4-((4-ethynylphenyl)ethynyl)benzonitrile | 189099-74-9

• 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: 4-((4-ethynylphenyl)ethynyl)benzonitrile
• 英文别名: 4-(4-Ethynylphenylethynyl)benzonitrile；4-(4-Ethynyl-phenylethynyl)-benzonitrile；4-[2-(4-ethynylphenyl)ethynyl]benzonitrile
• CAS: 189099-74-9
• 化学式: C₁₇H₉N
• 分子量: 227.265
• InChiKey: FBIPTKVQICZRMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±27.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4-二碘-2,5-二(辛基氧基)苯 、 4-((4-ethynylphenyl)ethynyl)benzonitrile 在 palladium dichloride copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以78%的产率得到4,4'-(4,4'-(2,5-bis(octyloxy)-1,4-phenylene)bis(ethyne-2,1-diyl)bis(4,1-phenylene))bis(ethyne-2,1-diyl)dibenzonitrile
  参考文献：
  名称：

  Efficient synthesis of thioamide terminated molecular wires

  摘要：

  Bis-thioamide terminated 'molecular wires' are formed in a high yield under mild conditions from readily synthesised bisnitrile terminated molecules and aqueous ammonium sulfide in DMF. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.032
• 作为产物：
  描述：

  (4-碘苯基乙炔)三甲基硅烷 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醇 、 二乙胺 为溶剂， 反应 20.5h， 生成 4-((4-ethynylphenyl)ethynyl)benzonitrile
  参考文献：
  名称：

  Selective and efficient access to ortho, meta and para ring-substituted phenylacetylene derivatives R-[CC-C6H4]x-Y (Y : H, NO2, CN, I, NH2)

  摘要：

  ortho, meta and para isomers of iodo and amino ring-substituted phenylacetylene as well as rod-like arylacetylene derivatives were prepared by a simple synthetic route involving three consecutive reactions: the palladium-catalysed carbon-carbon bond formation, the Sandmeyer reaction and thr desilylation of die protected trimethylsilylalkynes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00451-1

文献信息

• Synthesis and non-linear properties of disubstituted diphenylacetylene and related compounds
  作者：Koichi Kondo、Takumi Fujitani、Noriaki Ohnishi

  DOI：10.1039/a606915k

  日期：——

  A variety of disubstituted diphenylacetylenes and related compounds have been synthesized by a modified Horner–Emmons reaction, and their second harmonic generation (SHG) has been evaluated by the Kurtz powder method. The diphenylacetylenes with weak electron-donating and -withdrawing groups are found to be efficient for SHG, as well as having the lowest cut-off wavelength.

  通过改进的Horner-Emmons反应合成了多种二取代二苯乙炔及相关化合物，并通过Kurtz粉末法评估了它们的二次谐波发生（SHG）性能。研究发现，具有弱供电子和吸电子基团的二苯乙炔在SHG方面效率较高，同时具有最低截止波长。
• Crystal engineering using very short and linear C(sp)–H⋯N hydrogen bonds: formation of head-to-tail straight tapes and their assembly into nonlinear optical polar crystals
  作者：Masakazu Ohkita、Takanori Suzuki、Takashi Tsuji、Keitaro Nakatani

  DOI：10.1039/b103689k

  日期：——

  The crystallization of 4-ethynylpyridine (1) and 4-(4-ethynylphenyl)ethynylpyridine (2) leads to C(sp)-H⋯N hydrogen bonded straight tapes that further assemble into polar crystals, in the case of 2, and show intense powder SHG response, 8 times more efficient than crystalline urea.

  4-乙炔基吡啶（1）和4-(4-乙炔基苯基)乙炔基吡啶（2）的结晶导致C(sp)-H···N氢键连接的直线链，这些链进一步组装成极性晶体，在2的情况下，并且显示出强烈的粉末二次谐波生成（SHG）响应，其效率是结晶尿素的8倍。
• Variable Pore Size, Variable Chemical Functionality, and an Example of Reactivity within Porous Phenylacetylene Silver Salts
  作者：Y.-H. Kiang、Geoffrey B. Gardner、Stephen Lee、Zhengtao Xu、Emil B. Lobkovsky

  DOI：10.1021/ja991100b

  日期：1999.9.1

  Investigations on molecular variants of the 3-fold symmetric 1,3,5-tris(4-ethynylbenzonitrile)benzene crystallized with silver triflate revealed a nearly invariant pseudohexagonal porous structure type. Modifications involved the attachment of pendant groups to the central aromatic ring of the parent molecule. Pendant groups include the vinyl group, stilbene, the chiral group myrtanol, and groups with different chemical functionalities such as alcohols, ethers, and esters. Modifications also included the addition of elongated spacer units between the central benzene ring and the peripheral nitrile groups. In these molecules the acetylene bridges of 1,3,5-tris(4-ethynylbenzonitrile)benzene were replaced with diacetylene, ethynylbenzene, and diethynylbenzene type units. Single-crystal refinements for pentoxy-2,4,6-tris(4-ethynylbenzonitril)benzene.AgOTf and 1,3,5-tris(4-(4-ethynylbenzonitrile)phenyl)benzene.AgOTf as well as powder data on 12 crystalline phases showed the consistent formation of pseudohexagonal channels, demonstrating that the parent porous architecture is stable both to functional modification of the interior of the channel as well as to enlargement of the pores. Pentoxy-2,4,6-tris(4-ethynylbenzonitrile)benzene.AgOTf refined in the monoclinic space group Am. 1,3,5-Tris(4-(4-ethynylbenzonitrile)phenyl)benzene.AgOTf was found to be triclinic with space group P (1) over bar. These crystals have pseudohexagonal channels respectively 15 and 25 Angstrom in diameter. Cell constants based on powder data are compatible with channel diameters ranging from 10 to 30 Angstrom. The latter channel diameters are among the largest known for organic porous solids. The introduction of the chiral myrtanol unit led to the preparation of a chiral porous solid. The thermal and chemical stabilities of these phases were investigated. The pseudohexagonal structure proved stable to complete solvent loss from the channel. It was found in the case of a host with alcohol functionality that an acid anhydride guest, trifluoroacetic anhydride, reacted with the host to form an ester with retention of the porous structure type.