2-methoxy-2-[(methoxycarbonyl)methyl]tetrahydrofuran | 146346-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methoxy-2-[(methoxycarbonyl)methyl]tetrahydrofuran
• 英文别名: Methyl 2-(2-methoxyoxolan-2-yl)acetate
• CAS: 146346-38-5
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: DOZAAUYDTDCWRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲醇 、 methyl 6-oxo-2-hexenoate 在 copper(l) chloride 、 copper dichloride 、 palladium dichloride 氧气 作用下， 反应 22.0h， 以62%的产率得到2-methoxy-2-[(methoxycarbonyl)methyl]tetrahydrofuran
  参考文献：
  名称：

  Rate enhancement in the Wacker oxidation of hydroxy-α,β-unsaturated esters: A fast neutral method for the preparation of masked β-ketoesters

  摘要：

  DOI：

  10.1016/0040-4039(93)88033-f

文献信息

• Palladium-catalyzed synthesis of 2E-[(methoxycarbonyl)methylene]tetrahydrofurans: oxidative cyclization–methoxycarbonylation of 4-yn-1-ols versus cycloisomerization–hydromethoxylation
  作者：Bartolo Gabriele、Giuseppe Salerno、Francesca De Pascali、Mirco Costa、Gian Paolo Chiusoli

  DOI：10.1016/s0022-328x(99)00492-1

  日期：2000.1

  4-Yn-1-ols bearing a terminal triple bond undergo oxidative cyclization-alkoxycarbonylation in methanol at 70 degrees C and 100 atm of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of [PdI4](2-) in conjunction with an excess of KI to give 2E-[(methoxycarbonyl)methylene]tetrahydrofurans in good yields. A competing reaction, cycloisomerization-hydromethoxylation leading to 2-methoxy-2-methyltetrahydrofurans, can be easily curtailed by increasing the KI excess. The latter products can be prepared from 4-yn-1-ols and methanol in high yields using the same catalytic system and without KI excess in the absence of carbon monoxide. (C) 2000 Elsevier Science S.A. All rights reserved.