2-bromo-1-phenyl-1H-pyrrole | 30068-53-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-bromo-1-phenyl-1H-pyrrole
• 英文别名: 2-bromo-1-phenylpyrrole；2-bromo-N-phenylpyrrole
• CAS: 30068-53-2
• 化学式: C₁₀H₈BrN
• 分子量: 222.084
• InChiKey: ZSLZXABWPGPWGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.5±13.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-bromo-1-phenyl-1H-pyrrole 在 正丁基锂 、 zinc chloride*2(tetrahydrofuran) 、 C₂₄H₅₄Cl₂P₂Pd₂⁽²⁺⁾ 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.5h， 以77%的产率得到1,1'-diphenyl-1H,1'H-[2,3']bipyrrolyl
  参考文献：
  名称：

  Molecular Wires using (Oligo)pyrroles as Connecting Units: An Electron Transfer Study

  摘要：

  A series of (oligo)pyrroles featuring redox-active terminal ferrocenyl groups (Fc(2)-((C4H2NPh)-C-c)(n) (4, n = 1; 9, n = 2; 16, n = 3; 20, n = 4)) has been prepared using a Negishi C,C cross-coupling reaction protocol. The bi-, ter-, and quaterpyrrole wire moieties have been built up by C,C cross-coupling reactions of trimethylsilyl-protected pyrrole units in the presence of [Pd(CH2C(CH3)2(P)((C4H9)-C-t)(2))(mu-Cl)](2) as precatalyst. The structural properties of the title compounds were investigated by spectroscopic means and single-crystal X-ray diffraction studies (9, 16, and 20). The influence of the increasing number of N-phenylpyrrole units on the electronic interaction between the iron centers was studied using electrochemistry (cyclic (CV) and square wave voltammetry (SWV)) as well as spectroelectrochemistry (in situ UV/vis/near-IR spectroscopy). With the exception of the diferrocenyl quaterpyrrole 20, the application of [(NBu4)-Bu-n][B(C6F5)(4)] as electrolyte allows the discrete oxidation of the ferrocenyl termini (Delta E degrees' = 450 mV (4), Delta E degrees' = 320 mV (9), Delta E degrees' = 165 mV (16)) in cyclic and square wave voltammograms. However, the iron centers of 20 were oxidized simultaneously, generating dicationic 20(2+). Additionally, one (9) or two (16 and 20) pyrrole-related well-defined reversible one-electron-redox processes were observed. The cyclic voltammetry data reveal that the splitting of the ferrocene-based redox couples, Delta E degrees', decreases with increasing oligopyrrole chain length and, hence, a greater metal-metal distance. The trends in Delta E degrees' with oligopyrrole structure also map to the electronic coupling between the ferrocene moieties, as estimated by spectroelectrochemical UV/vis/near-IR measurements. Despite the fact that there is no direct metal-metal interaction in diferrocenyl quaterpyrrole 20, a large absorption in the near-IR region is observed arising from photoinduced charge transfer from the oligopyrrole backbone to the redox-active ferrocenyl termini. These charge transfer absorptions have also been found in the dicationic oxidation state of the mono-(4), bi- (9), and terpyrroles (16). Within this series of diferrocenyl(oligo)pyrroles this CT band is shifted bathochromically with increasing chain length of the backbone motif.

  DOI：

  10.1021/om4007533
• 作为产物：
  描述：

  1-苯基吡咯 在 N-溴代丁二酰亚胺(NBS) 、 sodium sulfite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 2-bromo-1-phenyl-1H-pyrrole
  参考文献：
  名称：

  杂芳胺库：胺催化的烷氧基杂芳烃的铟催化亲核芳香取代

  摘要：

  在铟路易斯酸催化下，与/不与苯环稠合的富电子五元杂芳基亲电试剂与胺偶合生成具有广泛结构多样性的杂芳基胺。通过基于亲核芳香取代（S胺的亲核攻击，通过杂芳基- OME键的裂解的杂芳基形成前进Ñ AR）反应。与相应的传统S N Ar胺形成对比，目前基于S N Ar的杂芳基胺化反应无需依赖具有吸电子基团的杂芳基亲电子试剂和亲核性增强的金属酰胺。对NO 2，Br，I，CF 3等官能团的高度相容性观察到CN，CO 2 Et，吡啶基，噻唑基，C = C和OH基团，从而表明该方法的实用性和可靠性。机理研究表明，在此过程中，杂芳基环上可能会形成碳-铟键。

  DOI：

  10.1002/adsc.201701452

文献信息

• 1,2,3-Triazol-5-ylidene bearing a pyridine auxiliary based bidentate PEPPSI type palladium(II) complex: Synthesis, structure, and application in the direct arylation of pyridine N-oxide
  作者：Lin-Yu Jiao、Xiao-Mei Yin、Shanshan Liu、Ze Zhang、Ming Sun、Xiao-Xun Ma

  DOI：10.1016/j.catcom.2019.105889

  日期：2020.2

  A novel PEPPSI (pyridine enhanced precatalyst preparation stabilization and initiation) type palladium(II) complex has been synthesized and fully characterized by NMR, HR-MS, as well as elemental analysis. The molecular structure was finally confirmed by single crystal X-ray diffraction, and it revealed that the pyridyl-armed 1,2,3-triazole ligand is coordinated to the palladium in bidentate fashion

  合成了一种新型的PEPPSI（吡啶增强的前催化剂制剂的稳定和引发作用）型钯（II）配合物，并通过NMR，HR-MS和元素分析对其进行了全面表征。最终通过单晶X射线衍射确认了分子结构，并且揭示了吡啶基武装的1,2,3-三唑配体以二齿形式与钯配位。这种对空气和湿气不敏感的复合物已被证明是适合N-吡啶氧化物和2-溴吡咯芳基芳基化的合适催化剂，具有宽泛的官能团耐受性，证明了该复合物的坚固性和高效性。
• Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes
  作者：Indrajit Ghosh、Jagadish Khamrai、Aleksandr Savateev、Nikita Shlapakov、Markus Antonietti、Burkhard König

  DOI：10.1126/science.aaw3254

  日期：2019.7.26

  Two-for-one approach to photoredox In photoredox catalysis, an excited chromophore typically activates a single reactant either by oxidizing or reducing it. Ghosh et al. used a semiconductor catalyst to activate two reactants at once by quenching both an excited electron and the residual positive hole (see the Perspective by Swift). As such, two different reactive carbon or halide fragments could be

  光氧化还原二合一方法 在光氧化还原催化中，激发的发色团通常通过氧化或还原单个反应物来激活它。戈什等人。使用半导体催化剂通过淬灭激发的电子和残留的空穴来同时激活两种反应物（参见 Swift 的观点）。因此，可以将两个不同的反应性碳或卤化物片段附加到芳环上的不同位点。该催化剂还可以耐受氰化物等强亲核试剂，并且可以轻松回收和重复使用。科学，这个问题 p。360; 另见第。320 半导体光催化剂上氧化和还原位点的形成促进了双自由基加成反应。半导体表面上的光激发电子-空穴对可以与两种不同的基材进行氧化还原反应。与传统的电合成类似，主要的氧化还原中间体仅提供单独的氧化和还原产物，或者更罕见地结合成一种加成产物。在这里，我们报告了一种稳定的有机半导体材料，介孔石墨碳氮化物 (mpg-CN)，可以充当可见光光氧化还原催化剂，以协调氧化和还原界面电子转移到两个或三个组件中的两种不同基材。用于芳烃和杂芳烃的直接双重碳氢功能化的系统。mpg-CN
• 유기 전기 발광 소자용 발광 재료, 이를 이용한 유기 전기 발광 소자 및 유기 전기 발광 소자용 재료
  申请人：CHOI,DON-SOO 최돈수(419990450773)

  公开号：KR102201473B1

  公开（公告）日：2021-01-11

  발광 파장 조절 및 발광 효율이 우수한 퓨즈드 화합물, 그의 제조방법 및 상기 퓨즈드 화합물을 포함하는 유기전자소자를 제시한다.

  发光波长调节和发光效率优异的融合物化合物，其制备方法以及包含所述融合物化合物的有机电子器件。
• Duan, Xiao-Guang; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1997, # 18, p. 2695 - 2699
  作者：Duan, Xiao-Guang、Rees, Charles W.

  DOI：——

  日期：——
• Bromination and chlorination of pyrrole and some reactive 1-substituted pyrroles
  作者：H. M. Gilow、D. Edward Burton

  DOI：10.1021/jo00324a005

  日期：1981.5