ethyl 5-(perfluoroheptyl)-3H-1,2,3-triazole-4-carboxylate | 150758-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 5-(perfluoroheptyl)-3H-1,2,3-triazole-4-carboxylate
• 英文别名: ethyl 5-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoroheptyl)-2H-triazole-4-carboxylate
• CAS: 150758-90-0
• 化学式: C₁₂H₆F₁₅N₃O₂
• 分子量: 509.175
• InChiKey: IPARWMTVNOBFKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  ethyl 5-(perfluoroheptyl)-3H-1,2,3-triazole-4-carboxylate 在 sodium hydroxide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以95%的产率得到5-(perfluoroheptyl)-3H-1,2,3-triazole-4-carboxylic acid
  参考文献：
  名称：

  F-两亲性 1,2,3-三唑通过乙烯基叠氮化物的意外分子内环化

  摘要：

  通过带有吸电子基团的乙烯基叠氮化物的出人意料的分子内环化，已经以显着的产率合成了一系列氟烷基化的 1,2,3-三唑。本研究中提出的机制意味着催化量的叠氮离子参与乙烯基叠氮化物环化为三唑。该研究包括用各种烷化剂对这些化合物进行烷基化，并评估离子衍生物的表面活性。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008 年）

  DOI：

  10.1002/ejoc.200700924
• 作为产物：
  描述：

  Ethyl 3-F-heptyl propynoate 在 甲醇 、 叠氮基三甲基硅烷 作用下， 以 乙醚 为溶剂， 反应 29.0h， 以95%的产率得到ethyl 5-(perfluoroheptyl)-3H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  Synthese et reactivite de nouveaux synthons perfluoroalkyles. comportement atypique des azirines et aziridines F-alkylees.

  摘要：

  F-alkyl chains perturb the reactivity of substrates in an often unpredictable way. F-alkyl azirine and aziridine carboxylates were prepared from F-alkynylesters, in 80 and 60% yield, respectively, and were found to display reactivities different from those of their hydrocarbon analogs. Thus, F-alkylazirines (5) give addition products easily but resist ring opening, while the F-alkylaziridines (8) are extremely stable, both towards nucleophilic and electrophilic reagents and irrespective of the medium used, neutral, acid or basic.

  DOI：

  10.1016/s0040-4020(01)81291-6

文献信息

• F-Amphiphilic 1,2,3-Triazoles by Unexpected Intramolecular Cyclisation of Vinyl Azides
  作者：Estelle Mayot、Pascal Lemière、Christine Gérardin-Charbonnier

  DOI：10.1002/ejoc.200700924

  日期：2008.5

  A series of fluoroalkylated 1,2,3-triazoles have been synthetised in significant yields through unexpected intramolecular cyclisations of vinyl azides bearing electron-withdrawing groups. The mechanism proposed in this study implies the participation of a catalytic amount of azide ions in the cyclisations of the vinyl azides to triazoles. The study includes the alkylation of these compounds with various

  通过带有吸电子基团的乙烯基叠氮化物的出人意料的分子内环化，已经以显着的产率合成了一系列氟烷基化的 1,2,3-三唑。本研究中提出的机制意味着催化量的叠氮离子参与乙烯基叠氮化物环化为三唑。该研究包括用各种烷化剂对这些化合物进行烷基化，并评估离子衍生物的表面活性。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008 年）
• Synthese et reactivite de nouveaux synthons perfluoroalkyles. comportement atypique des azirines et aziridines F-alkylees.
  作者：Mustapha Haddach、Raphaël Pastor、Jean G. Riess

  DOI：10.1016/s0040-4020(01)81291-6

  日期：1993.5

  F-alkyl chains perturb the reactivity of substrates in an often unpredictable way. F-alkyl azirine and aziridine carboxylates were prepared from F-alkynylesters, in 80 and 60% yield, respectively, and were found to display reactivities different from those of their hydrocarbon analogs. Thus, F-alkylazirines (5) give addition products easily but resist ring opening, while the F-alkylaziridines (8) are extremely stable, both towards nucleophilic and electrophilic reagents and irrespective of the medium used, neutral, acid or basic.
• Proton conductivity properties of acid doped fluoroalkylated 1,2,3-triazole
  作者：Sedat Coşgun、Sevim Ünügür Çelik、Şehmus Özden、Suat Tüysüz、Ayhan Bozkurt、Christine Gérardin-Charbonnier

  DOI：10.1016/j.jfluchem.2010.03.015

  日期：2010.7

  Novel proton conducting organic electrolyte containing fluoroalkylated 1,2,3-triazole was synthesized via intramolecular cyclisation of vinyl azides. FT-IR, elemental analysis and NMR methods were used for the characterization of the resulting organic molecule. Triazole containing sample was doped with triflic acid to obtain proton conducting organic electrolytes. Thermal stability of these materials was analyzed with thermogravimetric analysis (TGA) and the melting temperatures were measured by differential scanning calorimetry (DSC). The effect of acid content on the proton conductivity was investigated with impedance spectrometer and the maximum proton conductivity was measured as 10(-2) S/cm at 150 degrees C. (C) 2010 Elsevier B.V. All rights reserved.