1,4-bis(2-ethynylphenylethynyl)benzene | 305350-56-5

• 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: 1,4-bis(2-ethynylphenylethynyl)benzene
• 英文别名: 1,4-Bis[(2-ethynylphenyl)ethynyl]benzene；1,4-bis[2-(2-ethynylphenyl)ethynyl]benzene
• CAS: 305350-56-5
• 化学式: C₂₆H₁₄
• 分子量: 326.397
• InChiKey: NBIQMVIHLWWUGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• 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：

  1,4-bis(2-ethynylphenylethynyl)benzene 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 氘代氯仿 、 乙腈 为溶剂， 反应 21.5h， 生成
  参考文献：
  名称：

  Enantioselective Sensing of Amines Based on [1 + 1]-, [2 + 2]-, and [1 + 2]-Condensation with Fluxional Arylacetylene-Derived Dialdehydes

  摘要：

  Four induced circular dichroism (ICD) probes exhibiting a stereodynamic arylacetylene framework and terminal aldehyde units have been prepared. The CD silent sensors generate a strong chlroptical response to substrate-controlled induction of axial chirality upon selective [1 + 1]-, [2 + 2]-, and [1 + 2]-condensation. The Intense Cotton effects can be exploited for In situ ICD analysis of the absolute configuration and ee of a wide range of amines.

  DOI：

  10.1021/ol200574x
• 作为产物：
  描述：

  2-溴苯乙炔 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 trans-bis(acetonitrile)palladium(II) chloride 、 四丁基氟化铵 、 三乙胺 、 二异丙胺 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 1,4-bis(2-ethynylphenylethynyl)benzene
  参考文献：
  名称：

  通过含手性亚砜的o - OPEs与金属阳离子的亲氧相互作用，可对圆偏振发光进行OFF / ON切换†

  摘要：

  在这里，我们基于含手性亚砜的邻亚苯基亚乙炔基（o- OPE）折叠剂与阳离子金属之间的亲氧相互作用，描述了一类新的CPL开关。这些系统代表了一种独特的情况，在折叠的CPL状态和未折叠的CPL状态下都具有高g lum值（高达0.7×10 -2）和高量子产率。

  DOI：

  10.1039/c8cc08395a

文献信息

• Synthesis of Novel Acetylenic Cyclophanes with Helical Chirality:  Potential New Structures for Liquid Crystals
  作者：Shawn K. Collins、Glenn P. A. Yap、Alex G. Fallis

  DOI：10.1021/ol000199k

  日期：2000.10.1

  The synthesis of a series of novel acetylenic cyclophanes is described. X-ray crystallographic analysis of the core structure revealed a twisted conformation with helical chirality. Preliminary results suggest that these cyclophanes, with appropriate functionality, have the potential to act as unique liquid crystalline materials.

  描述了一系列新型炔属环烷的合成。核心结构的X射线晶体学分析显示出具有螺旋手性的扭曲构象。初步结果表明，这些具有适当功能的环烷具有充当独特液晶材料的潜力。
• Enantioselective sensing of chiral amino alcohols with a stereodynamic arylacetylene-based probe
  作者：Daniel P. Iwaniuk、Keith W. Bentley、Christian Wolf

  DOI：10.1002/chir.22066

  日期：2012.7

  aldehyde groups. The chirality of the amino alcohol substrates is imprinted on the stereodynamic receptor upon [1 + 2] condensation, which ultimately generates a strong chiroptical response. The distinct induced circular dichroism effects of the diimines obtained can be used for enantioselective sensing and enantiomeric excess determination of a wide range of substrates. Chirality 24:584–589, 2012. ©

  使用具有两个末端醛基的构象柔性基于芳基乙炔的探针已完成了对氨基醇的对映选择性诱导的二色性分析。氨基醇底物的手性在[1 + 2]缩合时被印在立体动力受体上，最终产生强烈的手性反应。所获得的二亚胺的独特的诱导的二色性圆二色性效应可用于多种底物的对映选择性传感和对映体过量测定。手性24：584–589，2012年。分级为4 +©2012 Wiley Periodicals，Inc.
• Chirality Sensing With Stereodynamic Biphenolate Zinc Complexes
  作者：Keith W. Bentley、Zeus A. Santos、Mary J. Weiss、Christian Wolf

  DOI：10.1002/chir.22489

  日期：2015.10

  polyarylacetylene framework with terminal phenol groups were synthesized. Reaction with diethylzinc gives stereodynamic complexes that undergo distinct asymmetric transformation of the first kind upon binding of chiral amines and amino alcohols. The substrate‐to‐ligand chirality imprinting at the zinc coordination sphere results in characteristic circular dichroism signals that can be used for direct enantiomeric

  合成了由具有末端酚基的助熔聚芳基乙炔骨架组成的两个双齿配体。与二乙基锌反应生成立体动力学复合物，该复合物在手性胺和氨基醇结合后会经历明显的第一类不对称转化。锌配位体上的底物-配体手性印迹产生了特征性的二向色性信号，可用于直接对映体过量（ee）分析。与传统的高效液相色谱方法相比，这种化学传感方法具有以少量样品进行高通量ee筛选的潜力，并减少了溶剂浪费。手性27：700–707，2015。©2015 Wiley Periodicals，Inc.
• A Stereodynamic Probe Providing a Chiroptical Response to Substrate-Controlled Induction of an Axially Chiral Arylacetylene Framework
  作者：Daniel P. Iwaniuk、Christian Wolf

  DOI：10.1021/ja111583e

  日期：2011.3.2

  A stereodynamic probe containing a central 1,4-di(phenylethynyl)benzene rod and two 2-formylphenylethynyl branches has been prepared through a series of Sonogashira cross-coupling reactions with 62% overall yield. This CD silent diarylacetylene-based framework carries two terminal aldehyde groups and provides a strong chiroptical response to substrate-controlled induction of three chiral axes upon diimine formation. The chiral amplification results in intense Cotton effects that can be used for in situ ICD analysis of the absolute configuration and ee of a wide range of amines.
• Enantioselective Sensing of Amines Based on [1 + 1]-, [2 + 2]-, and [1 + 2]-Condensation with Fluxional Arylacetylene-Derived Dialdehydes
  作者：Daniel P. Iwaniuk、Christian Wolf

  DOI：10.1021/ol200574x

  日期：2011.5.20

  Four induced circular dichroism (ICD) probes exhibiting a stereodynamic arylacetylene framework and terminal aldehyde units have been prepared. The CD silent sensors generate a strong chlroptical response to substrate-controlled induction of axial chirality upon selective [1 + 1]-, [2 + 2]-, and [1 + 2]-condensation. The Intense Cotton effects can be exploited for In situ ICD analysis of the absolute configuration and ee of a wide range of amines.