3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole | 919489-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole
• 英文别名: 3-(Pentadecafluoroheptyl)-5-(pentafluorophenyl)-1,2,4-oxadiazole；3-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoroheptyl)-5-(2,3,4,5,6-pentafluorophenyl)-1,2,4-oxadiazole
• CAS: 919489-99-9
• 化学式: C₁₅F₂₀N₂O
• 分子量: 604.146
• InChiKey: YROHNOYMVCOFGS-UHFFFAOYSA-N

物化性质

• 沸点：
  298.7±50.0 °C(Predicted)
• 密度：
  1.760±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole 在 potassium tert-butylate 、 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(2,3,5,6-tetrafluoro-4-(3-perfluoroheptyl-1,2,4-oxadiazol-5-yl)phenylamino)acetic acid
  参考文献：
  名称：

  Synthesis of fluorinated oxadiazoles with gelation and oxygen storage ability

  摘要：

  一种新的氟化低分子量（LMW）凝胶剂家族已经通过5-聚氟苯基-3-全氟庚基-1,2,4-噁二唑与甘氨酸酯的SNAr取代反应合成。所获得的化合物在DMSO中可形成热敏和pH敏感的水凝胶或热可逆的有机凝胶。氧溶解度研究表明其能够维持溶液和与平板计数琼脂（PCA）混合的凝胶中的高氧水平。

  DOI：

  10.1039/c2ob07024c
• 作为产物：
  描述：

  perfluorooctanoylamidooxime 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis of fluorinated oxadiazoles with gelation and oxygen storage ability

  摘要：

  一种新的氟化低分子量（LMW）凝胶剂家族已经通过5-聚氟苯基-3-全氟庚基-1,2,4-噁二唑与甘氨酸酯的SNAr取代反应合成。所获得的化合物在DMSO中可形成热敏和pH敏感的水凝胶或热可逆的有机凝胶。氧溶解度研究表明其能够维持溶液和与平板计数琼脂（PCA）混合的凝胶中的高氧水平。

  DOI：

  10.1039/c2ob07024c

文献信息

• Synthesis of fluorinated first generation starburst molecules containing a triethanolamine core and 1,2,4-oxadiazoles
  作者：Silvestre Buscemi、Andrea Pace、Antonio Palumbo Piccionello、Nicolò Vivona

  DOI：10.1016/j.jfluchem.2006.07.012

  日期：2006.12

  functionalize the aliphatic primary hydroxyl functionalities of triethanolamine, under mild conditions. UV–visible absorption and emission spectra are reported, for both tri- and difunctionalised molecules, showing their potential applications as light-emitters in optoelectronic devices.

  合成了5-五氟苯基-1，2，4-恶二唑在C（3）处不同的位置，并在温和条件下用于官能化三乙醇胺的脂肪族伯羟基官能团。报告了三官能和双官能分子的紫外可见吸收光谱和发射光谱，显示了它们在光电器件中作为发光体的潜在应用。
• Synthesis of a fluorinated graphene oxide–silica nanohybrid: improving oxygen affinity
  作者：A. Maio、D. Giallombardo、R. Scaffaro、A. Palumbo Piccionello、I. Pibiri

  DOI：10.1039/c6ra02585d

  日期：——

  modified method, the GO–silica nanohybrid (GOS) was obtained via Fischer esterification, the fluorinated moiety (3-pentadecafluoroheptyl-5-perfluorophenyl-1,2,4-oxadiazole) was introduced by nucleophilic substitution operated by the hydroxyl functionalities onto the GOS surface. Full characterization of the new materials confirmed the formation of covalent bonds between the graphene oxide/silica hybrid

  提出了一种简便的方法来实现氟化氧化石墨烯-二氧化硅纳米杂化物（GOSF）。用Hummer改进的方法合成了氧化石墨烯（GO）。费歇尔酯化反应中，通过羟基官能团操作的亲核取代作用将氟化部分（3-十五氟庚基-5-全氟苯基-1,2,4-恶二唑）引入GOS表面。新材料的全面表征证实了氧化石墨烯/二氧化硅杂化基质与氟化部分之间形成了共价键。所提出的方法提供了一种获得氟化碳/二氧化硅杂化纳米材料的简便方法，从而避免了通常在制备氟化材料时所涉及的苛刻反应条件，并允许选择性固定特定的氟尾。此外，进行的氧气吸收和释放动力学表明，氟化部分的引入增加了氧的交换，
• Fluorinated and pegylated polyaspartamide derivatives to increase solubility and efficacy of Flutamide
  作者：Antonio Palumbo Piccionello、Giovanna Pitarresi、Andrea Pace、Daniela Triolo、Pasquale Picone、Silvestre Buscemi、Gaetano Giammona

  DOI：10.3109/1061186x.2012.680961

  日期：2012.6

  New fluorinated amphiphilic copolymers based on a biocompatible polyaspartamide have been prepared in order to obtain polymeric micelles useful for delivering anticancer drugs. In particular, alpha,beta-poly(N-2-hydroxyethyl)-(D), (L)-aspartamide (PHEA) has been derivatized with polyethylene glycol (PEG(2000)) and ethylendiamine (EDA). Both these portions form the hydrophilic part of the copolymer, while the hydrophobic moiety is given by 1,2,4-oxadiazoles: 5-pentafluorophenyl-3-perfluoroheptyl-1,2,4-oxadiazole (PPOX) or 3-carboxyethyl-5-pentadecafluoroheptyl-1,2,4oxadiazole (CPOX). Copolymers named PHEA-PEG(2000)-EDA-PPOX and PHEA-PEG(2000)-EDA-CPOX have been prepared with various degrees of derivatization and characterized by spectroscopic analyses. Size exclusion chromatography, pyrene colorimetric assay, light scattering analysis and scanning electron microscopy have evidenced the occurrence of a self-association process in aqueous medium. The ability of these aggregates to incorporate a hydrophobic drug and increase its solubility has been evaluated by using Flutamide, a fluorinated anticancer agent. Moreover, the activity of Flutamide-loaded micelles on proliferation of dihydrotestosterone stimulated LNCaP cells has been determined and compared to that of free drug.
• Lower rim arylation of calix[n]arenes with extended perfluorinated domains
  作者：Silvestre Buscemi、Andrea Pace、Antonio Palumbo Piccionello、Sebastiano Pappalardo、Domenico Garozzo、Tullio Pilati、Giuseppe Gattuso、Andrea Pappalardo、Ilenia Pisagatti、Melchiorre F. Parisi

  DOI：10.1016/j.tetlet.2006.10.092

  日期：2006.12

  Exhaustive O-arylation of p-tert-butylcalix[n]arenes 2 (n = 4-8) with an excess of 3-pentadecafluoroheptyl-5-pentafluorophenyl-1,2,4-oxadiazole 3 and K2CO3 in refluxing acetonitrile provides an easy entry to a new family of perfluorinated calix[n]arenes 1. The cyclic tetramer furnishes a mixture of cone, partial cone, and 1,2-alternate conformers, while the larger macrocycles afford single products. The structures of all new compounds are substantiated by NMR techniques and MALDI-TOF mass spectral data. Single-crystal X-ray diffraction studies on the pentamer derivative 1b reveal a distorted cone-in conformation of the calixarene cup. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of fluorinated oxadiazoles with gelation and oxygen storage ability
  作者：Antonio Palumbo Piccionello、Annalisa Guarcello、Alessandro Calabrese、Ivana Pibiri、Andrea Pace、Silvestre Buscemi

  DOI：10.1039/c2ob07024c

  日期：——

  A new family of fluorinated low molecular weight (LMW) gelators has been synthesized through SNAr substitution of 5-polyfluoroaryl-3-perfluoroheptyl-1,2,4-oxadiazoles with glycine ester. The obtained compounds give thermal and pH-sensitive hydrogels or thermo-reversible organogels in DMSO. Oxygen solubility studies showed the ability to maintain high oxygen levels in solution and in gel blend with plate counter agar (PCA).

  一种新的氟化低分子量（LMW）凝胶剂家族已经通过5-聚氟苯基-3-全氟庚基-1,2,4-噁二唑与甘氨酸酯的SNAr取代反应合成。所获得的化合物在DMSO中可形成热敏和pH敏感的水凝胶或热可逆的有机凝胶。氧溶解度研究表明其能够维持溶液和与平板计数琼脂（PCA）混合的凝胶中的高氧水平。