2-(2,3,4-triethyl-5-oxo-2,5-dihydrofuran-2-yl)butyric acid | 1354966-67-8

• 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-(2,3,4-triethyl-5-oxo-2,5-dihydrofuran-2-yl)butyric acid
• 英文别名: 2-(2,3,4-Triethyl-5-oxofuran-2-yl)butanoic acid；2-(2,3,4-triethyl-5-oxofuran-2-yl)butanoic acid
• CAS: 1354966-67-8
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: CNGIRWSHXQLIQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Ni[C(Et)=C(Et)-COO](2,2'-bipyridine) 在 N-溴代丁二酰亚胺(NBS) 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 生成 2-(2,3,4-triethyl-5-oxo-2,5-dihydrofuran-2-yl)butyric acid 、 (Z)-3-bromo-2-ethylpent-2-enoic acid
  参考文献：
  名称：

  Nickelacyclic carboxylates derived from 3-hexyne and CO2 and their application in the synthesis of a new muconic acid derivative

  摘要：

  The mononuclear unsaturated nickelalactones [Ni{C(Et)=C(Et)-COO}( DBU)(2)] (1) and [Ni{C(Et)=C(Et)-COO}(dcpe)] (2) were synthesized by oxidative coupling of CO2 and 3-hexyne at zero-valent nickel in presence of DBU or dpce, respectively. Attempts to use Cy3P or dppe as ligands in this reaction gave the zero-valent complex [Ni(cy(3)P)(2)(eta(2)-3-hexyne)] (3) and the well known [Ni(dppe)(2)] instead. However, the dppe stabilized unsaturated nickelalactone [Ni{C(Et)=C(Et)-COO}(dppe)] (4) was synthesized from the corresponding 2,2'-bipyridine complex by ligand displacement with dppe. Complex 1 is a useful synthon for the synthesis of carboxylic acid derivatives, as shown by its reaction with NBS leading to 3-bromo-2-ethyl-pent-2-enoic acid in good yield. On the contrary, the reaction between [Ni{C(Et)=C(Et)-COO}(bipy)] and NBS gave the hitherto unknown 2-(2,3,4-triethyl-5-oxo-2,5-dihydrofuran-2-yl)butyric acid (5) as major product. Compounds 1-5 were structurally investigated by NMR and IR spectroscopy and in the solid state by X-ray diffraction analysis of single crystals. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.05.047