Enantiodifferentiating Photodimerization of a 2,6‐Disubstituted Anthracene Assisted by Supramolecular Double‐Helix Formation with Chiral Amines

Urushima Akio; Taura Daisuke; Tanaka Makoto; Horimoto Naomichi; Tanabe Junki; Ousaka Naoki; Mori Tadashi; Yashima Eiji

摘要

Abstract > A novel 2,6‐anthrylene‐linked bis( m ‐terphenylcarboxylic acid) strand ( 1 ) self‐associates into a racemic double‐helix. In the presence of chiral mono‐ and diamines, either a right‐ or left‐handed double‐helix was predominantly induced by chiral amines sandwiched between the carboxylic acid strands with accompanying stacking of the two prochiral anthracene linker units in an enantiotopic face‐selective way, as revealed by circular dichroism and NMR spectral analyses. The photoirradiation of the optically active double helices complexed with chiral amines proceeded in a diastereo‐ ( anti or syn ) and enantiodifferentiating way to afford the chiral anti ‐photodimer with up to 98?% enantiomeric excess when ( R )‐phenylethylamine was used as a chiral double‐helix inducer. The resulting optically active anti ‐photodimer can recognize the chirality of amines and diastereoselectively complex with chiral amines. </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> > 一种新的2,6-三丁烯 - 连接的双（ m </ i> - 苯基羧酸）股线（ 1 </ b> ）自我联系进入外逃双螺旋。在手性单和二胺的存在下，右手或左手双螺旋主要由夹在羧酸股之间的手性胺诱导，其伴随着抗辩生素的面部选择性方式伴随两种培训蒽接头单元的堆叠，正如圆形二中间和核磁共振谱分析所揭示的那样。用手性胺复合的光学活性双螺旋的光放射在非对施 - （反</ i> 或者 syn </ i> ）和孕干的方式负担手性反</ i> - 当时（ R </ I> ） - 苯乙胺用作手性双螺旋诱导剂。由此产生的光学活性反</ i> - 用手性胺识别胺的手感和非对映选择性复杂的胺。 </ 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-19011/'>《Angewandte Chemie》</a> <b style="margin: 0 2px;">|</b><span>2020年第19期</span><b style="margin: 0 2px;">|</b><span>共9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=Urushima Akio&option=202" target="_blank" rel="nofollow">Urushima Akio;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Taura Daisuke&option=202" target="_blank" rel="nofollow">Taura Daisuke;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tanaka Makoto&option=202" target="_blank" rel="nofollow">Tanaka Makoto;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Horimoto Naomichi&option=202" target="_blank" rel="nofollow">Horimoto Naomichi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Tanabe Junki&option=202" target="_blank" rel="nofollow">Tanabe Junki;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Ousaka Naoki&option=202" target="_blank" rel="nofollow">Ousaka Naoki;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Mori Tadashi&option=202" target="_blank" rel="nofollow">Mori Tadashi;</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=Yashima Eiji&option=202" target="_blank" rel="nofollow">Yashima Eiji;</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>Department of Molecular and Macromolecular ChemistryNagoya UniversityChikusa-ku Nagoya 464-8603 Japan;</p> <p>Department of Molecular and Macromolecular ChemistryNagoya UniversityChikusa-ku Nagoya 464-8603 Japan;</p> <p>Department of Molecular Design and EngineeringNagoya UniversityChikusa-ku Nagoya 464-8603 Japan;</p> <p>Department of Molecular Design and EngineeringNagoya UniversityChikusa-ku Nagoya 464-8603 Japan;</p> <p>Department of Molecular Design and EngineeringNagoya UniversityChikusa-ku Nagoya 464-8603 Japan;</p> <p>Department of Molecular and Macromolecular ChemistryNagoya UniversityChikusa-ku Nagoya 464-8603 Japan;</p> <p>Department of Applied ChemistryOsaka University2-1 Yamada-oka Suita Osaka 565-0871 Japan;</p> <p>Department of Molecular and Macromolecular ChemistryNagoya UniversityChikusa-ku Nagoya 464-8603 Japan;</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/1188.html" title="应用化学">应用化学;</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=diastereoselectivity&option=203" rel="nofollow">diastereoselectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=double-helix&option=203" rel="nofollow">double-helix;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=enantioselectivity&option=203" rel="nofollow">enantioselectivity;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=helicity induction&option=203" rel="nofollow">helicity induction;</a> <a style="color: #3E7FEB;" href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=photodimerization reaction&option=203" rel="nofollow">photodimerization reaction;</a> </p> <div class="translation"> 机译：非对接性;双螺旋;对映射性;螺旋感应;光二聚体反应; </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/0704028161962.html">Inside Back Cover: Enantiodifferentiating Photodimerization of a 2,6‐Disubstituted Anthracene Assisted by Supramolecular Double‐Helix Formation with Chiral Amines (Angew. 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class="tuijian_authcolor"> . 人工晶体学报 </a> </span> <span> . 2017</span><span>,第5期</span> </span> </div> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/academic-journal-cn_chemical-journal-chinese-universities_thesis/0201231573028.html">双(二吡啶胺)配体的二维和三维超分子配位聚合物的合成与晶体结构</a> <b>[J]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=丁彩霞&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 丁彩霞</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=曾凡花&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,曾凡花</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=汪成&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,汪成</a> <span> <a href="/journal-cn-10958/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 高等学校化学学报 </a> </span> <span> . 2011</span><span>,第009期</span> </span> </div> </li> <li> <div> <b>6. </b><a class="enjiyixqcontent" href="/academic-conference-cn_meeting-31710_thesis/02022422713.html">一维双螺旋超分子聚合物的合成与结构</a> <b>[C]</b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=翁林红&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 翁林红</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=邹如意&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,邹如意</a> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=冷雪冰&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor">,冷雪冰</a> <span> <a href="/conference-cn-31710/" target="_blank" rel="nofollow" class="tuijian_authcolor"> . 第四届全国配位化学会议 </a> <span> <span> . 2001</span> </span> </div> </li> <li> <div> <b>7. </b><a class="enjiyixqcontent" href="/academic-degree-domestic_mphd_thesis/020313539552.html">侧基带有噁二唑环的苯基取代PPV和聚2，6-蒽基乙烯的合成及性能研究</a> <b>[A] </b> <span> <a href="/search.html?doctypes=4_5_6_1-0_4-0_1_2_3_7_9&sertext=王晓燕&option=202" target="_blank" rel="nofollow" class="tuijian_auth tuijian_authcolor"> . 王晓燕</a> <span> . 2007</span> </span> </div> </li> </ul> <ul style="display: none;"> <li> <div> <b>1. </b><a class="enjiyixqcontent" href="/patent-detail/061201071705.html">酶法制备手性4-取代-2,6-二氧哌啶-3,5-二甲酸单酰胺类化合物的方法</a> <b>[P]</b> . <span> 中国专利： CN101665812B </span> <span> . 2012.12.05</span> </div> </li> <li> <div> <b>2. </b><a class="enjiyixqcontent" href="/patent-detail/06120105864896.html">酶法制备手性4－取代－2，6－二氧哌啶－3，5－二甲酸单酰胺类化合物的方法</a> <b>[P]</b> . <span> 中国专利： CN101665812A </span> <span> . 2010-03-10</span> </div> </li> <li> <div> <b>3. </b><a class="enjiyixqcontent" href="/patent-detail/06130409417195.html">5,15-Bis-pentafluorphenylporphyrin substituted in positions 10 and 20 with perbenzylated sucrose molecules as a substrate of matrix assisted supramolecular chirality amplification and the method of its preparation</a> <b>[P]</b> . <span> 外国专利：  CZ306495B6 </span> <span> . 2017-02-15</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：5,15-双-五氟苯基卟啉在10和20位上被过苄基蔗糖分子取代，作为基质辅助超分子手性扩增的底物及其制备方法 </span> </p> </li> <li> <div> <b>4. </b><a class="enjiyixqcontent" href="/patent-detail/06130412208539.html">Porphyrin substituted in positions 10 and 20 with saccharose molecules and in positions 5 and 15 with phenyl substituents, as harvester of electromagnetic radiation and substrate of matrix-assisted supramolecular amplification of chirality and process for preparing thereof</a> <b>[P]</b> . <span> 外国专利：  CZ2015129A3 </span> <span> . 2016-09-07</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：卟啉在10和20位被蔗糖分子取代，在5和15位被苯基取代基取代，作为电磁辐射的收集物和基质辅助手性超分子扩增的底物及其制备方法 </span> </p> </li> <li> <div> <b>5. </b><a class="enjiyixqcontent" href="/patent-detail/06130412208619.html">Porphyrin substituted in positions 10 and 20 with saccharose molecules and in positions 5 and 15 with phenyl substituents, as harvester of electromagnetic radiation and substrate of matrix-assisted supramolecular amplification of chirality and process for preparing thereof</a> <b>[P]</b> . <span> 外国专利：  CZ20150129A3 </span> <span> . 2016-09-07</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：卟啉在10和20位被蔗糖分子取代，在5和15位被苯基取代基取代，作为电磁辐射的收集物和基质辅助手性超分子扩增的底物及其制备方法 </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: 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