p> </ abstract> </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-21753/'>《International Journal of Quantum Chemistry》</a> <b style="margin: 0 2px;">|</b><span>2018年第18期</span><b style="margin: 0 2px;">|</b><span>共12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=Vitkovskaya Nadezhda M.&option=202" target="_blank" rel="nofollow">Vitkovskaya Nadezhda M.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Orel Vladimir B.&option=202" target="_blank" rel="nofollow">Orel Vladimir B.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kobychev Vladimir B.&option=202" target="_blank" rel="nofollow">Kobychev Vladimir B.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Schmidt Elena Yu.&option=202" target="_blank" rel="nofollow">Schmidt Elena Yu.;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Trofimov Boris A.&option=202" target="_blank" rel="nofollow">Trofimov Boris A.;</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>Laboratory of Quantum ChemistryIrkutsk State University1 K. Marks St. Irkutsk 664003 Russian Federation;</p> <p>Laboratory of Quantum ChemistryIrkutsk State University1 K. Marks St. Irkutsk 664003 Russian Federation;</p> <p>Laboratory of Quantum ChemistryIrkutsk State University1 K. Marks St. Irkutsk 664003 Russian Federation;</p> <p>A.E. Favorsky Irkutsk Institute of Chemistry Siberian Branch of the Russian Academy of Science1 Favorsky St. Irkutsk 664033 Russian Federation;</p> <p>A.E. Favorsky Irkutsk Institute of Chemistry Siberian Branch of the Russian Academy of Science1 Favorsky St. Irkutsk 664033 Russian Federation;</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=acetylene&option=203" rel="nofollow">acetylene;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=cyclopentenols&option=203" rel="nofollow">cyclopentenols;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=density functional theory&option=203" rel="nofollow">density functional theory;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=dioxabicyclooctanes&option=203" rel="nofollow">dioxabicyclooctanes;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=ketones&option=203" rel="nofollow">ketones;</a> </p> <div class="translation"> 机译：乙炔;环戊烯醇;密度函数理论;二恶英酸二辛烷;酮; </div> </li> </ul> </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 class="enjiyixqcontent" href="/journal-foreign-detail/0704019755848.html">Two classes of heterocycles—6,8‐dioxabicyclo[3.2.1]octanes and cyclopentenols from the same reagents: A quantum‐chemical comparison of mechanism</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Vitkovskaya Nadezhda M.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Vitkovskaya Nadezhda M.,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Orel Vladimir B.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Orel Vladimir B.,</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Kobychev Vladimir B.&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">Kobychev Vladimir B.,</a> <a href="/journal-foreign-21753/" target="_blank" rel="nofollow" class="tuijian_authcolor">International Journal of Quantum Chemistry .</a> <span>2018</span><span>,第18期</span> </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：两类杂环-6,8-二恶英[3.2.1]辛烷和来自相同试剂的环戊烯醇：机制的量子化学比较</span> </p> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/journal-foreign-detail/070408345784.html">Quantum chemical study of the formation of acetylenic alcohols and 7-methylidene-6,8-dioxabicyclo[3.2.1]octanes from acetylene and carbonyl compounds</a> <b>[J]</b> . <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=N. 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href="/academic-conference-cn_meeting-58658_thesis/020222806966.html">C<,2>对称二亚砜手性辅助试剂的应用－σ－对称十员氧杂环１，２－二醇的手性非对称化</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=李英霞&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 李英霞</a> <span> <a href="/conference-cn-58658/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 中国第五届海洋湖沼药物学术开发研讨会 </a> <span> <span> . 1998</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/06120104431157.html">8－氮杂二环3.2.1辛烷－,8－氮杂二环3.2.1辛－6－烯,9－氮杂二环3.3.1壬烷－,9－氮杂－３－氧杂二环3.3.1壬烷－,9－氮杂－3－硫杂二环3,3,1壬烷衍生物,其制备方法及其作为杀虫剂的用途</a> <b>[P]</b> . <span> 中国专利： CN1237972A </span> <span> . 1999-12-08</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120108955594.html">作为ASGPR靶向剂的被取代的‑6,8‑二氧杂双环3.2.1辛烷‑2,3‑二醇化合物</a> <b>[P]</b> . <span> 中国专利： CN106459120A </span> <span> . 2017-02-22</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130402265339.html">Substituted 6,8-dioxabicyclo 3.2.1 octane-2,3-diol compounds as ASGPR targeting agents</a> <b>[P]</b> . <span> 外国专利：  JP6663889B2 </span> <span> . 2020-03-13</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：取代6,8-二氧杂双环[3.2.1]辛烷-2,3-二醇化合物作为ASGPR靶向剂 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130403033564.html">SUBSTITUTED-6,8-DIOXABICYCLO 3.2.1.OCTANE-2,3-DIOL COMPOUNDS AS AGENTS AIMED AT ASGPR</a> <b>[P]</b> . <span> 外国专利：  RU2696490C2 </span> <span> . 2019-08-02</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：取代了6,8-二氧杂双环[3.2.1。] OCTANE-2,3-DIOL化合物作为ASGPR的代理商 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130403611965.html">Substituted-6,8-dioxabicyclo3.2.1octane-2,3-diol compounds as targeting agents of ASGPR</a> <b>[P]</b> . <span> 外国专利：  AU2015262993B2 </span> <span> . 2019-11-07</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：取代-6,8-二氧杂双环[3.2.1]辛烷-2,3-二醇化合物作为ASPGR的靶向剂 </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('0704019755848','4',7,2,1,'',this,24)" class="delivery" prompt="010401" 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