1,2-双(2-噻唑基)乙炔 | 666825-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1,2-双(2-噻唑基)乙炔
• 英文名称: 1,2-bis(2-thiazolyl)ethyne
• 英文别名: 2-[2-(1,3-Thiazol-2-yl)ethynyl]-1,3-thiazole
• CAS: 666825-29-2
• 化学式: C₈H₄N₂S₂
• 分子量: 192.265
• InChiKey: YWSUSFJTKZPJAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-双(2-噻唑基)乙炔 在 dicobalt octacarbonyl 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以56%的产率得到2-[2,3,4,5,6-五(1,3-噻唑-2-基)苯基]-1,3-噻唑
  参考文献：
  名称：

  Heterotopic Assemblage of Two Different Disk-Shaped Ligands through Trinuclear Silver(I) Complexation:  Ligand Exchange-Driven Molecular Motion

  摘要：

  The sandwich-shaped heterotopic trinuclear Ag+ complex Ag(3)1.2 was exclusively formed from two different tris(thiazolyl) and hexa(thiazolyl) disk-shaped ligands, 1 and 2, with the aid of three Ag+ ions. The variable-temperature H-1 NMR study on its complexation behavior revealed that metal-ligand exchanges between the two neighboring thiazolyl nitrogen donors of 2 take place at the three Ag+ centers in concert. DeltaH(double dagger) and DeltaS(double dagger) for the exchange process were calculated to be 50.5 kJ mol(-1) and -26.7 J mol(-1) K-1, respectively, and its energy barrier at 298 K was estimated to be 58.5 kJ mol(-1). Each concerted metal-ligand exchange leads to an intramolecular 60degrees-rotational motion ((P)reversible arrow(M) conversion) between the two disk-shaped ligands.

  DOI：

  10.1021/ja036388q
• 作为产物：
  描述：

  2-(2-(三甲基甲硅烷基)乙炔)噻唑 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 1,2-双(2-噻唑基)乙炔
  参考文献：
  名称：

  Heterotopic Assemblage of Two Different Disk-Shaped Ligands through Trinuclear Silver(I) Complexation:  Ligand Exchange-Driven Molecular Motion

  摘要：

  The sandwich-shaped heterotopic trinuclear Ag+ complex Ag(3)1.2 was exclusively formed from two different tris(thiazolyl) and hexa(thiazolyl) disk-shaped ligands, 1 and 2, with the aid of three Ag+ ions. The variable-temperature H-1 NMR study on its complexation behavior revealed that metal-ligand exchanges between the two neighboring thiazolyl nitrogen donors of 2 take place at the three Ag+ centers in concert. DeltaH(double dagger) and DeltaS(double dagger) for the exchange process were calculated to be 50.5 kJ mol(-1) and -26.7 J mol(-1) K-1, respectively, and its energy barrier at 298 K was estimated to be 58.5 kJ mol(-1). Each concerted metal-ligand exchange leads to an intramolecular 60degrees-rotational motion ((P)reversible arrow(M) conversion) between the two disk-shaped ligands.

  DOI：

  10.1021/ja036388q

文献信息

• One-Pot Domino Synthesis of Diarylalkynes/1,4-Diaryl-1,3-diynes by [9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene] (Xantphos)-Copper(I) Iodide-Palladium(II) Acetate-Catalyzed Double Sonogashira-Type Reaction
  作者：Shaozhong Qiu、Caiyang Zhang、Rui Qiu、Guodong Yin、Jinkun Huang

  DOI：10.1002/adsc.201701128

  日期：2018.1.17

  5‐bis(diphenylphosphino)xanthene] (Xantphos)copper(I) iodide and simple ligand‐free palladium(II) acetate was found to be efficient for the domino synthesis of diarylalkynes by the reaction of aryl halides with trimethylsilylethynylene or bis(trimethylsilyl)acetylene in a single‐step procedure. The unsymmetrical diarylalkynes can be obtained through a one‐pot two‐step approach. The reactions of aryl bromides

  发现复合物[9,9-二甲基-4,5-双（二苯基膦基）x吨]（Xantphos）碘化铜（I）和简单的不含配体的乙酸钯（II）的低负荷组合对于多米诺骨牌有效一步法使卤代芳基与三甲基甲硅烷基乙炔或双（三甲基甲硅烷基）乙炔反应合成二芳基炔烃。不对称二芳基炔可以通过一锅两步法获得。芳基溴化物与1,4-双（三甲基甲硅烷基）丁二炔的反应也以类似的方式提供了相应的1,4-二芳基-1,3-二炔。这种通往二芳基炔烃和1,4-二芳基-1,3-二炔烃的方法是对先前报道的合成方法的补充。
• A synthetic approach to a molecular crank mechanism: toward intramolecular motion transformation between rotation and translation
  作者：Erika Okuno、Shuichi Hiraoka、Mitsuhiko Shionoya

  DOI：10.1039/b926154k

  日期：——

  A molecular crank mechanism that enables transformation between rotational and translational motions was designed and synthesized. This molecule consists of a molecular ball bearing as the rotational part in which two disk-shaped rotors can rotate relative to each other through ligand exchange and flipping motion, and a [2]rotaxane as a translational part in which an axle molecule can move back-and-forth

  设计并合成了一种能够在旋转运动和平移运动之间进行转换的分子曲柄机制。该分子由分子球轴承作为旋转部分，其中两个盘形转子可以通过配体交换和翻转运动相对彼此旋转，而[2]轮烷作为平移部分，其中轴分子可以向后移动。通过冠醚基大环的空腔来回移动。1 H NMR分析表明这两个运动相互影响。
• Coordination-Induced Intramolecular Double Cyclization: Synthesis of Boron-Bridged Dipyridylvinylenes and Dithiazolylvinylenes
  作者：Shigehiro Yamaguchi、Qiang Zhao、Hongyu Zhang、Atsushi Wakamiya

  DOI：10.1055/s-0028-1083271

  日期：2009.1

  Di(heteroaryl)acetylenes having a pyridyl or thiazolyl as the heteroaryl group underwent a reaction with bromodibenzoborole to produce coordination complexes, which were further treated with water to promote the intramolecular cascade double cyclization to produce the dibenzoborolyl-bridged ladder di(heteroaryl)vinylenes. For the thiazolyl derivative, further derivatization at the terminal positions produced a bis(dimesitylboryl)-substituted derivative. The ladder molecules prepared showed an intense emission in the fluorescence spectra as well as reversible reduction waves at low reduction potentials in the cyclic voltammetry.

  以吡啶基或噻唑基作为杂芳基的二（杂芳基）乙炔与二溴二苯硼醚发生反应，生成配合物，再用水处理，促进分子内级联双环化反应，生成二苯硼醚桥联阶梯二（杂芳基）乙烯。对于噻唑基衍生物，在末端位置进一步衍生，生成双（二甲基硼酰基）取代衍生物。制备的阶梯分子在荧光光谱中显示出强烈的发射，在循环伏安法中，在低还原电位下出现可逆还原波。
• UV EMITTERS COMPRISING A MULTIPLE BOND
  申请人：MERCK PATENT GMBH

  公开号：US20150340612A1

  公开（公告）日：2015-11-26

  The invention relates to organic electroluminescent devices comprising organic compounds with a double or triple bond, to which at least one aromatic ring is bonded, as emitter compounds. The invention also relates to possible uses of said devices.

  本发明涉及含有双键或三键的有机化合物作为发光化合物，其中至少一个芳香环与之键合的有机电致发光器件。本发明还涉及所述器件的可能用途。
• Ranging Correlated Motion (1.5 nm) of Two Coaxially Arranged Rotors Mediated by Helix Inversion of a Supramolecular Transmitter
  作者：Shuichi Hiraoka、Erika Okuno、Takaaki Tanaka、Motoo Shiro、Mitsuhiko Shionoya

  DOI：10.1021/ja8014583

  日期：2008.7.1

  For a long-range transmission of motion between two movable parts apart from each other, transmitters that can precisely correlate these two motions should be properly incorporated into the system. However, such a motional relay is yet to be realized in artificial systems because of the lack of reliable methodologies for arranging a discrete number of motional parts. Herein, we report a correlated motion of two rotor molecules, which are coaxially arranged at a distance of 1.5 nm, through either Ag+- or Hg2+-assembled helical transmitters, leading to different frequencies of synchronized motion. A helix inversion in the transmitter was proven to strongly correlate the motions of both terminals. The X-ray analysis of the entity determined a quadruple-decker nonanuclear structure of the metal complex comprising two terminal rotor-like ligands closely attached to a central transmitter moiety. H-1 NMR analysis fully demonstrated the synchronized motion of the two rotors coaxially stacked and connected through the transmitter. Since the transmitter is composed of simple helical repeating units, the principle of helix inversion would be an efficient and widely applicable strategy for the long-range transmission of molecular motion.