2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-octanedial | 148291-67-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-octanedial
• 英文别名: 2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluorooctanedial
• CAS: 148291-67-2
• 化学式: C₈H₂F₁₂O₂
• 分子量: 358.084
• InChiKey: FHIGVZGPRIQVEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-octanedial 、 甲基-Alpha-D-吡喃鼠李糖苷 在 2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-octanedial 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以18%的产率得到methyl 2,3-O-carbonyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents Part 17: Sonochemical-forced preparation of perfluoroalkanals and their use for non-conventional acetalations of carbohydrates

  摘要：

  The homologous 1-iodo-perfluoroalkanes 1a-1c and alpha,omega-dibromo-perfluoroalkanes 4a, 4b were carbonylated with DMF in the presence of Al/SnCl2 or Al/PbBr2 under sonication in a short reaction time. The hydrated aldehydes 2a-2c and 5a, 5b respectively were obtained in good yields allowing dehydration to 3a-3c and 6a, 6b. Some of the fluorinated aldehydes were selected as substrates in a Wittig-Homer olefination assisted by ultrasound and in non-conventional acetalations of methyl alpha-L-rhamnopyranoside (9). Thus, (E)-1-perfluorooctyl-2-phenylsulphonyl-ethene (8) was prepared from 3c and the phosphonate 7 by Wittig-Horner synthesis. Acetalations of 9 were carried out with the aldehydes (3a, 3b, 6a), hydrated aldehydes (2a, 2b), and the aldehyde hemiacetal 12 respectively, in the presence of dicyclohexylcarbodiimide (DCC). In all cases, a selective epimerization was observed at the C-atom 3 of the monosaccharide, i.e. polyfluoroalkylidenated 6-deoxy-alpha-L-altropyranosides 10, 11, 13, and 14 were obtained. (C) 1997 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(96)03551-8
• 作为产物：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-octane-1,1,8,8-tetraol 在 phosphorus pentoxide 作用下， 生成 2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-octanedial
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents Part 17: Sonochemical-forced preparation of perfluoroalkanals and their use for non-conventional acetalations of carbohydrates

  摘要：

  The homologous 1-iodo-perfluoroalkanes 1a-1c and alpha,omega-dibromo-perfluoroalkanes 4a, 4b were carbonylated with DMF in the presence of Al/SnCl2 or Al/PbBr2 under sonication in a short reaction time. The hydrated aldehydes 2a-2c and 5a, 5b respectively were obtained in good yields allowing dehydration to 3a-3c and 6a, 6b. Some of the fluorinated aldehydes were selected as substrates in a Wittig-Homer olefination assisted by ultrasound and in non-conventional acetalations of methyl alpha-L-rhamnopyranoside (9). Thus, (E)-1-perfluorooctyl-2-phenylsulphonyl-ethene (8) was prepared from 3c and the phosphonate 7 by Wittig-Horner synthesis. Acetalations of 9 were carried out with the aldehydes (3a, 3b, 6a), hydrated aldehydes (2a, 2b), and the aldehyde hemiacetal 12 respectively, in the presence of dicyclohexylcarbodiimide (DCC). In all cases, a selective epimerization was observed at the C-atom 3 of the monosaccharide, i.e. polyfluoroalkylidenated 6-deoxy-alpha-L-altropyranosides 10, 11, 13, and 14 were obtained. (C) 1997 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(96)03551-8
• 作为试剂：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-octanedial 、 甲基-Alpha-D-吡喃鼠李糖苷 在 2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluoro-octanedial 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以18%的产率得到methyl 2,3-O-carbonyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents Part 17: Sonochemical-forced preparation of perfluoroalkanals and their use for non-conventional acetalations of carbohydrates

  摘要：

  The homologous 1-iodo-perfluoroalkanes 1a-1c and alpha,omega-dibromo-perfluoroalkanes 4a, 4b were carbonylated with DMF in the presence of Al/SnCl2 or Al/PbBr2 under sonication in a short reaction time. The hydrated aldehydes 2a-2c and 5a, 5b respectively were obtained in good yields allowing dehydration to 3a-3c and 6a, 6b. Some of the fluorinated aldehydes were selected as substrates in a Wittig-Homer olefination assisted by ultrasound and in non-conventional acetalations of methyl alpha-L-rhamnopyranoside (9). Thus, (E)-1-perfluorooctyl-2-phenylsulphonyl-ethene (8) was prepared from 3c and the phosphonate 7 by Wittig-Horner synthesis. Acetalations of 9 were carried out with the aldehydes (3a, 3b, 6a), hydrated aldehydes (2a, 2b), and the aldehyde hemiacetal 12 respectively, in the presence of dicyclohexylcarbodiimide (DCC). In all cases, a selective epimerization was observed at the C-atom 3 of the monosaccharide, i.e. polyfluoroalkylidenated 6-deoxy-alpha-L-altropyranosides 10, 11, 13, and 14 were obtained. (C) 1997 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(96)03551-8

文献信息

• A novel synthesis of per(poly)fluoroalkyl aldehydes
  作者：Chang-Ming Hu、Xiao-Qing Tang

  DOI：10.1016/s0022-1139(00)80105-0

  日期：1993.4

  A novel synthesis of per(poly)fluoroalkyl aldehydes in high yield by the reaction ofper(poly)fluoroalkyl iodides or bromides with dimethylformamide initiated by aPbBr2(catalyst)/Al bimetal redox system is described.

  通过由PbBr 2（催化剂）/ Al双金属氧化还原体系引发的全（多）氟烷基碘或溴化物与二甲基甲酰胺的反应，高产率地合成全（多）氟烷基醛。
• Organofluorine compounds and fluorinating agents Part 17: Sonochemical-forced preparation of perfluoroalkanals and their use for non-conventional acetalations of carbohydrates
  作者：Alexey O. Miller、Dietmar Peters、Cornelia Zur、Michael Frank、Ralf Miethchen

  DOI：10.1016/s0022-1139(96)03551-8

  日期：1997.4

  The homologous 1-iodo-perfluoroalkanes 1a-1c and alpha,omega-dibromo-perfluoroalkanes 4a, 4b were carbonylated with DMF in the presence of Al/SnCl2 or Al/PbBr2 under sonication in a short reaction time. The hydrated aldehydes 2a-2c and 5a, 5b respectively were obtained in good yields allowing dehydration to 3a-3c and 6a, 6b. Some of the fluorinated aldehydes were selected as substrates in a Wittig-Homer olefination assisted by ultrasound and in non-conventional acetalations of methyl alpha-L-rhamnopyranoside (9). Thus, (E)-1-perfluorooctyl-2-phenylsulphonyl-ethene (8) was prepared from 3c and the phosphonate 7 by Wittig-Horner synthesis. Acetalations of 9 were carried out with the aldehydes (3a, 3b, 6a), hydrated aldehydes (2a, 2b), and the aldehyde hemiacetal 12 respectively, in the presence of dicyclohexylcarbodiimide (DCC). In all cases, a selective epimerization was observed at the C-atom 3 of the monosaccharide, i.e. polyfluoroalkylidenated 6-deoxy-alpha-L-altropyranosides 10, 11, 13, and 14 were obtained. (C) 1997 Elsevier Science S.A. All rights reserved.