3,6-二(吡啶-2-基)-2,5-二氢吡咯[3,4-C]吡咯-1,4-二酮 | 88949-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3,6-二(吡啶-2-基)-2,5-二氢吡咯[3,4-C]吡咯-1,4-二酮
• 英文名称: 2,5-dihydro-3,6-di-2-pyridylpyrrolo(3,4-c)pyrrole-1,4-dione
• 英文别名: 1,4-dipyridin-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 88949-26-2
• 化学式: C₁₆H₁₀N₄O₂
• 分子量: 290.281
• InChiKey: DDTUZVGCGRNBOY-UHFFFAOYSA-N

物化性质

• 沸点：
  719.9±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.98
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,6-二(吡啶-2-基)-2,5-二氢吡咯[3,4-C]吡咯-1,4-二酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以990 mg (91.4%)的产率得到3,6-Bis(2-pyridinyl)-2,5-dihydro-2,5-dimethylpyrrolo(3,4-c)pyrrole-1,4-dion
  参考文献：
  名称：

  3,6-bis-(2'-methoxyphenyl)-2,5-dihydro-2,5-dimethyl-pyrrolo

  摘要：

  III式的化合物是3,6-双-(2'-甲氧基苯基)-2,5-二氢-2,5-二甲基吡咯-(3,4-c)-吡咯-1,4-二酮。

  公开号：

  US05354869A1
• 作为产物：
  描述：

  2-氰基吡啶 、 丁二酸二丁酯 在 iron(III) chloride 、 2-甲基-2-丁醇 、 sodium 作用下， 以 2-甲基-2-丁醇 为溶剂， 反应 25.0h， 以60%的产率得到3,6-二(吡啶-2-基)-2,5-二氢吡咯[3,4-C]吡咯-1,4-二酮
  参考文献：
  名称：

  Optical properties of highly planar diketopyrrolopyrrole derivatives fixed by coordinate bonds

  摘要：

  Diketopyrrolopyrrole (DPP) derivatives bearing 2-pyridyl groups were synthesized, which could serve as anionic N,N'-chelate ligands consisting of two nitrogen atoms of the lactam moieties and the pyridyl groups. Coordination of the DPP ligand to boron and platinum yielded the corresponding DPP complexes. Their crystal structures exhibited coplanar structures between the DPP core and the 2-pyridyl groups, which indicated extended pi-conjugation. The maximum absorption wavelength of the DPP complexes was longer than that of the corresponding DPP ligands. The choice of the introduced element affects the optical properties of the DPP complexes; the platinum complex has a longer absorption wavelength than the boron complex. The theoretical calculation revealed that these absorptions can be attributed to the pi-pi* transition. The introduction of the coordinating elements predominantly lowers the band gap. In addition, the substituent on the 2-pyridyl group can also modulate the energy levels. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.090

文献信息

• Template‐Free Self‐Assembly of Molecular Trefoil Knots and Double Trefoil Knots Featuring Cp*Rh Building Blocks
  作者：Wei‐Long Shan、Xiang Gao、Yue‐Jian Lin、Guo‐Xin Jin

  DOI：10.1002/chem.202000525

  日期：2020.4.16

  hexanuclear trefoil knots featuring Cp*Rh building blocks by the template-free self-assembly of four different rigid and flexible ligands. Transformations between the trefoil knots and the corresponding macrocycles can be induced using concentration effects. Remarkably, the hexanuclear trefoil knot 5 was shown to assemble further, providing rare examples of [12+1] heteronuclear double trefoil knots ( 5a/5b/5c/5d

  理解和控制自组装结构的拓扑在超分子化学中起着基本作用。在这里，我们描述了通过四个不同的刚性和柔性配体的无模板自组装来制备一系列具有Cp * Rh构建基块的四核金属矩形和六核三叶结。三叶结与相应的大环之间的转化可以利用集中效应来诱导。值得注意的是，六核三叶结5进一步组装，通过酰胺氧原子与次要金属离子Na + / K +的配位提供了[12 + 1]异核双三叶结（5a / 5b / 5c / 5d）的罕见例子。 / Ca2 + / Cd2 +。合成结果得到单晶X射线衍射分析的支持。
• Straightforward <i>N</i>-alkylation of diketopyrrolopyrroles through the Mitsunobu reaction with benzyl, α-branched, and chiral alcohols
  作者：Maurizio Mastropasqua Talamo、Flavia Pop、Narcis Avarvari

  DOI：10.1039/d1cc02472h

  日期：——

  diketopyrrolopyrroles (DPPs) represents a fundamental step to ensure solubility and further processability. Commonly used nucleophilic substitution in halogenated derivatives is replaced in this work by the Mitsunobu reaction affording unprecedented DPPs with α-branched and chiral chains.

  二酮吡咯并吡咯 (DPP)的N-烷基化代表了确保溶解性和进一步加工性的基本步骤。在这项工作中，卤化衍生物中常用的亲核取代被 Mitsunobu 反应取代，提供了前所未有的具有 α 支链和手性链的 DPP。
• Host–Guest Feature of DPPP Bridged Arene–Ruthenium Clip Derived Molecular Rectangle
  作者：Suman Dhara、Mohd. Asif Ansari、Goutam Kumar Lahiri

  DOI：10.1021/acs.inorgchem.9b01468

  日期：2019.8.19

  encapsulation of two pyrene molecules inside the hydrophobic cavity of 5, due to the twisted 4,4′-bipyridine spacer units between the two ruthenium clips. It also attributed a noncovalent CH−π interaction involving protons of pyrene and the π-electron cloud of 4,4′-bipyridine as well as a weak interaction between pyrene protons and the pendant C═O group of DPPP. Encapsulation of the guest molecule (pyrene) inside

  DPPP 2–（H 2 DPPP = 2,5-二氢-3,6-二-2-吡啶基吡咯并（3,4- c）吡咯-1,4-二酮）的发展（NN∩NN）桥接的钌络合物[ （Cym）（X）Ru II（μ-DPPP）Ru II（X）（Cym）]（Cym =对-cymene，X = OTf –（1），SCN –（2），N 3 –（3）， NO 2 –（4））被认为是构成金属矩形的可能的分子夹子。2 – 4的晶体结构分别针对单齿SCN –，N 3 –和NO 2 –基团建立了抗构型。虽然分子片段2 - 4失败以提供所需的metallarectangle结合所述4,4'-联吡啶间隔，1与不稳定的光学传递函数组提供便利，以便实现metallarectangle 5。5的晶体结构表明，两个扭曲的4,4'-联吡啶间隔基以对称方式桥接在二聚体1的两个单元之间，这实际上导致了更新的一类分子矩形5具有8.32×11.11埃阳离子
• Metal–Metal Bridging Using the DPPP Dye System: Electronic Configurations within Multiple Redox Series
  作者：Arijit Singha Hazari、Abhishek Mandal、Katharina Beyer、Alexa Paretzki、Wolfgang Kaim、Goutam Kumar Lahiri

  DOI：10.1021/acs.inorgchem.6b03112

  日期：2017.3.6

  corresponding precursors, isolated as rac diastereomers. Oxidation was observed to occur mainly at the bridging ligand (DPPP2– → DPPP•–), whereas the site of reduction (DPPP, Ru, or L) depends on effects from the ancillary ligands L. The metal coordination of a derivative of the pigment forming 2,5-dihydro-pyrrolo(3,4-c)pyrrole-1,4-dione (DPP) dyes and the analysis of corresponding multistep redox series add to

  氧化还原系列[L n Ru（μ-DPPP）RuL n ] k，H 2 DPPP = 2,5-二氢-3,6-二-2-吡啶基吡咯并（3,4- c）吡咯-1,4-二酮和通过伏安法（CV，DPV），EPR和UV-vis-NIR光谱电化学法研究了L = 2,4-戊二酮（aCAC –），2,2'-联吡啶（bpy）和2-苯基偶氮吡啶（pap） ，由TD-DFT计算支持。晶体结构分析和1 1 H NMR表明氧化态[（ACAC）2的Ru III（μ-DPPP 2- ）的Ru III（ACAC）2 ]和[（联吡啶）2的Ru II（μ-DPPP 2- ）的RuII（bpy）2 ] 2+为相应的前体，被分离为rac非对映体。观察到氧化主要发生在桥连配体（DPPP 2 →DPPP •）上，而还原位点（DPPP，Ru或L）取决于辅助配体L的作用。形成2,5-二氢-吡咯并（3,4- c）吡咯-1,4-二酮（DPP）染料
• Same knot, longer rope: altering ligand geometry provides control over nuclearity in self-assembled trefoil knots
  作者：Qi-Li-Sha Wang、Yue-Jian Lin、Guo-Xin Jin

  DOI：10.1039/d1cc03699h

  日期：——

  Selective constructions of Cp*Rh(iii)-based hexanuclear and octanuclear trefoil knots are realized using two ester bipyridyl ligands bearing minor differences in geometry.

  利用两种几何上略有不同的酯基联吡啶配体，实现了选择性构建Cp*Rh(iii)基六核和八核三叶草结构。