2-methylene-6-heptynoic acid | 127559-94-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-methylene-6-heptynoic acid
• 英文别名: 2-Methylidenehept-6-ynoic acid
• CAS: 127559-94-8
• 化学式: C₈H₁₀O₂
• mdl: MFCD19229612
• 分子量: 138.166
• InChiKey: HOUNDUJXSJIDAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylene-6-heptynoic 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 2-methylene-6-heptynoic 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：

  1,6-庚二炔 在 tris(2,2'-bipyridine)nickel(II) tetrafluoroborate 、 二氧化碳 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 65.0 ℃ 、101.32 kPa 条件下， 以4.5%的产率得到2-methylene-6-heptynoic acid
  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

文献信息

• Electrogenerated nickel(0) catalyzed carbon dioxide incorporation into α,ω-diynes
  作者：S. Dérien、E. Duñach、J. Périchon

  DOI：10.1016/0022-328x(90)85018-t

  日期：1990.3
• 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.