ethyl 2-bromodifluoromethyl-5-iso-butoxy-4,5-dihydro-3-furancarboxylate | 347341-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: ethyl 2-bromodifluoromethyl-5-iso-butoxy-4,5-dihydro-3-furancarboxylate
• 英文别名: Ethyl 5-[bromo(difluoro)methyl]-2-(2-methylpropoxy)-2,3-dihydrofuran-4-carboxylate；ethyl 5-[bromo(difluoro)methyl]-2-(2-methylpropoxy)-2,3-dihydrofuran-4-carboxylate
• CAS: 347341-04-2
• 化学式: C₁₂H₁₇BrF₂O₄
• 分子量: 343.165
• InChiKey: OQIVHIBZYUMLNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-bromodifluoromethyl-5-iso-butoxy-4,5-dihydro-3-furancarboxylate 在 硫酸 作用下， 以 四氯化碳 为溶剂， 以38%的产率得到ethyl 3-bromodifluoromethyl-2-furancarboxylate
  参考文献：
  名称：

  A simple synthesis of fluoroalkyl substituted dihydrofurans by rhodium(II)-catalyzed 1,3-dipolar reactions

  摘要：

  The rhodium(II)-catalyzed reactions of ethyl 2-diazo-fluoroalkylacetoacetate 1 with vinyl ethers have been studied. The reactions of 1a-e with isobutyl vinyl ethers afforded dihydrofuroates 3a-e in good to excellent yields. Further transformation of the dihydrofuroates by acid-catalyzed alcohol elimination could give alpha -fluoroalkyl-beta -furoates readily. Similarly, stable diazo compounds 1a and b reacted with cyclic vinyl ethers to give 1,3-dipolar cycloaddition products. Interestingly, only vinyl C-H insertion compound was obtained concerning the reaction of la with 2,5-dimethylfuran. The reaction mechanism was also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00183-1
• 作为产物：
  描述：

  ethyl 4-bromo-4,4-difluoro-3-oxo-butanoate 在 Ph₂(OAc)4 对甲苯磺酰叠氮 作用下， 生成 ethyl 2-bromodifluoromethyl-5-iso-butoxy-4,5-dihydro-3-furancarboxylate
  参考文献：
  名称：

  A simple synthesis of fluoroalkyl substituted dihydrofurans by rhodium(II)-catalyzed 1,3-dipolar reactions

  摘要：

  The rhodium(II)-catalyzed reactions of ethyl 2-diazo-fluoroalkylacetoacetate 1 with vinyl ethers have been studied. The reactions of 1a-e with isobutyl vinyl ethers afforded dihydrofuroates 3a-e in good to excellent yields. Further transformation of the dihydrofuroates by acid-catalyzed alcohol elimination could give alpha -fluoroalkyl-beta -furoates readily. Similarly, stable diazo compounds 1a and b reacted with cyclic vinyl ethers to give 1,3-dipolar cycloaddition products. Interestingly, only vinyl C-H insertion compound was obtained concerning the reaction of la with 2,5-dimethylfuran. The reaction mechanism was also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00183-1

文献信息

• A simple synthesis of fluoroalkyl substituted dihydrofurans by rhodium(II)-catalyzed 1,3-dipolar reactions
  作者：Yanli Wang、Shizheng Zhu

  DOI：10.1016/s0040-4020(01)00183-1

  日期：2001.4

  The rhodium(II)-catalyzed reactions of ethyl 2-diazo-fluoroalkylacetoacetate 1 with vinyl ethers have been studied. The reactions of 1a-e with isobutyl vinyl ethers afforded dihydrofuroates 3a-e in good to excellent yields. Further transformation of the dihydrofuroates by acid-catalyzed alcohol elimination could give alpha -fluoroalkyl-beta -furoates readily. Similarly, stable diazo compounds 1a and b reacted with cyclic vinyl ethers to give 1,3-dipolar cycloaddition products. Interestingly, only vinyl C-H insertion compound was obtained concerning the reaction of la with 2,5-dimethylfuran. The reaction mechanism was also discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.