1-ethoxycarbonylmethyl-4-(4'-pyridyl)pyridinium bromide | 97318-91-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-ethoxycarbonylmethyl-4-(4'-pyridyl)pyridinium bromide
• 英文别名: N-[1-(2-ethoxy-2-oxo)ethyl]-4,4'-bipyridynium bromide；1-(2-Ethoxy-2-oxoethyl)-4-(4-pyridinyl)pyridinium bromide；ethyl 2-(4-pyridin-4-ylpyridin-1-ium-1-yl)acetate;bromide
• CAS: 97318-91-7
• 化学式: Br*C₁₄H₁₅N₂O₂
• 分子量: 323.189
• InChiKey: CAYFOQFTFUYOFH-UHFFFAOYSA-M

物化性质

• 熔点：
  >350 °C(Solv: ethanol (64-17-5))

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-ethoxycarbonylmethyl-4-(4'-pyridyl)pyridinium bromide 在 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 72.0h， 生成 1,1'-(1-ethoxycarbonyl-1'-cyano-1,1'-benzoyl)-4,4'-bipyridinium dimethylide
  参考文献：
  名称：

  Synthesis and Characterisation of Extended p-Bonding Systems in Cycloimmonium Ylides Derived from the 4,4’-Bipyridine

  摘要：

  Disubstituted cycloimmonium ylides derived from the 4,4'-bipyridine with one, two or four ylidic systems in their molecular structure are described as stable compounds. Synthesis of some bridged 1,1'-disubstituted 4,4'-bipyridinium dimethylides in which 1,4- or 1,3-phenylene spacers may be used, provide some new macromolecular cycloimmonium ylides with spatially extended pi-bonding system. These compounds were obtained by the chemical conversion of 4,4'-bipyridinium salts as viologens or bis-viologens, with acylating or carbamoylating agents, in basic media. The characterisation of all compounds has been mainly performed by H-1 and C-13 NMR spectroscopy.

  DOI：

  10.3987/com-02-9571
• 作为产物：
  描述：

  4,4'-联吡啶 、 溴乙酸乙酯 以 丙酮 为溶剂， 反应 3.0h， 生成 1-ethoxycarbonylmethyl-4-(4'-pyridyl)pyridinium bromide
  参考文献：
  名称：

  一种新型的耦合1，3-偶极环加成序列作为三组分方法的高荧光吲哚嗪

  摘要：

  吲哚嗪4和联吲哚嗪6可以通过（杂）芳烃羰基氯1，末端炔烃2和合适的1的偶合/ 1,3-偶极环加成序列，以连续的一锅三组分法以中等收率合成。-（2-氧乙基）吡啶鎓溴化物3或5（方案1和2）。在Sonogashira耦合之后，原位[2 + 3]环加成形成的吡啶鎓内鎓盐（一种烯丙基型1,3偶极子）提供了一种环加合物，该环加合物被瞬间氧化芳构化，以给出高荧光的吲哚嗪衍生物，其明确地由化合物4d的X射线结构分析表征（图1）。另外，用吡啶基取代的代表进行的荧光研究不仅表明吲哚嗪和联吲哚嗪是非常有趣的荧光染料，而且它们的荧光颜色也可以在改变培养基的pH值时可逆地转换。

  DOI：

  10.1002/hlca.200590141

文献信息

• 1,3-Dipolar cycloaddition reaction of bipyridinium ylides with the propynamido-β-cyclodextrin. A regiospecific synthesis of a new class of fluorescent β-cyclodextrins
  作者：François Delattre、Patrice Woisel、Gheorghe Surpateanu、Marc Bria、Francine Cazier、Patrick Decock

  DOI：10.1016/j.tet.2003.12.006

  日期：2004.2

  The 1,3-dipolar cycloaddition reaction of bipyridinium ylides with the electron deficient propynamido-β-cyclodextrin was studied. This reaction resulted in the regiospecific formation of a new class of fluorescent β-cyclodextrins. The new fluorophore systems were characterized spectroscopically by their absorption and emission maxima and their quantum yields.

  研究了联吡啶鎓与电子缺陷的丙酰胺基-β-环糊精的1,3-偶极环加成反应。该反应导致新型荧光β-环糊精的区域特异性形成。新的荧光团系统的光谱学特征是其最大吸收和发射量以及其量子产率。
• A Novel Coupling 1,3-Dipolar Cycloaddition Sequence as a Three-Component Approach to Highly Fluorescent Indolizines
  作者：Alexandru V. Rotaru、Ioan D. Druta、Thomas Oeser、Thomas J. J. Müller

  DOI：10.1002/hlca.200590141

  日期：2005.7

  Indolizines 4 and biindolizines 6 can be synthesized in moderate yields in a consecutive one-pot three-component process by a coupling/1,3-dipolar cycloaddition sequence of a (hetero)arenecarbonyl chloride 1, a terminal alkyne 2, and a suitable 1-(2-oxoethyl) pyridinium bromide 3 or 5, respectively (Schemes 1 and 2). After the Sonogashira coupling, a [2+3] cycloaddition of the in situ formed pyridinium

  吲哚嗪4和联吲哚嗪6可以通过（杂）芳烃羰基氯1，末端炔烃2和合适的1的偶合/ 1,3-偶极环加成序列，以连续的一锅三组分法以中等收率合成。-（2-氧乙基）吡啶鎓溴化物3或5（方案1和2）。在Sonogashira耦合之后，原位[2 + 3]环加成形成的吡啶鎓内鎓盐（一种烯丙基型1,3偶极子）提供了一种环加合物，该环加合物被瞬间氧化芳构化，以给出高荧光的吲哚嗪衍生物，其明确地由化合物4d的X射线结构分析表征（图1）。另外，用吡啶基取代的代表进行的荧光研究不仅表明吲哚嗪和联吲哚嗪是非常有趣的荧光染料，而且它们的荧光颜色也可以在改变培养基的pH值时可逆地转换。
• Avram, Ecaterina; Lisa, Gabriela, Revue Roumaine de Chimie, 2008, vol. 53, # 9, p. 759 - 768
  作者：Avram, Ecaterina、Lisa, Gabriela

  DOI：——

  日期：——
• Synthesis and Characterisation of Extended p-Bonding Systems in Cycloimmonium Ylides Derived from the 4,4’-Bipyridine
  作者：Ludovic Depature、Gheorghe Surpateanu

  DOI：10.3987/com-02-9571

  日期：——

  Disubstituted cycloimmonium ylides derived from the 4,4'-bipyridine with one, two or four ylidic systems in their molecular structure are described as stable compounds. Synthesis of some bridged 1,1'-disubstituted 4,4'-bipyridinium dimethylides in which 1,4- or 1,3-phenylene spacers may be used, provide some new macromolecular cycloimmonium ylides with spatially extended pi-bonding system. These compounds were obtained by the chemical conversion of 4,4'-bipyridinium salts as viologens or bis-viologens, with acylating or carbamoylating agents, in basic media. The characterisation of all compounds has been mainly performed by H-1 and C-13 NMR spectroscopy.
• Multi-Stimuli-Responsive Chromic Behaviors of an All–in–One Viologen-Based Cd(II) Complex
  作者：Yun Luo、Jia-Pei Liu、Lin-Ke Li、Shuang-Quan Zang

  DOI：10.1021/acs.inorgchem.3c02070

  日期：2023.9.4

  A one-dimensional Cd(II) chain coordination polymer constructed by an electron-deficient viologen-anchored carboxylate ligand was successfully synthesized. Owing to the favorable stimuli-chromic properties of viologen, the title compound shows reversible photochromism, thermochromism, electrochromism, and naked-eye-detectable differentiable vapochromic response to different volatile amines. The chromic

  成功合成了由缺电子紫精锚定的羧酸配体构建的一维Cd(II)链配位聚合物。由于紫精良好的刺激致变色特性，标题化合物对不同的挥发性胺表现出可逆的光致变色、热致变色、电致变色和肉眼可检测的可微分气致变色响应。其变色行为归因于外部刺激引发的紫精自由基的形成。而对挥发性胺的差异化反应归因于胺的尺寸效应以及紫精单元形成α/β C v –H…N胺相互作用的空间位阻效应，进一步影响电子转移的发生。这种一体式晶体材料可能在光电、可擦无墨印刷、光印刷和挥发性胺检测领域有更实际的应用。