1,2-bis(iodoethynyl)benzene | 20799-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2-bis(iodoethynyl)benzene
• 英文别名: 1,2-Bis(2-iodoethynyl)benzene
• CAS: 20799-74-0
• 化学式: C₁₀H₄I₂
• 分子量: 377.951
• InChiKey: YBABULFSXPPWHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2-bis(iodoethynyl)benzene 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 144.0h， 生成
  参考文献：
  名称：

  用于阴离子识别的新型卤素键合 1,2-碘-三唑鎓-三唑苯基序

  摘要：

  报道了一系列基于新型 1,2-碘-三唑鎓-三唑苯基序的卤素键 (XB) 无环阴离子受体的合成。一维和二维1 H 和19 F NMR 光谱技术的组合阐明了与加入基于邻位取代的碘三唑的 XB 供体相关的关键构象效应。1H NMR 阴离子滴定实验突出了单阳离子 XB 碘-三唑鎓-三唑苯受体的阴离子识别效力，与双阳离子氢键 (HB) 双原三唑鎓受体类似物相比，显着形成更强的卤化物复合物。X 射线晶体结构分析提供了对卤化物结合诱导的构象变化和配位模式的见解，揭示了与多齿 XB 供体阵列相关的独特电子和空间结果。

  DOI：

  10.1016/j.poly.2021.115482
• 作为产物：
  描述：

  1,2-二碘苯 在 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 silver fluoride 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 生成 1,2-bis(iodoethynyl)benzene
  参考文献：
  名称：

  Fusing Triazoles: Toward Extending Aromaticity

  摘要：

  A novel method to extend aromaticity by one benzene and two triazole rings was developed and optimized. This two-step route employs the copper-catalyzed azide-haloalkyne cycloaddition reaction of an ortho-bis(iodoacetylene) system and the subsequent intramolecular homocoupling fusion of the neighboring iodotriazoles, a process in which an additional benzene ring is formed. This versatile methodology allows one to extend the core size of chromophores and, consequently, to tune the material's properties.

  DOI：

  10.1021/ol201290q

文献信息

• Infinite and discrete halogen bonded assemblies based upon 1,2-bis(iodoethynyl)benzene
  作者：Eric Bosch、Samantha J. Kruse、Ryan H. Groeneman

  DOI：10.1039/c8ce01984c

  日期：——

  Infinite and discrete co-crystals based upon 1,2-bis(iodoethynyl)benzene as a halogen bond donor to either a symmetrical bipyridine or an unsymmetrical monopyridine-based acceptor is reported.

  报告中介绍了以 1,2-双（碘乙炔基）苯为卤素键供体，以对称双吡啶或不对称单吡啶为受体的无限离散共晶体。
• The trisubstituted-triazole approach to extended functional naphthalocyanines
  作者：Michal Juríček、Kathleen Stout、Paul H.J. Kouwer、Alan E. Rowan

  DOI：10.1142/s1088424611003781

  日期：2011.9

  Recently, a novel modular approach to octatriazole-derived phthalocyanines (Pcs; 1) was developed and optimized in our group; herein, the pool of the functional Pc materials was expanded for an additional candidate (2), a fused derivative of 1. Compared with 1, the aromaticity in 2 is extended by an additional four benzene and eight triazole rings and, in addition, the triazole units and the Pc core co-create four functional, in-plane cavities. Various methods to link the unsubstituted carbon atoms of the neighboring triazoles in 1 to afford atomically flat naphthalocyanine (Nc) analogs (2), containing eight fused triazole moieties, were studied. Several synthetic routes were designed, among them the trisubstituted-triazole approach, which was found to be the most suitable route. The crucial steps of this approach, the copper-catalyzed azide-haloalkyne cycloaddition and the intramolecular homocoupling reactions, were first studied on a model system; subsequently, this methodology was applied in the synthesis of the desired Nc 2. The increased core size and the π-electron deficient structure predict this class of Ncs to possess very strong aggregation properties. Moreover, owing to the presence of four tridentate half-cavities, the final properties of the molecule or the assembly can, in principle, be further tuned by doping with metals or guest molecules.

  与 1 相比，2 的芳香度增加了四个苯环和八个三唑环，此外，三唑单元和酞菁核共同创造了四个功能性平面空腔。研究人员研究了各种方法，将 1 中相邻三唑的未取代碳原子连接起来，从而得到含有八个融合三唑分子的原子平坦的萘酞菁（Nc）类似物（2）。研究人员设计了几种合成路线，其中三取代三唑法被认为是最合适的路线。首先在一个模型体系上研究了这种方法的关键步骤，即铜催化的叠氮-卤代烃环加成反应和分子内均偶联反应；随后，将这种方法应用于合成所需的 Nc 2。增大的核心尺寸和π-电子缺陷结构预示着这类 Ncs 具有非常强的聚集特性。此外，由于存在四个三叉半腔，原则上可以通过掺杂金属或客体分子来进一步调整分子或组装体的最终特性。
• Strong and Selective Halide Anion Binding by Neutral Halogen-Bonding [2]Rotaxanes in Wet Organic Solvents
  作者：Jason Y. C. Lim、Thanthapatra Bunchuay、Paul D. Beer

  DOI：10.1002/chem.201700030

  日期：2017.4.3

  organic solvent mixtures. Importantly, halide‐binding strength and selectivity can be modulated by varying the number and position of the halogen bond donor iodotriazole groups within the interlocked cavity; the rotaxane containing the largest number of halogen bond donor groups exhibits the highest halide anion‐binding affinities. By varying the percentage of water content in the solvent, neutral

  用于阴离子识别的中性互锁主体分子的设计和构建很少见。使用活性金属模板方法，可以制备包含两个，三个和四个碘代三唑基团的中性卤素键合（XB）轮烷族，这些环氧基团被集成到大环和轴组件中。尽管互锁的主体是中性的，但这种轮烷体系仍能够在湿有机溶剂混合物中牢固而有选择地结合卤化物阴离子。重要的是，可以通过改变互锁腔内卤素键供体碘三唑基团的数量和位置来调节卤化物的结合强度和选择性。含有最多卤素键供体基团的轮烷具有最高的卤化物阴离子结合亲和力。通过改变溶剂中水的百分比，
• A novel photochemical cyclisation of o-bisiodoethynylbenzene to substituted naphthalenes
  作者：I. D. Cambell、G. Eglinton

  DOI：10.1039/j39680002120

  日期：——

  Irradiation of a thin liquid-film of o-bisiodoethynylbenzene (I) produces insoluble material, and, in addition, a small amount of a tetraiodonaphthalene. Irradiation of a benzene solution of (I) produces o-bisphenylethynyl benzene (II), and small quantities of a number of substituted naphthalenes.

  辐照邻-双碘乙炔基苯（I）的液体薄膜会产生不溶物，此外还会产生少量的四碘代萘。辐射（I）的苯溶液产生邻-双苯基乙炔基苯（II）和少量的许多取代的萘​​。
• Gold-Catalyzed Hydroarylating Cyclization of 1,2-Bis(2-iodoethynyl)benzenes
  作者：Pascal Nösel、Vanessa Müller、Steffen Mader、Setareh Moghimi、Matthias Rudolph、Ingo Braun、Frank Rominger、A. Stephen K. Hashmi

  DOI：10.1002/adsc.201400749

  日期：2015.2.9

  Abstract1,5‐Diynes bearing halogen‐substituted alkynes were synthesized and converted in the presence of a gold catalyst. In contrast to the corresponding hydroarylating aromatization reaction with terminal alkynes, a totally different reaction mode was observed. Instead of the expected dual catalysis pathway, only one gold center is needed and a 1,2‐halogen migration is initiated in which either a gold vinylidene species or a gold carbenoid is involved. By the incorporation of one solvent molecule, diiodinated aromatic products are obtained in high selectivity.magnified image