4,4,5,5,6,6,7,7,8,8,8-Undecafluoro-2-diazo-3-oxooctanoic acid ethyl ester | 283586-99-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,4,5,5,6,6,7,7,8,8,8-Undecafluoro-2-diazo-3-oxooctanoic acid ethyl ester
• 英文别名: Ethyl 2-diazo-4,4,5,5,6,6,7,7,8,8,8-undecafluoro-3-oxooctanoate；ethyl 2-diazo-4,4,5,5,6,6,7,7,8,8,8-undecafluoro-3-oxooctanoate
• CAS: 283586-99-2
• 化学式: C₁₀H₅F₁₁N₂O₃
• 分子量: 410.144
• InChiKey: FOBXXDNKHPBNHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  间甲基苯腈 、 4,4,5,5,6,6,7,7,8,8,8-Undecafluoro-2-diazo-3-oxooctanoic acid ethyl ester 在 dirhodium tetraacetate 作用下， 以42%的产率得到4-Carbethoxy-2-(3-m-tolyl)-5-perfluoropentyloxazole
  参考文献：
  名称：

  A rhodium-catalyzed heterocycloaddition route to 5-fluoroalkyl substituted 1,3-oxazoles

  摘要：

  In the presence of catalytic rhodium (II) acetate, ethyl 2-diazo-fluoroalkylacetoacetate, obtained from the reaction of ethyl fluoroalkylacetoacetate with perfluoroalkanesulfonyl azide or tosyl azide, reacted readily with nitriles to give a series of 5-fluoroalkyl substituted 1,3-oxazoles in fair to good yields. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(99)00306-1
• 作为产物：
  描述：

  dihydro-2,2 oxo-3 F-octanoate d'ethyle 在 polyfluoroalkanesulfonyl azide 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 4,4,5,5,6,6,7,7,8,8,8-Undecafluoro-2-diazo-3-oxooctanoic acid ethyl ester
  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.
• A rhodium-catalyzed heterocycloaddition route to 5-fluoroalkyl substituted 1,3-oxazoles
  作者：Yanli Wang、Shizheng Zhu

  DOI：10.1016/s0022-1139(99)00306-1

  日期：2000.4

  In the presence of catalytic rhodium (II) acetate, ethyl 2-diazo-fluoroalkylacetoacetate, obtained from the reaction of ethyl fluoroalkylacetoacetate with perfluoroalkanesulfonyl azide or tosyl azide, reacted readily with nitriles to give a series of 5-fluoroalkyl substituted 1,3-oxazoles in fair to good yields. (C) 2000 Elsevier Science S.A. All rights reserved.