4-perfluorooctylbenzaldehyde | 134641-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-perfluorooctylbenzaldehyde
• 英文别名: 4-(Heptadecafluorooctyl)benzaldehyde；4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)benzaldehyde
• CAS: 134641-35-3
• 化学式: C₁₅H₅F₁₇O
• 分子量: 524.177
• InChiKey: FZVSQOKOTWICAY-UHFFFAOYSA-N

物化性质

• 沸点：
  276.2±40.0 °C(Predicted)
• 密度：
  1.604±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  吡咯 、 4-perfluorooctylbenzaldehyde 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 5,10,15,20-tetrakis-(4-perfluorooctylphenyl)porphyrin
  参考文献：
  名称：

  Epoxidation of Alkenes Under Liquid-Liquid Biphasic Conditions: Synthesis and Catalytic Activity of Mn(III)-Tetraarylporphyrins Bearing Perfluoroalkyl Tails.

  摘要：

  Four tetraarylporphyrins bearing one n-C8F17 chain on each meso-aryl group have been synthesized. The Mn(III)-complexes of these new compounds (Mn-1 - Mn-4) were used as catalysts in alkene epoxidations carried out under aqueous-organic biphasic conditions. High epoxide yields were obtained with catalysts in which, along with perfluoroalkyl chains, bulky substituents were present at appropriate positions. The expected general enhancement of stability and catalytic activity due to the electron-withdrawing effect of n-C8F17 substituents was not observed. However, Mn-4 was found to be an exceptionally active catalyst for NaOCl promoted epoxidation of poorly reactive linear alpha-alkenes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00272-x
• 作为产物：
  描述：

  methyl 4-perfluorooctylbenzoate 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 10.0h， 生成 4-perfluorooctylbenzaldehyde
  参考文献：
  名称：

  Epoxidation of Alkenes Under Liquid-Liquid Biphasic Conditions: Synthesis and Catalytic Activity of Mn(III)-Tetraarylporphyrins Bearing Perfluoroalkyl Tails.

  摘要：

  Four tetraarylporphyrins bearing one n-C8F17 chain on each meso-aryl group have been synthesized. The Mn(III)-complexes of these new compounds (Mn-1 - Mn-4) were used as catalysts in alkene epoxidations carried out under aqueous-organic biphasic conditions. High epoxide yields were obtained with catalysts in which, along with perfluoroalkyl chains, bulky substituents were present at appropriate positions. The expected general enhancement of stability and catalytic activity due to the electron-withdrawing effect of n-C8F17 substituents was not observed. However, Mn-4 was found to be an exceptionally active catalyst for NaOCl promoted epoxidation of poorly reactive linear alpha-alkenes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00272-x

文献信息

• The synthesis of perfluoroalkyl and perfluoroalkylether substituted benzils
  作者：K.J.L. Paciorek、S.R. Masuda、J.G. Shih、J.H. Nakahara

  DOI：10.1016/s0022-1139(00)82343-x

  日期：1991.7

  C8F17C6H4CHO, C8F17C6H4CO2H, C8F17C6H4COCOC6H5, and C8F17OCF2CF2C6H4COCOC6H5 proceeded readily. No C8F17OCF2C6H4COCOC6H5 was produced from the reaction of C8F17OCF2I with 4-iodobenzil in the presence of copper bronze. Low yields of bridged bisbenzils were obtained from the coupling reactions of ICF2CF2O(CF2)5OCF2CF2I and I(CF2CF2O)5CF2CF2I with 4-iodobenzil. Based on by-products formed, the operative

  合成了单-和二-碘全氟烷基醚，并研究了它们与碘氟烷烃与4-碘联苯胺的反应。C 8 F 17 C 6 H 4 CHO，C 8 F 17 C 6 H 4 CO 2 H，C 8 F 17 C 6 H 4 COCOC 6 H 5和C 8 F 17 OCF 2 CF 2 C 6 H的形成4可可6 H 5进行得很顺利。在铜青铜的存在下，由C 8 F 17 OCF 2 I与4-碘代苯甲腈的反应没有产生C 8 F 17 OCF 2 C 6 H 4 COCOC 6 H 5。从ICF 2 CF 2 O（CF 2）5 OCF 2 CF 2 I和I（CF 2 CF 2 O）5 CF 2 CF 2的偶联反应中获得低产率的桥联联苯。我用4-碘苯苄。根据形成的副产物，推测其作用机理。
• Perfluoroalkyl migration in the rearrangement of 4-perfluoroalkyl-4-quinols
  作者：Hidemitsu Uno、Ayumi Yayama、Hitomi Suzuki

  DOI：10.1016/s0040-4020(01)86584-4

  日期：1992.9

  Heating a DMSO solution of 4-(perfluoro-n-alkyl)-4-hydroxy-2,5-cyclohexadien-1-one (4-perfluoroalkyl-4-quinols) in the presence of a catalytic amount of base brought about 1,2-migration of the perfluoroalkyl group to give 2-(perfluoro-n-alkyl)hydroquinone or 5-(perfluoro-n-alkyl)-2-cyclohexene-1,4-dione depending upon the substitution pattern of the quinol. The similar rearrangement of 4-perfluoroisopropyl-4-hydroxy-2,5-cyclohexadien-1-one occurred very smoothly at room temperature under the basic conditions. 5-Hydroxy-4-methyl-5-perfluorooctyl-1-propyl-3-pyrrolin-2-one underwent the base-induced rearrangement to afford a perfluorooctylated succinimide derivative. On the other hand, 5-hydroxy-3-methyl-5-perfluorooctyl-1-propyl-3-pyrrolin-2-one and 5-hydroxy-1-isobutyl-5-perfluorooctyl-3-pyrrolin-2-one did not suffer any rearrangement, although their structures were very similar to the 4-methylated one.
• Buckminsterfullerene derivatives bearing a fluoroalkyl group for use in organic photovoltaic cells
  作者：Makoto Karakawa、Takabumi Nagai、Tomomi Irita、Kenji Adachi、Yutaka Ie、Yoshio Aso

  DOI：10.1016/j.jfluchem.2012.09.009

  日期：2012.12

  Six novel fluoroalkylpyrrolidine-substituted [60]fullerene derivatives were synthesized and their ability to perform as new n-type organic photovoltaic materials was evaluated. The fullerene derivatives were soluble in common organic solvents, affording good processability properties for the fabrication of photovoltaic cells, and showed an absorption range and molar extinctions similar to those of 16,6]-phenyl C-61 butyric acid methyl ester. Bulk-heterojunction photovoltaic cells using poly(3-hexylthiophene):fullerene derivative blends as the photovoltaic active layers were fabricated and characterized. The performances of the photovoltaic cells were notably affected by the substituents on the fullerene derivatives. Short fluoroalkyl (C4F9) chains on pyrrolidine-linked phenyl groups were suitable substituents for the photovoltaic materials in the current study. This fullerene derivative bearing a C4F9-phenyl group showed a moderate power conversion efficiency of 0.53% during simulated AM 1.5 G solar irradiation at 100 mW/cm(2). This is so far the first report of the use of fluoroalkyl fullerene derivatives as the active materials in organic photovoltaic cells. (C) 2012 Elsevier B.V. All rights reserved.