伪装的硼：双亲“融合”的 BN 吲哚。
Boron in disguise: the parent "fused" BN indole.
机构信息
Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.
出版信息
J Am Chem Soc. 2011 Aug 3;133(30):11508-11. doi: 10.1021/ja205779b. Epub 2011 Jul 13.
Abstract
"Fused" BN indoles are an emerging class of boron-containing indole mimics, featuring geometric structure and electophilic aromatic substitution reactivity similar to those of indoles but exhibiting distinct electronic structure, leading to unique optoelectronic properties. Herein we report the synthesis of the parent N-H BN indole and provide a head-to-head comparison of the structural features, pK(a) values, and optoelectronic properties of this hybrid organic/inorganic indole with the classic natural indole.
摘要
“融合” BN 吲哚是一类新兴的含硼吲哚类似物，具有与吲哚相似的几何结构和亲电芳香取代反应性，但表现出独特的电子结构，从而具有独特的光电性能。在此，我们报告了 N-H BN 吲哚的合成，并对该杂化有机/无机吲哚与经典天然吲哚的结构特征、pK(a) 值和光电性能进行了直接比较。
相似文献
1
Boron in disguise: the parent "fused" BN indole.伪装的硼：双亲“融合”的 BN 吲哚。
J Am Chem Soc. 2011 Aug 3;133(30):11508-11. doi: 10.1021/ja205779b. Epub 2011 Jul 13.
2
UV-photoelectron spectroscopy of BN indoles: experimental and computational electronic structure analysis.氮化硼吲哚的紫外光电子能谱：实验与计算电子结构分析
J Am Chem Soc. 2014 Aug 20;136(33):11813-20. doi: 10.1021/ja5063899. Epub 2014 Aug 11.
3
Electrophilic aromatic substitution of a BN indole.硼氮吲哚的亲电芳香取代反应。
J Am Chem Soc. 2010 Nov 24;132(46):16340-2. doi: 10.1021/ja107312u. Epub 2010 Nov 2.
4
BN isosteres of indole.吲哚的 BN 等排体。
Org Biomol Chem. 2013 Apr 7;11(13):2060-9. doi: 10.1039/c3ob27436e.
5
Electric Dipole Transition Moments and Solvent-Dependent Interactions of Fluorescent Boron-Nitrogen Substituted Indole Derivatives.荧光硼氮取代吲哚衍生物的电偶极跃迁矩及溶剂依赖性相互作用
J Phys Chem B. 2015 Jun 25;119(25):7985-93. doi: 10.1021/acs.jpcb.5b03485. Epub 2015 Jun 3.
6
Three-component domino reactions for regioselective formation of bis-indole derivatives.三组分多米诺反应用于区域选择性地形成双吲哚衍生物。
ACS Comb Sci. 2013 Feb 11;15(2):135-40. doi: 10.1021/co3001428. Epub 2013 Jan 31.
7
Synthesis of fused 4,5-disubstituted indole ring systems by intramolecular friedel-crafts acylation of 4-substituted indoles.通过4-取代吲哚的分子内傅克酰基化反应合成稠合的4,5-二取代吲哚环系统。
J Org Chem. 2008 Apr 4;73(7):2920-3. doi: 10.1021/jo702591p. Epub 2008 Mar 6.
8
Cyclohepta[b]indoles: A Privileged Structure Motif in Natural Products and Drug Design.环庚[b]吲哚类化合物：天然产物和药物设计中的一个优势结构基序。
Acc Chem Res. 2016 Nov 15;49(11):2390-2402. doi: 10.1021/acs.accounts.6b00265. Epub 2016 Oct 6.
9
Synthesis of indole analogues of the natural schweinfurthins.吲哚类似物的合成天然schweinfurthins。
J Org Chem. 2013 Sep 20;78(18):9291-302. doi: 10.1021/jo4014244. Epub 2013 Sep 5.
10
Brønsted acid catalyzed enantioselective indole aza-Claisen rearrangement mediated by an arene CH-O interaction.布朗斯特酸催化的通过芳基 CH-O 相互作用介导的吲哚氮杂-Claisen 重排的对映选择性。
J Am Chem Soc. 2013 Nov 6;135(44):16380-3. doi: 10.1021/ja4095473. Epub 2013 Oct 28.
引用本文的文献
1
From propenolysis to enyne metathesis: tools for expedited assembly of 4,8-azaboranaphthalene and extended polycycles with embedded BN.从丙烯醇解到烯炔复分解：用于快速组装4,8-氮杂硼萘和含嵌入BN的扩展多环化合物的工具
Chem Sci. 2024 Mar 7;15(15):5674-5680. doi: 10.1039/d3sc06676b. eCollection 2024 Apr 17.
2
Isosterism in pyrrole via azaboroles substitution, a theoretical investigation for electronic structural, stability and aromaticity.通过氮杂硼环戊二烯取代实现吡咯中的等电子体，关于电子结构、稳定性和芳香性的理论研究
Heliyon. 2023 Sep 29;9(10):e20542. doi: 10.1016/j.heliyon.2023.e20542. eCollection 2023 Oct.
3
BN-Substitution in Dithienylpyrenes Prevents Excimer Formation in Solution and in the Solid State.二噻吩并芘中的硼氮取代可防止溶液和固态中的激基缔合物形成。
J Phys Chem C Nanomater Interfaces. 2022 Mar 10;126(9):4563-4576. doi: 10.1021/acs.jpcc.1c08812. Epub 2022 Feb 24.
4
Selectivity in the Elaboration of Bicyclic Borazarenes.双环硼氮杂苯合成中的选择性
Adv Synth Catal. 2021 Apr 27;363(9):2256-2273. doi: 10.1002/adsc.202001384. Epub 2020 Dec 23.
5
Computational studies on nitro derivatives of BN indole as high energetic material.作为高能材料的硼氮吲哚硝基衍生物的计算研究。
J Mol Model. 2020 Mar 24;26(4):83. doi: 10.1007/s00894-020-4337-4.
6
Cation-π binding ability of BN indole.硼氮吲哚的阳离子-π 键结合能力。
Chem Commun (Camb). 2020 Mar 31;56(26):3749-3752. doi: 10.1039/d0cc00869a.
7
Synthesis and characterization of an unnatural boron and nitrogen-containing tryptophan analogue and its incorporation into proteins.一种非天然含硼和氮的色氨酸类似物的合成、表征及其在蛋白质中的掺入。
Chem Sci. 2019 Apr 15;10(19):4994-4998. doi: 10.1039/c8sc05167d. eCollection 2019 May 21.
8
Site-Selective and Stereoselective trans-Hydroboration of 1,3-Enynes Catalyzed by 1,4-Azaborine-Based Phosphine-Pd Complex.基于 1,4-氮杂硼烷的膦-钯配合物催化的 1,3-烯炔的位点选择性和立体选择性反式硼氢化反应。
J Am Chem Soc. 2016 Nov 9;138(44):14566-14569. doi: 10.1021/jacs.6b09759. Epub 2016 Nov 1.
9
Synthesis of Functionalized 1,3,2-Benzodiazaborole Cores Using Bench-Stable Components.使用易于储存的组分合成功能化的1,3,2-苯并二氮杂硼戊环核心结构。
J Org Chem. 2016 May 6;81(9):3771-9. doi: 10.1021/acs.joc.6b00435. Epub 2016 Apr 12.
10
Electric Dipole Transition Moments and Solvent-Dependent Interactions of Fluorescent Boron-Nitrogen Substituted Indole Derivatives.荧光硼氮取代吲哚衍生物的电偶极跃迁矩及溶剂依赖性相互作用
J Phys Chem B. 2015 Jun 25;119(25):7985-93. doi: 10.1021/acs.jpcb.5b03485. Epub 2015 Jun 3.
本文引用的文献
1
Resonance stabilization energy of 1,2-azaborines: a quantitative experimental study by reaction calorimetry.1,2-氮杂硼烷的共振稳定能：通过反应量热法的定量实验研究。
J Am Chem Soc. 2010 Dec 29;132(51):18048-50. doi: 10.1021/ja109596m. Epub 2010 Dec 8.
2
Electrophilic aromatic substitution of a BN indole.硼氮吲哚的亲电芳香取代反应。
J Am Chem Soc. 2010 Nov 24;132(46):16340-2. doi: 10.1021/ja107312u. Epub 2010 Nov 2.
3
Synthesis, characterization, and binding property of isoelectronic analogues of nucleobases, B(6)-substituted 5-aza-6-borauracils and -thymines.碱基等电子类似物的合成、表征及结合特性：B（6）取代的 5-氮杂-6-硼尿嘧啶和胸腺嘧啶。
Org Lett. 2010 Aug 6;12(15):3386-9. doi: 10.1021/ol1012058.
4
Microwave spectrum, structural parameters, and quadrupole coupling for 1,2-dihydro-1,2-azaborine.1,2-二氢-1,2-氮杂硼烷的微波谱、结构参数和四极耦合。
J Am Chem Soc. 2010 Apr 21;132(15):5501-6. doi: 10.1021/ja1005338.
5
Molecular double-bond covalent radii for elements Li-E112.元素 Li-E112 的分子双键共价半径。
Chemistry. 2009 Nov 23;15(46):12770-9. doi: 10.1002/chem.200901472.
6
How stable are 1,2-dihydro-1,2-azaborines toward water and oxygen?1,2 - 二氢 - 1,2 - 氮杂硼烷对水和氧气的稳定性如何？
Mol Biosyst. 2009 Nov;5(11):1303-5. doi: 10.1039/b904120f. Epub 2009 Aug 10.
7
Boron mimetics: 1,2-dihydro-1,2-azaborines bind inside a nonpolar cavity of T4 lysozyme.硼模拟物：1,2-二氢-1,2-氮杂硼烷结合在T4溶菌酶的非极性腔内。
Angew Chem Int Ed Engl. 2009;48(37):6817-9. doi: 10.1002/anie.200903390.
8
Reassessment of the reaction mechanism in the heme dioxygenases.对血红素双加氧酶反应机制的重新评估。
J Am Chem Soc. 2009 Apr 1;131(12):4186-7. doi: 10.1021/ja808326g.
9
A hybrid organic/inorganic benzene.
Angew Chem Int Ed Engl. 2009;48(5):973-7. doi: 10.1002/anie.200805554.
10
Effect of periodic replacement of the heteroatom on the spectroscopic properties of indole and benzofuran derivatives.杂原子的周期性置换对吲哚和苯并呋喃衍生物光谱性质的影响。
J Phys Chem A. 2009 Jan 15;113(2):464-73. doi: 10.1021/jp8079843.
Zotero 插件