(1R,2R,4S,5S)-6,6,7,7-Tetrafluoro-3-oxa-bicyclo[3.2.0]heptane-2,4-dicarboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,2R,4S,5S)-6,6,7,7-Tetrafluoro-3-oxa-bicyclo[3.2.0]heptane-2,4-dicarboxylic acid
• 英文别名: (1S,2S,4R,5R)-6,6,7,7-tetrafluoro-3-oxabicyclo[3.2.0]heptane-2,4-dicarboxylic acid
• 化学式: C₈H₆F₄O₅
• 分子量: 258.126
• InChiKey: ZBYYITGKQLENSW-GNSDDBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,5S)-6,6,7,7-Tetrafluoro-3-oxa-bicyclo[3.2.0]heptane-2,4-dicarboxylic acid 在 sulfur tetrafluoride 作用下， 反应 7.5h， 以36%的产率得到(1S,2S,4R,5R)-6,6,7,7-Tetrafluoro-2,4-bis-trifluoromethyl-3-oxa-bicyclo[3.2.0]heptane
  参考文献：
  名称：

  Fluorocyclisation of 2,5-tetrahydrofurandicarboxylic and 2,3,4,5-tetrahydrofurantetracarboxylic acids with sulphur tetrafluoride leading to bicyclic and tricyclic fluoroethers

  摘要：

  cis-2,5-Tetrahydrofurandicarboxylic acid (1) reacts with sulphur tetrafluoride to give comparable amounts of 2,5-bis(trifluoromethyl) tetrahydrofuran (2) and the bicyclic tetrafluoroether, 2,2,4,4-tetrafluoro-3,8-dioxa-bicyclo [3.2.1]octane (3). Cyclisation of cis-2,5-carboxylic groups leading to the tricyclic fluoroethers, exo-3,3,5,5,8,8,9,9-octafluoro-4,10-dioxatricyclo[5.2.1.01(,7)] decane (6) and exo-3,3,5,5,8,8,10,10-octafluoro-4,9,11-trioxatricyclo[5.3.1.0(1,7)] undecane (9) was also found to be the main or equivalent course of the reactions of 3,4-tetrafluoroethano-cis-2,5-tetrahydrofurandicarboxylic acid ( 4) and trans,cis, trans-2,3,4,5-tetrahydrofurantetracarboxylicacid (7); the bis(trifluoromethyl) derivatives, exo-cis-2,4-bis(trifluoromethyl)-6,6,7,7-tetrafluoro-3-oxabicyclo [3.2.0]heptane (5) and exo-cis-2,4-bis(trifluoromethyl) -6,6,8,8-tetrafluoro-3,7-dioxabicyclo [3.3.0]heptane (8) are formed in lower or comparable amounts. (C) 1997 Elsevier Science S.A.

  DOI：

  10.1016/s0022-1139(97)00084-5

文献信息

• Fluorocyclisation of 2,5-tetrahydrofurandicarboxylic and 2,3,4,5-tetrahydrofurantetracarboxylic acids with sulphur tetrafluoride leading to bicyclic and tricyclic fluoroethers
  作者：Yurii M. Pustovit、Wojciech Dmowski、Valéry Nazaretian

  DOI：10.1016/s0022-1139(97)00084-5

  日期：1997.10

  cis-2,5-Tetrahydrofurandicarboxylic acid (1) reacts with sulphur tetrafluoride to give comparable amounts of 2,5-bis(trifluoromethyl) tetrahydrofuran (2) and the bicyclic tetrafluoroether, 2,2,4,4-tetrafluoro-3,8-dioxa-bicyclo [3.2.1]octane (3). Cyclisation of cis-2,5-carboxylic groups leading to the tricyclic fluoroethers, exo-3,3,5,5,8,8,9,9-octafluoro-4,10-dioxatricyclo[5.2.1.01(,7)] decane (6) and exo-3,3,5,5,8,8,10,10-octafluoro-4,9,11-trioxatricyclo[5.3.1.0(1,7)] undecane (9) was also found to be the main or equivalent course of the reactions of 3,4-tetrafluoroethano-cis-2,5-tetrahydrofurandicarboxylic acid ( 4) and trans,cis, trans-2,3,4,5-tetrahydrofurantetracarboxylicacid (7); the bis(trifluoromethyl) derivatives, exo-cis-2,4-bis(trifluoromethyl)-6,6,7,7-tetrafluoro-3-oxabicyclo [3.2.0]heptane (5) and exo-cis-2,4-bis(trifluoromethyl) -6,6,8,8-tetrafluoro-3,7-dioxabicyclo [3.3.0]heptane (8) are formed in lower or comparable amounts. (C) 1997 Elsevier Science S.A.