(5-oxo-tetrahydrofuran-2-yl)methyl thiophene-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (5-oxo-tetrahydrofuran-2-yl)methyl thiophene-2-carboxylate
• 英文别名: (5-Oxooxolan-2-yl)methyl thiophene-2-carboxylate
• 化学式: C₁₀H₁₀O₄S
• 分子量: 226.253
• InChiKey: IFECEZAIMKRVCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-戊烯酸 、 lead tetra(thiophenecarboxylate) 以 甲苯 为溶剂， 反应 3.0h， 以84%的产率得到(5-oxo-tetrahydrofuran-2-yl)methyl thiophene-2-carboxylate
  参考文献：
  名称：

  Novel alkylation, lactonisation and cascade coupling processes mediated by lead tetracarboxylates: the importance of ligands

  摘要：

  The reactions of lead(IV) tetracarboxylates with carboxylic acids containing unsaturated side chains is reported. At elevated temperature in toluene, facile decarboxylation or lactonisation processes are observed, depending on the length of the carboxylate side chain and in some cases further cascade coupling processes with added nucleophiles are possible. The efficiency of these processes depends on the structure of the carboxylate ligand and the mechanistic implications of these results are briefly discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02288-2

文献信息

• Acyloxylactonisations mediated by lead tetracarboxylates
  作者：Ian F. Cottrell、Andrew R. Cowley、Laura J. Croft、Lauren Hymns、Mark G. Moloney、Ewan J. Nettleton、H. Kirsty Smithies、Amber L. Thompson

  DOI：10.1016/j.tet.2009.01.042

  日期：2009.3

  The reaction of lead(IV) tetracarboxylates with carboxylic acids containing unsaturated side chains has been found to give acyloxy lactone products in a diastereoselective process; the reaction can be extended to lead(IV) tetrazolates to give the analogous outcome. Mechanistic implications of these results are discussed. (C) 2009 Elsevier Ltd. All rights reserved.