2,3-bis(phenylethynyl)quinoxaline | 75163-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-bis(phenylethynyl)quinoxaline
• 英文别名: 2,3-bis(2-phenylethynyl)quinoxaline
• CAS: 75163-16-5
• 化学式: C₂₄H₁₄N₂
• 分子量: 330.389
• InChiKey: ODZUGJZBCAUACS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-bis(phenylethynyl)quinoxaline 在 硫酸 、 溶剂黄146 、 potassium bromide 作用下， 反应 1.0h， 以86%的产率得到2,3-bis((Z)-2-bromo-2-phenylvinyl)quinoxaline
  参考文献：
  名称：

  Electrophilic cyclizations of 2,3-dialkynylquinoxalines and 1,2-dialkynylbenzenes: a comparative study

  摘要：

  The reactivity of 2,3-dialkynylquinoxalines towards electrophiles (Br-2, I-2, ICI, NBS, HBr) has been studied. All tested reactions, except one with HBr, start with the addition of an electrophile to the carbon-carbon triple bond that promotes further 5-exo-dig carbocyclization ultimately yielding a mixture of stereoisomeric cyclopenta[b]quinoxaline derivatives. The nature of substituents on the C C bonds of the starting molecule influence the stereochemical result of the reaction. The ratio of isomeric cyclization products also depends on the electrophile used. ortho-Dialkynylbenzenes and ortho-dialkynylquinoxalines demonstrate rather similar reactivity towards halogen electrophiles, but differ in their reactions with hydrobromic acid, which is caused by the basic nature of the aza group of the quinoxaline substrate. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.098
• 作为产物：
  描述：

  苯丙炔醛缩二乙醛 以 甲苯 为溶剂， 反应 0.33h， 生成 2,3-bis(phenylethynyl)quinoxaline
  参考文献：
  名称：

  二炔基1,2-二酮的一步合成及其转化为带有烯二炔单元的稠合吡嗪

  摘要：

  描述了在CuBr和LiBr存在下由乙炔锂和草酰氯制备对称的末端保护的二炔基1,2-二酮3的简便方法。3与各种芳族和杂芳族1,2-二胺的缩合导致形成吡嗪基α-二炔基化杂环。二乙炔基喹喔啉的烯二炔亚结构可以在Bergman环化反应中进行热重排。

  DOI：

  10.1016/s0040-4020(97)01007-7

文献信息

• Regioselective 6-endo-dig iodocyclization: an accessible approach for iodo-benzo[a]phenazines
  作者：Sonu Kumar、Mohammad Mujahid、Akhilesh K. Verma

  DOI：10.1039/c7ob00671c

  日期：——

  A facile approach for the synthesis of substituted iodo-benzo[a]phenazines from 2-aryl-3-(aryl/alkylethynyl)quinoxalines via 6-endo-dig ring closure has been described under mild reaction conditions. Iodocyclization proceeds through the iodonium ion intermediate followed by nucleophilic cyclization with the C–H bond of the arene. Furthermore, the resulting 6-iodo-5-aryl/alkyl benzo[a]phenazine derivatives

  已经描述了在温和的反应条件下通过6-内挖开环从2-芳基-3-（芳基/烷基乙炔基）喹喔啉合成取代的碘代-苯并[ a ]吩嗪的简便方法。碘环化过程通过碘鎓离子中间体进行，然后通过芳烃的C–H键进行亲核环化。此外，所得的6-碘-5-芳基/烷基苯并[ a ]吩嗪衍生物允许通过采用各种偶联反应进行结构多样化。通过该化合物的X射线晶体学研究证实了碘-苯并[ a ]吩嗪的结构。
• Regioselective <i>5-endo-dig</i> Electrophilic Iodocyclization of Enediynes: A Convenient Route to Iodo-substituted Indenes and Cyclopenta-Fused Arenes
  作者：Rakesh K. Saunthwal、Abhinandan K. Danodia、Monika Patel、Sushil Kumar、Akhilesh K. Verma

  DOI：10.1002/asia.201601085

  日期：2016.11.7

  iodocyclization was selectively triggered by a distribution of electronic density along the alkyne bond. Subsequently, the iodo‐substituted indenes were diversified by employing palladium‐catalyzed cross‐coupling reactions and the coupled products were further confirmed by X‐ray crystallographic studies.

  一种有效的碘介导的区域选择性串联方法，用于从容易获得的烯炔中合成对称和不对称的碘取代的茚满和立体选择性的环戊达[ b ]吡啶/噻吩，该过程通过原位形成碘鎓中间体，然后进行区域选择性的5-内-已经描述了挖掘环化。分子内亲电碘环化是通过沿炔键的电子密度分布选择性触发的。随后，通过钯催化的交叉偶联反应使碘取代的茚满多样化，并通过X射线晶体学研究进一步证实了偶联产物。
• 1,3-Dipolar cycloaddition of azinium ylides to alkynyl hetarenes: a synthetic route to indolizine and pyrrolo[2,1-a]isoquinoline based heterobiaryls
  作者：Julia I. Nelina-Nemtseva、Anna V. Gulevskaya、Alexander F. Pozharskii、Huong T.L. Nguyen、Ekaterina A. Filatova

  DOI：10.1016/j.tet.2016.03.050

  日期：2016.5

  For the first time, π-deficient alkynyl hetarenes were used as dipolarophiles in a 1,3-dipolar cycloaddition reaction with in situ generated azinium ylides. A three-component reaction of pyridine or isoquinoline, ethyl chloroacetate and alkynyl hetarene (pyrazine, quinoxaline, uracil, or lumazine derivative) in the presence of a base gave the corresponding indolizine or pyrrolo[2,1-a]isoquinoline based

  第一次，在与原位生成的叠氮化物的1，3-偶极环加成反应中，将π缺乏的炔基戊烯用作亲极性。在碱存在下，吡啶或异喹啉，氯乙酸乙酯和炔基戊烯（吡嗪，喹喔啉，尿嘧啶或lumazine衍生物）的三组分反应得到相应的吲哚利嗪或吡咯并[2,1- a ]异喹啉基杂联芳基产量。反应以高区域选择性进行；在所有情况下，C中最缺乏电子的碳原子起始炔基戊烯的C键加到叠氮基内鎓盐的侧链碳上。炔基戊烯与叠氮化或其他1,3-偶极试剂的1,3-偶极环加成反应可以被视为杂联芳基的另一种合成方法。
• Pyrrolo[2,3-b]quinoxalines as inhibitors of firefly luciferase: Their Cu-mediated synthesis and evaluation as false positives in a reporter gene assay
  作者：Ali Nakhi、Md. Shafiqur Rahman、Ravada Kishore、Chandana Lakshmi T. Meda、Girdhar Singh Deora、Kishore V.L. Parsa、Manojit Pal

  DOI：10.1016/j.bmcl.2012.08.056

  日期：2012.10

  2-Substituted pyrrolo[2,3-b]quinoxalines having free NH were prepared directly from 3-alkynyl-2-chloroquinoxalines in a single pot by using readily available and inexpensive methane sulfonamide (or p-toluene sulfonamide) as an ammonia surrogate. The reaction proceeded in the presence of Cu(OAc)2 affording the desired product in moderate yield. The crystal structure analysis of a representative compound

  通过使用容易获得且便宜的甲烷磺酰胺（或对甲苯磺酰胺）作为氨代用品，在一个锅中直接由3-炔基-2-氯喹喔啉直接制备具有游离NH的2-取代的吡咯并[2,3- b ]喹喔啉。反应在Cu（OAc）2的存在下进行以中等收率得到所需产物。介绍了代表性化合物的晶体结构分析及其超分子相互作用。通过分子对接研究，这些化合物与荧光素酶的预测结合模式支持了某些合成的化合物对荧光素酶的抑制活性。由于荧光素酶的直接抑制作用，此处公开的主要观察结果可以提醒荧光素酶报道基因试验的用户可能的假阳性结果。
• N-Heterocycle-Fused Pentalenes by a Gold-Catalyzed Annulation of Diethynyl-Quinoxalines and -Phenazines
  作者：Kohei Sekine、Fabian Stuck、Jürgen Schulmeister、Thomas Wurm、Dominik Zetschok、Frank Rominger、Matthias Rudolph、A. Stephen K. Hashmi

  DOI：10.1002/chem.201803096

  日期：2018.8.27

  ed pentalenes and the study of their optoelectronic properties are described. The inhibition of the gold catalyst by the nitrogen centers in the substrate and the product could be overcome by increasing the reaction temperature to 130 °C, which usually leads to catalyst decomposition in gold catalysis. At 130 °C, 6,7‐di(arylethynyl)quinoxalines in chlorobenzene give the corresponding pentalenes. The

  描述了金催化的二乙炔N-杂环环化合成喹喔啉/吩嗪基戊二烯及其光电性能的研究。通过将反应温度提高到130°C，可以克服底物中氮中心对金催化剂的抑制作用，这通常会导致金催化反应中的催化剂分解。在130°C下，氯苯中的6,7-二（芳基乙炔基）喹喔啉可生成相应的戊烯。2，3-二（芳基乙炔基）喹喔啉的环化需要在微波辐射下更高的温度。与相应的萘基戊二烯相比，基于喹喔啉的戊二烯的LUMO含量较低。