CAS: 10087-64-6; 1H,1'H-2,2'-Bipyrrole

该化合物是由两个位于两处的火花环组成的一个环环形有机化合物, 具有独特的电子和协调特性, 使其在化学和材料科学的协调中具有价值. 它的同质系统可以应用有机半导体, 光电装置和金属综合体的离子体. 该复合体的硬性, 平面几何测量法促进了堆叠的强烈相互作用, 增强上层分子组件的稳定性. 此外, 2, 2'-Bipyrorole 成为合成更复杂的多温极素衍生物的前体, 这对于导体聚合物和感应技术十分有利. 它的多功能性和再活性使其成为先进的化学研究和工业应用中的有用建筑块.

结构式图片

相似化合物

17285-54-0 366-18-7 16576-78-6

合成工艺路线路线简述

  • 合成目标产物 2,2'-Bipyrrol 主要起始原料 Acetamide, N-[[4,5-Dihydro-3-(1H-Pyrrol-2-yl)-5-Isoxazolyl]Methyl]-
  • (文献来源)合成步骤主要原料 Acetamide, N-[[4,5-Dihydro-3-(1H-Pyrrol-2-yl)-5-Isoxazolyl]Methyl]-
📜吡咯置于[双(三氟乙酰氧基)碘]苯 三甲基溴硅烷体系中,用 二氯甲烷 用作溶剂,以78%的收率获得2,2'-二吡咯
参考文献:使用 Phenyliodine (III) Bis(Trifluoroacetate) 的吡咯和 3-取代吡咯的区域选择性双吡咯偶联
标题:使用 Phenyliodine (III) Bis(Trifluoroacetate) 的吡咯和 3-取代吡咯的区域选择性双吡咯偶联
摘要:在溴代三甲基硅烷存在下,通过区域选择性的苯碘(III)双(三氟乙酸)(pifa)诱导吡咯的氧化偶联制备了一系列富电子联吡咯.使用吡咯和 3,4-二取代吡咯仅得到 2,2'-连接的联吡咯,而不会形成其他联吡咯区域异构体.3-烷基或3-芳基取代的吡咯以高产率产生不对称的ht二聚体,作为对称hh二聚体上主要的可分离α-连接的联吡咯产物.N-取代基的性质显着影响反应的区域选择性,因此n-苯基-和n-苄基-取代的吡咯的区域控制联吡咯偶联得到2,3'-联吡咯.
Doi:10.1055/s-2007-983798

专利信息


专利号:US-6162882-A
优先权日:1996-07-10
标 题:Preparation of novel homo- and copolymers using atom transfer radical polymerization
发明人:MATYJASZEWSKI KRZYSZTOF; COCA SIMION; GAYNOR SCOTT G; NAKAGAWA YOSHIKI; JO SEONG MU
权利人:UNIV CARNEGIE MELLON
摘要:The present invention is directed to a process of atom (or group) transfer radical polymerization for the synthesis of novel homopolymer or a block or graft copolymer, optionally containing at least one polar group, with well defined molecular architecture and narrow polydipersity index, in the presence of an initiating system comprising (i) an initiator having a radically transferrable atom or group, (ii) a transition metal compound, and (iii) a ligand, the present invention is also directed to the synthesis of a macromolecule having at least two halogen groups which can be used as a macroinitiator component (i) to subsequently form a block or graft copolymer by an atom or group transfer radical polymerization process; the present invention is also directed to a process of atom or group transfer radical polymerization for the synthesis of a branched or hyperbranched polymer; in addition, the present invention is directed to a process of atom or group transfer radical polymerization for the synthesis of a macroinitiator which can subsequently be used to produce a block or graft copolymer.

专利号:US-9379335-B2
优先权日:2012-04-08
标题:Benzodipyrrolidones and their polymers: synthesis and applications for organic electronics and optoelectronics
发明人:CUI WEIBIN; WUDL FRED
权利人:UNIV CALIFORNIA
摘要:Disclosed is the synthesis of benzodipyrrolidone and their polymers and small molecules for electronic and optoelectronic applications. Also disclosed are devices that incorporate such polymers and small molecules.

专利号:US-8653231-B2
优先权日:2007-05-31
标题:Synthesis of conducting polymer nanofibers using an oligomer of a monomer as an initiator
发明人:KANER RICHARD B; SHIN KOO; TRAN HENRY HIEP D
权利人:KANER RICHARD B; SHIN KOO; TRAN HENRY HIEP D; UNIV CALIFORNIA
摘要:The present invention involves synthesizing conducting polymer nanofibers by mixing an oxidant solution with a monomer solution, which includes a monomer and an oligomer of the monomer that is used as an initiator. The oxidant solution includes an oxidizing agent, or oxidant, such as ferric chloride to oxidize the monomer, the oligomer, or both, and begin polymerization. By including an initiator in the form of the oligomer, which may have a lower oxidation potential than the monomer, the rate of polymerization is accelerated, resulting in the nanofibrous morphology. Therefore, the conducting polymer nanofibers may be synthesized without the use of surfactants, hard templates, or seeds, resulting in a simplified and accelerated polymerization process, which enhances homogenous nucleation of the conducting polymer nanofibers.

专利号:US-7112671-B2
优先权日:2000-08-30
标 题 :Non-symmetric tripyrranes in the synthesis of novel macrocycles
发明人:MODY TARAK D; GALANTER JOSHUA
权利人:PHARMACYCLICS INC
摘要:The present invention provides certain non-symmetric tripyrranes; that is, tripyrranes that do not contain a mirror plane of symmetry perpendicular to the plane containing the tripyrrane. Further, the invention includes texaphyrin compounds and sapphyrin compounds, as well as other polypyrrolic macrocycles, prepared using tripyrranes of Formula I as a precursor. These macrocycles are characterized by a tripyrrolic portion of the macrocyclic ring having substituents that cause the heterocycle to lack a plane of symmetry perpendicular to the plane of the macrocycle.

专利号:WO-0196313-A1
优先权日:2000-06-14
标 题:Distamycin a analogs
发明人:BOGER DALE L
权利人:SCRIPPS RESEARCH INST; BOGER DALE L
摘要:The development of a solution-phase synthesis of distamycin A and its extension to the preparation of 2640 analogs are described. Thus, solution-phase synthesis techniques with reaction workup and purification employing acid/base liquid-liquid extractions were used in the multistep preparation of distamycin A (8 steps, 40 % overall yield) and a prototypical library of 2640 analogs providing intermediates and final products that are ≥ 95 % pure on conventional reaction scales. Screening the prototypical library provided compounds that are 1000 times more potent than distamycin A in cytotoxic assays (67, IC50 = 29 nM, L1210), that bind to poly[dA]-poly[dT] with comparable affinity, and that exhibit an altered DNA binding sequence selectivity. Several candidates were identified which bound the five base-pair AT-rich site of the PSA-ARE-3 sequence, and one (128, K = 3.2 x 106 M-1) maintained the high affinity binding (K = 4.5 x 106 M-1) to the ARE-consensus sequence containing a GC base-pair interrupted five base-pair AT-rich site suitable for inhibition of gene transcription initiated by hormone insensitive androgen receptor dimerization and DNA binding characteristic of therapeutic resistant prostate cancer.

专利号:US-5622945-A
优先权日:1992-08-04
标题 :Rubyrin macrocycles
发明人:SESSLER JONATHAN L; MORISHIMA TAKASHI; WEGHORN STEVEN J
权利人:UNIV TEXAS
摘要:The present invention is directed to the synthesis and use of novel macrocyclic compounds, based upon a new class of expanded porphyrins, termed rubyrins. Disclosed herein is the structure and synthesis of a prototypical rubyrin and various substituted rubyrin analogues, conjugates and compositions. Rubyrin itself is characterized by the presence of six pyrrolic subunits contained within a fully aromatic 26 Ï€-electron macrocyclic framework and by UV/VIS absorption bands that are very red-shifted as compared to those of other porphyrins or pentapyrrolic expanded porphyrins. The rubyrin-type class of compounds is further characterized by an ability to undergo facile protonation at the pyrrolic nitrogens and, once protonated, by an ability to form complexes with anions such as nucleotide-containing compounds. Rubyrin-based compounds are useful as, for example, anion chelators and receptors and as transporters for various anionic compounds including antiviral agents. In addition to the 26 Ï€-electron target system, the present invention concerns other oxidation states bearing the same connectivity and the same total number of non-hydrogen atoms, and various analogues in which different substituents are present at the various meso and/or β-pyrrolic positions or in which furan and/or thiophene moieties replace one or more of the six pyrrolic subunits.

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合成参考文献


摘要:Logeswaran, R.; Aravindan, N.; Jeganmohan, M., Science of Synthesis: Cross-Dehydrogenative Coupling, (2023) nan, 30.
参考文献:10.1007/bf02269486
摘要:Shemin D. The biosynthesis of porphyrins. Ergebnisse der Physiologie und exper. Pharmakologie. 1957 Dec;49(1):299–326. doi: 10.1007/bf02269486.
参考文献:10.1007/s00775-017-1444-5
摘要:Wang J, Ma F, Sun H, Zhang J, Zhang J. Three bilindione isomers: synthesis, characterization and reactivity of biliverdin analogs. JBIC Journal of Biological Inorganic Chemistry. 2017 Feb 07;22(5):727–37. doi: 10.1007/s00775-017-1444-5.
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