(E)-2-(phenylethynyl)-4-methoxy-2-butenoic acid | 134889-89-7

• 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: (E)-2-(phenylethynyl)-4-methoxy-2-butenoic acid
• 英文别名: (E)-4-methoxy-2-(2-phenylethynyl)but-2-enoic acid
• CAS: 134889-89-7
• 化学式: C₁₃H₁₂O₃
• 分子量: 216.236
• InChiKey: SROOVCNEUQSLFS-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(phenylethynyl)-4-methoxy-2-butenoic acid 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (E)-2-(phenylethynyl)-4-methoxy-2-butenoic acid methyl ester
  参考文献：
  名称：

  Activation of carbon dioxide: nickel-catalyzed electrochemical carboxylation of diynes

  摘要：

  The simultaneous activation of carbon dioxide and diynes by electrogenerated LNi(0) complexes (L = bpy, pentamethyldiethylenetriamine: PMDTA) enables the selective incorporation of one molecule of CO2 into the unsaturated systems and the preparative-scale electrosyntheses of carboxylic acids. A series of nonconjugated diynes afforded selectively linear or cyclic adducts depending on the ligand. Diynes bearing both a terminal and an internal triple bond gave exclusive CO2 incorporation into the terminal alkynyl group, regioselectively at the 2-position. The electrocarboxylation of 1,3-diynes with the Ni-PMDTA catalytic system yielded, regio- and stereoselectively, (E)-2-vinylidene-3-yne carboxylic acids in one step. The electrosyntheses were carried out in single-compartment cells fitted with a consumable magnesium anode, and utilized a catalytic amount of an air-stable Ni(II) complex as the catalyst precursor. Cyclic voltammetry studies revealed that both carbon dioxide and the diynes are able to coordinate to LNi(0)-generated species in DMF.

  DOI：

  10.1021/jo00061a038
• 作为产物：
  描述：

  二氧化碳 、 (5-methoxypenta-1,3-diyn-1-yl)benzene 在 乙二醇二甲醚 、 五甲基二乙烯三胺 、 tetrabutylammonium tetrafluoroborate 、 nickel dibromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、506.62 kPa 条件下， 反应 7.0h， 生成 (E)-2-(phenylethynyl)-4-methoxy-2-butenoic acid 、 5-Methoxy-2-[1-phenyl-meth-(E)-ylidene]-pent-3-ynoic acid
  参考文献：
  名称：

  First example of direct carbon dioxide incorporation into 1,3-diynes: a highly regio- and stereo-selective nickel-catalysed electrochemical reaction

  摘要：

  从二氧化碳和取代的1,3-二炔合成2-乙烯基-3-炔羧酸的电合成反应，在镍-三胺配合物的催化下，结果是对一个三键的区域选择性和立体选择性加成。

  DOI：

  10.1039/c39910000549

文献信息

• First example of direct carbon dioxide incorporation into 1,3-diynes: a highly regio- and stereo-selective nickel-catalysed electrochemical reaction
  作者：Sylvie Dérien、Jean-Claude Clinet、Elisabet Duñach、Jacques Périchon

  DOI：10.1039/c39910000549

  日期：——

  The electrosynthesis of 2-vinylidene-3-yne carboxylic acids from carbon dioxide and substituted 1,3-diynes is catalysed by a nickel–triamine complex and results in a regio- and stereo-selective addition to one triple bond.

  从二氧化碳和取代的1,3-二炔合成2-乙烯基-3-炔羧酸的电合成反应，在镍-三胺配合物的催化下，结果是对一个三键的区域选择性和立体选择性加成。
• Activation of carbon dioxide: nickel-catalyzed electrochemical carboxylation of diynes
  作者：Sylvie Derien、Jean Claude Clinet、Elisabet Dunach、Jacques Perichon

  DOI：10.1021/jo00061a038

  日期：1993.4

  The simultaneous activation of carbon dioxide and diynes by electrogenerated LNi(0) complexes (L = bpy, pentamethyldiethylenetriamine: PMDTA) enables the selective incorporation of one molecule of CO2 into the unsaturated systems and the preparative-scale electrosyntheses of carboxylic acids. A series of nonconjugated diynes afforded selectively linear or cyclic adducts depending on the ligand. Diynes bearing both a terminal and an internal triple bond gave exclusive CO2 incorporation into the terminal alkynyl group, regioselectively at the 2-position. The electrocarboxylation of 1,3-diynes with the Ni-PMDTA catalytic system yielded, regio- and stereoselectively, (E)-2-vinylidene-3-yne carboxylic acids in one step. The electrosyntheses were carried out in single-compartment cells fitted with a consumable magnesium anode, and utilized a catalytic amount of an air-stable Ni(II) complex as the catalyst precursor. Cyclic voltammetry studies revealed that both carbon dioxide and the diynes are able to coordinate to LNi(0)-generated species in DMF.