2,6-di(1H-indol-2-yl)pyridine | 3882-41-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,6-di(1H-indol-2-yl)pyridine
• 英文别名: 2-[6-(1H-indol-2-yl)pyridin-2-yl]-1H-indole
• CAS: 3882-41-5
• 化学式: C₂₁H₁₅N₃
• 分子量: 309.37
• InChiKey: GBEAAMPTUUDRIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6-di(1H-indol-2-yl)pyridine 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 [Pt(BIP)Py]
  参考文献：
  名称：

  Liu, Qinde; Thorne, Lisa; Kozin, Igor, Journal of the Chemical Society Dalton Transactions, 2002, # 16, p. 3234 - 3240

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二乙酰基吡啶 在 PPA 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2,6-di(1H-indol-2-yl)pyridine
  参考文献：
  名称：

  Polyaza-cavity shaped molecules. 14. Annelated 2-(2'-pyridyl)indoles, 2,2'-biindoles, and related systems

  摘要：

  DOI：

  10.1021/jo00268a040

文献信息

• Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates
  作者：Manar Ahmed Fouad、Francesco Ferretti、Dario Formenti、Fabio Milani、Fabio Ragaini

  DOI：10.1002/ejoc.202100789

  日期：2021.9.14

  A very efficient, general and scalable protocol for the preparation of indoles and other N-heterocycles from suitably substituted nitroarenes using alkyl and phenyl formates as CO surrogates was described. Using phenyl formate, the products were isolated in yields often higher than those previously achieved by using gaseous CO. The mechanism of both the decarbonylation reaction of phenyl formate and

  描述了使用烷基和苯基甲酸酯作为 CO 替代物从适当取代的硝基芳烃制备吲哚和其他N-杂环的非常有效、通用和可扩展的方案。使用甲酸苯酯，产物的分离产率通常高于以前使用气态 CO 实现的产率。通过动力学和机理研究阐明了甲酸苯酯的脱羰反应和环化反应的机理。
• Synthesis of N-Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates
  作者：Dario Formenti、Francesco Ferretti、Fabio Ragaini

  DOI：10.1002/cctc.201701214

  日期：2018.1.9

  A series of alkyl and aryl formate esters were evaluated as CO sources in the Pd‐ and Pd/Ru‐catalyzed reductive cyclization of substituted nitro compounds to afford heterocycles, especially indoles. Phenyl formate was found to be the most effective, and it allowed the desired products to be obtained in excellent yields, often higher than those previously reported with pressurized CO. Through detailed

  在Pd和Pd / Ru催化的取代硝基化合物的还原环化反应中，评估了一系列甲酸烷基酯和芳基酯作为CO的来源，以提供杂环，尤其是吲哚。人们发现甲酸苯甲酸是最有效的，它可以以优异的收率获得所需的产物，通常比以前用加压CO报道的要高。通过详细的实验和动力学研究，我们能够区分金属催化的碱介导的甲酸苯酯的活化，并证实仅碱可有效催化其脱羰基作用。
• Deprotection of <i>N</i> ‐ <i>tert</i> ‐Butoxycarbonyl (Boc) Protected Functionalized Heteroarenes via Addition–Elimination with 3‐Methoxypropylamine
  作者：Zachary Z. Gulledge、Jesse D. Carrick

  DOI：10.1002/ejoc.201901811

  日期：2020.3.31

  The utilization of 3‐methoxypropylamine as a mild deprotecting agent for various N‐Boc protected heteroarenes via a proposed addition/elimination mechanism is described. Method development, application to various heteroarenes including indoles, 1,2‐indazoles, 1,2‐pyrazoles, and related derivatives, a ten‐fold scale‐up reaction, and experimental evaluation of a preliminary mechanistic hypothesis are

  描述了通过建议的添加/消除机理将3-甲氧基丙胺用作各种N- Boc保护的杂芳烃的温和脱保护剂。本文报道了方法开发，对各种杂芳烃的应用，包括吲哚，1,2-吲唑，1,2-吡唑和相关衍生物，十倍放大反应以及初步机理假设的实验评估。
• Formic Acid as Carbon Monoxide Source in the Palladium-Catalyzed N-Heterocyclization of <i>o</i>-Nitrostyrenes to Indoles
  作者：Manar Ahmed Fouad、Francesco Ferretti、Fabio Ragaini

  DOI：10.1021/acs.joc.2c02613

  日期：——

  generation of CO from nontoxic and affordable sources. Among several CO sources that have been previously explored for the generation of gaseous CO, here we report the use of cheap and readily available formic acid as an effective reductant for the reductive cyclization of o-nitrostyrenes. The reaction is air and water tolerant and provides the desired indoles in yields up to 99%, at a low catalyst loading

  使用 CO 作为廉价还原剂，研究了邻硝基苯乙烯生成吲哚的还原环化反应已有 30 年，但它仍然是一个有趣的研究和改进领域。然而，使用有毒的 CO 气体有几个缺点。因此，非常优选使用安全有效的替代品从无毒且负担得起的来源原位生成 CO。在先前探索用于产生气态 CO 的几种 CO 来源中，我们在此报告使用廉价且容易获得的甲酸作为有效还原剂，用于还原环化o-硝基苯乙烯。该反应具有空气和水耐受性，并以高达 99% 的收率提供所需的吲哚，催化剂负载量较低 (0.5 mol%)，并且不会产生有毒或难以分离的副产物。可以使用便宜的玻璃厚壁“压力管”代替较少可用的高压灭菌器，即使在 2 g 的规模上，从而扩大了我们协议的适用性。
• Novel Phosphorescent Cyclometalated Organotin(IV) and Organolead(IV) Complexes of 2,6-Bis(2‘-indolyl)pyridine and 2,6-Bis[2‘-(7-azaindolyl)]pyridine
  作者：Wen-Li Jia、Qin-De Liu、Ruiyao Wang、Suning Wang

  DOI：10.1021/om030404a

  日期：2003.9.1

  Four novel five-coordinated Sn(IV) and Pb(IV) complexes of 2,6-bis(2'-indolyl)pyridine (H(2)bip) and 2,6-bis[2'-(7-azaindolyl)lpyridine (H(2)bap) were synthesized. These four complexes have the formulas Sn(bip)Ph-2 (1), Sn(bap)Ph-2 (2), Pb(bip)Ph-2 (3), and Pb(bap)Ph-2 (4), respectively. The structures were determined by single-crystal X-ray diffraction. In the complexes, the metal centers are tridentately chelated by the bip or the bap ligand and further coordinated by two phenyl groups, resulting in a distorted-trigonal-bipyramidal geometry. These complexes display interesting extended pi-pi stack structures in the solid state. Complexes 1 and 2 are luminescent at room temperature in solution and the solid state. At 77 K in THF solution, all four complexes display both blue-green fluorescent and orange-red phosphorescent emissions, which originate from ligand-centered pi-->pi* transitions. The Sn(IV) and Pb(IV) centers play a key role in enhancing phosphorescent emission of the bip and bap ligands.