2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole | 476004-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole
• 英文别名: 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole
• CAS: 476004-84-9
• 化学式: C₁₆H₂₇B₂NO₄
• 分子量: 319.017
• InChiKey: IKJJYRIQKAWRDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P501,P270,P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313,P301+P312+P330
• 危险性描述：
  H302,H315,H319

反应信息

• 作为反应物：
  描述：

  1-溴-3-碘苯 、 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以60%的产率得到2,5-di(3-bromophenyl)pyrrole
  参考文献：
  名称：

  Synthesis, Structure, and Optical Properties of Di-m-benzihexaphyrins (1.1.0.0.0.0) and Di-m-benziheptaphyrins (1.0.1.0.0.0.0): Blackening of m-Phenylene-Linked Dicarbaporphyrinoids by Simple π-Expansion

  摘要：

  Acid-catalyzed condensation of a newly prepared di-m-benzipentapyrrane with appropriate mono- and diheterocyclic dialcohols selectively produced stable di-m-benzihexaphyrins and di-m-benziheptaphyrins with only two meso-carbon bridges. Single-crystal X-ray diffraction analyses reveal planar conformation with slight distortion of bridged phenylene rings. Despite the presence of m-phenylene units interrupting the global delocalization, the presence of bithiophene units in di-m-benziheptaphyrins 3a-b exhibits altered optical features covering the entire visible region (ca. 250-720 nm), exhibiting a black dye property as a "metal-free" porphyrinoid.

  DOI：

  10.1021/acs.joc.0c00754
• 作为产物：
  描述：

  吡咯 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以75%的产率得到2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole
  参考文献：
  名称：

  双（频哪醇）二硼在铱催化的五元杂芳烃上的直接硼化反应：区域选择性，化学计量和室温反应

  摘要：

  由1/2 [Ir（OMe）（COD）] 2和4,4'-二叔丁基-2,2'-联吡啶生成的铱（I）络合物催化2-取代的噻吩，呋喃的直接硼化反应在室温下，相对于己烷中双（频哪醇）二硼的化学计量的吡咯和吡咯。高产率地形成了由5-位区域选择性CH活化引起的杂芳基硼酸酯。用等摩尔量的二硼区域选择性地提供未取代的杂芳烃的类似硼烷基化，选择性地提供了2，5-双（硼基）杂芳烃。

  DOI：

  10.1002/adsc.200303058

文献信息

• Noncovalent Interactions in Ir-Catalyzed C–H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters
  作者：Md Emdadul Hoque、Ranjana Bisht、Chabush Haldar、Buddhadeb Chattopadhyay

  DOI：10.1021/jacs.7b04490

  日期：2017.6.14

  An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented

  描述了一种用于芳族酯的对位选择性硼化的有效策略。为了获得高的对位选择性，已经开发了一种新的催化体系，该体系改变了联吡啶的核心结构。有人提出，L型配体对于通过非共价相互作用识别酯羰基的氧原子的功能至关重要，这为超选择性C–H活化/硼化提供了空前的控制因素。
• [EN] NITROGEN-CONTAINING AROMATIC COMPOUNDS AND METAL COMPLEXES<br/>[FR] COMPOSÉS AROMATIQUES COMPRENANT DE L'AZOTE ET COMPLEXES MÉTALLIQUES
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2011052805A1

  公开（公告）日：2011-05-05

  To provide nitrogen-containing aromatic compounds with excellent oxygen reduction activity, metal complexes containing them, and catalysts and electrodes employing the same, the present invention provides an aromatic compound satisfying the following conditions (a) and (b): (a) It has 2 or more structures surrounded by at least 4 coordinatable nitrogen atoms (which structures may be the same or different), (b) At least one of the nitrogen atoms composing the structure is a nitrogen atom in a 6-membered nitrogen-containing heterocyclic ring.

  为了提供具有优异氧还原活性的含氮芳香化合物，含有它们的金属配合物，以及使用相同金属配合物的催化剂和电极，本发明提供了满足以下条件（a）和（b）的芳香化合物：（a）它具有至少4个可配位氮原子包围的2个或更多结构（这些结构可以相同也可以不同），（b）构成结构的氮原子中至少有一个是6元氮含杂环的氮原子。
• Iridium-catalyzed C–H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: regioselective synthesis of heteroarylboronates
  作者：Jun Takagi、Kazuaki Sato、John F Hartwig、Tatsuo Ishiyama、Norio Miyaura

  DOI：10.1016/s0040-4039(02)01135-8

  日期：2002.8

  The C–H coupling of aromatic heterocycles with bis(pinacolato)diboron was carried out in octane at 80–100°C in the presence of a 1/2[IrCl(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) catalyst (3 mol%). The reactions of five-membered substrates such as thiophene, furan, pyrrole, and their benzo-fused derivatives exclusively produced 2-borylated products, whereas those of six-membered heterocycles including

  芳香族杂环与双（频哪醇）二硼烷的C–H偶联是在80–100°C的辛烷中，在存在1/2 [IrCl（COD）] 2-（4,4'-二酯的条件下进行的-2，2'-联吡啶-丁基）催化剂（3mol％）。五元底物（例如噻吩，呋喃，吡咯及其苯并稠合衍生物）的反应仅生成2硼化产物，而六元杂环（包括吡啶和喹啉）的反应则选择性地在3位发生。还通过使用几乎等摩尔量的底物和二硼来实现双（硼基）杂芳族化合物的区域选择性合成。
• meso-to-meso 2,5-Pyrrolylene bridged zig-zag porphyrin arrays
  作者：Senmiao Zhang、Jun Oh Kim、Yajie Li、Bin Wen Bin Wen、Mingbo Zhou、Shubin Liu、Naoki Aratani、Ling Xu、Dongho Kim、Jianxin Song

  DOI：10.1039/c7cc06793c

  日期：——

  5-Pyrrolylene bridged zig-zag porphyrin arrays have been synthesized via a stepwise Suzuki–Miyaura cross coupling reaction. Both the dimeric and trimeric structures of ZnII porphyrin were confirmed by X-ray diffraction analysis. DFT calculations indicate that the porphyrin oligomers are all in zig-zag conformations. The UV/Vis absorption and emission spectra of these porphyrin oligomers were red-shifted

  内消旋-到-内消旋2,5-吡咯亚基桥接Z字形卟啉阵列已经合成通过逐步Suzuki-Miyaura交叉偶联反应。X射线衍射分析证实了Zn II卟啉的二聚体和三聚体结构。DFT计算表明，卟啉低聚物均呈之字形。这些卟啉低聚物的紫外/可见光吸收和发射光谱随着其卟啉单元数目的增加而红移。
• Synthesis and Self-Assembly of Macrocyclic Mesogens Based on 1,10-Phenanthroline
  作者：Hassan Norouzi-Arasi、Wojciech Pisula、Alexey Mavrinskiy、Xinliang Feng、Klaus Müllen

  DOI：10.1002/asia.201000642

  日期：2011.2.1

  Mesogenie in a bottle: The first liquid‐crystalline 1,10‐phenanthroline‐based macrocycles were synthesized by Suzuki–Miyaura cross‐coupling. Their optical properties and mesomorphism were investigated by UV/Vis absorption and emission spectroscopy, DSC, and 2D WAXS measurements. These studies revealed formation of columnar superstructures.

  瓶中的介晶：Suzuki-Miyaura交叉偶联合成了第一个基于液晶的1,10-菲咯啉的大环化合物。通过紫外/可见吸收和发射光谱，DSC和2D WAXS测量研究了它们的光学性质和同晶型。这些研究揭示了柱状上部结构的形成。