decafluoro-1,3,5,7-tetrahydrobenzo<1,2-c:4,5-c'>difuran | 132757-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: decafluoro-1,3,5,7-tetrahydrobenzo<1,2-c:4,5-c'>difuran
• 英文别名: perfluoro-1,3,5,7-tetrahydrobenzo<1,2-c:4,5-c'>difuran；Perfluoro-1,3,5,7-tetrahydrobenzo[1,2-c:4,5-c']difuran；1,1,3,3,4,5,5,7,7,8-Decafluorofuro[3,4-f][2]benzofuran
• CAS: 132757-85-8
• 化学式: C₁₀F₁₀O₂
• 分子量: 342.093
• InChiKey: RRTJJBGORKPFMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  decafluoro-1,3,5,7-tetrahydrobenzo<1,2-c:4,5-c'>difuran 在 硫酸 作用下， 反应 5.0h， 以45.4%的产率得到difluoropyromellitic acid
  参考文献：
  名称：

  Reactions of tetrafluorophthalic and difluoropyromellitic acids with sulphur tetrafluoride

  摘要：

  Fluorination of tetrafluorophthalic acid (1) with an SF4/HF mixture at 190-300-degrees-C afforded, beside the expected perfluoro-o-xylene (2) and perfluoro-o-toluyl fluoride (4), considerable amounts of octafluoro-1,3-dihydroisobenzofuran (3). The reaction with difluoropyromellitic acid (5) at 190-degrees-C gave a mixture of perfluoro-2,4,5-trimethylbenzoyl fluoride (9), perfluoro-2,5-dimethylterephthaloyl difluoride (10a), perfluoro-2,4-dimethylisophthaloyl difluoride (10b) and perfluoro-5-methyl-6-fluoroformyl-1,3-dihydroisobenzofuran (11), but at 300-degrees-C perfluorodurene (6), perfluoro-5,6-dimethyl-1,3-dihydroisobenzofuran (7) and perfluoro-2,4,5-trimethylbenzoyl fluoride (9) were obtained in a 3:1:0.8 ratio.

  DOI：

  10.1016/s0022-1139(00)80039-1
• 作为产物：
  描述：

  dichloropyromellitic acid 在 potassium fluoride 、 sulfur tetrafluoride 、 氢氟酸 作用下， 以 环丁砜 为溶剂， 反应 21.0h， 生成 decafluoro-1,3,5,7-tetrahydrobenzo<1,2-c:4,5-c'>difuran
  参考文献：
  名称：

  多元卤代芳烃。第五部分。聚和全氟-1,3,5,7-四氢苯并[1,2-c：4,5-c']二呋喃的合成

  摘要：

  用四氟化硫和氟化氢的混合物处理二氯-或二溴均苯四甲酸1或2，分别得到4,8-二卤代-1,1,3,3,5,5,7,7-八氟-1,3， 5,7-四氢苯并[1,2-c：4,5-c']二呋喃（3）和（4）。二氯化合物3易于与氟化钾进行卤素交换，得到全氟-1,3,5,7-四氢苯并[1,2-c：4,5-c']二呋喃（5）。根据反应条件，用氢化铝锂还原二溴化合物4，得到1,1,3,3,5,5,5,7,7-八氟-1,3,5,7-四氢苯并[1,2- c：4,5-c']二呋喃（6）或4-溴-1,1,3,3,5,5,7,7-八氟-1,3,5,7-四氢苯并[1,2-c，4,5-c']二呋喃（7）。

  DOI：

  10.1016/s0022-1139(00)80312-7

文献信息

• Polyhaloaromatics. Part VI. The first synthesis of perfluorodurene
  作者：Wojciech Dmowski

  DOI：10.1016/0022-1139(93)02992-n

  日期：1994.7

  The final stages in preparation of pure perfluorodurene (3) are described. The synthesis involves cleavage of perfluoro-1,3,5,7-tetrahydrobenzo[1,2-c:4,5-c']difuran (1) with SbF5 and anhydrous HF and treatment of the resulting mixture of perfluoro-2,5-dimethylterephthaloyl difluoride (2a) and perfluoro-2,4-dimethylisophthaloyl difluoride (2b) with SF4 and HF at 300–330 °C. Compound 3 has been characterised

  描述了制备纯全氟二烯（3）的最后阶段。合成涉及用SbF 5和无水HF裂解全氟1,3,5,7-四氢苯并[1,2- c：4,5- c ']二呋喃（1）并处理所得的全氟2混合物1,5-二甲基对苯二甲酰氟（2a）和2,4-二甲基间苯二甲酰氟（2b），SF 4和HF在300–330°C下。化合物3已通过元素分析，19 F和13 C NMR光谱法和质谱法表征。
• The chemistry of perhalo-1,3,5,7-tetrahydrobenzo-[1,2-c:4,5-c′]-difuran: unusually stable solid state complexes with tertiary amides
  作者：Halina Plenkiewicz、Zofia Urbańczyk-Lipkowska、Wojciech Dmowski

  DOI：10.1016/s0022-1139(99)00304-8

  日期：2000.4

  The base catalyzed reactions of perfluoro-1,3,5,7-tetrahydrobenzo[1,2-c;4,5-c']difuran (I) and 4,8-dichloro-perfluoro-1,3,5,7-tetrahydrobenzo[l,2-c;4,5-c']difuran (3) with tertiary amides gave chemically and thermally stable crystalline complexes 2a-e and 4a-d, respectively. The X-ray structure determination of 2c has shown the shortest known intermolecular C=O...phenol H-bonding distance and the shortest C=O...F non-bonding interaction. (C) 2000 Elsevier Science S.A. All rights reserved.
• Reactions of tetrafluorophthalic and difluoropyromellitic acids with sulphur tetrafluoride
  作者：Wojciech Dmowski

  DOI：10.1016/s0022-1139(00)80039-1

  日期：1993.2

  Fluorination of tetrafluorophthalic acid (1) with an SF4/HF mixture at 190-300-degrees-C afforded, beside the expected perfluoro-o-xylene (2) and perfluoro-o-toluyl fluoride (4), considerable amounts of octafluoro-1,3-dihydroisobenzofuran (3). The reaction with difluoropyromellitic acid (5) at 190-degrees-C gave a mixture of perfluoro-2,4,5-trimethylbenzoyl fluoride (9), perfluoro-2,5-dimethylterephthaloyl difluoride (10a), perfluoro-2,4-dimethylisophthaloyl difluoride (10b) and perfluoro-5-methyl-6-fluoroformyl-1,3-dihydroisobenzofuran (11), but at 300-degrees-C perfluorodurene (6), perfluoro-5,6-dimethyl-1,3-dihydroisobenzofuran (7) and perfluoro-2,4,5-trimethylbenzoyl fluoride (9) were obtained in a 3:1:0.8 ratio.
• Polyhaloaromatics. Part V. Synthesis of poly- and perfluoro-1,3,5,7-tetrahydrobenzo[1,2-c:4,5-c′] difurans
  作者：Jacek Porwisiak、Wojciech Dmowski

  DOI：10.1016/s0022-1139(00)80312-7

  日期：1991.1

  Treatment of dichloro- or dibromopyromellitic acids 1 or 2 with a mixture of sulphur tetrafluoride and hydrogen fluoride gave the respective 4,8-dihalo-1,1,3,3,5,5,7,7-octafluoro-1,3,5,7-tetrahydrobenzo[1,2-c:4,5-c′]difurans (3) and (4) in high yields. Dichloro compound 3 easily undergoes halogen-exchange with potassium fluoride to give perfluoro-1,3,5,7-tetrahydrobenzo[1,2-c:4,5-c′]difuran (5). Reduction

  用四氟化硫和氟化氢的混合物处理二氯-或二溴均苯四甲酸1或2，分别得到4,8-二卤代-1,1,3,3,5,5,7,7-八氟-1,3， 5,7-四氢苯并[1,2-c：4,5-c']二呋喃（3）和（4）。二氯化合物3易于与氟化钾进行卤素交换，得到全氟-1,3,5,7-四氢苯并[1,2-c：4,5-c']二呋喃（5）。根据反应条件，用氢化铝锂还原二溴化合物4，得到1,1,3,3,5,5,5,7,7-八氟-1,3,5,7-四氢苯并[1,2- c：4,5-c']二呋喃（6）或4-溴-1,1,3,3,5,5,7,7-八氟-1,3,5,7-四氢苯并[1,2-c，4,5-c']二呋喃（7）。