4-(3-(trifluoromethyl)diaziridin-3-yl)benzoic acid tert-butyl ester | 1210908-12-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 4-(3-(trifluoromethyl)diaziridin-3-yl)benzoic acid tert-butyl ester
• CAS: 1210908-12-5
• 化学式: C₁₃H₁₅F₃N₂O₂
• 分子量: 288.27
• InChiKey: PQHOBQDUALRFSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70.18
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(3-(trifluoromethyl)diaziridin-3-yl)benzoic acid tert-butyl ester 在 silver(l) oxide 作用下， 反应 3.0h， 生成 4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzoic acid tert-butyl ester
  参考文献：
  名称：

  Comparing Lipid Photo-Cross-linking Efficacy of Penetratin Analogues Bearing Three Different Photoprobes: Dithienyl Ketone, Benzophenone, and Trifluoromethylaryldiazirine

  摘要：

  Photoactivatable penetratin analogues bearing three different photoprobes, which do not disturb the membranotropic properties of the peptides, have been tested for their photo-cross-linking efficacy in glycerol and lipid media. In the case of glycerol, photo-cross-linking was observed, whereas in the case of SDS (used as a membrane model system), the dynamics of the SDS/penetratin assemblies and the photosensitizer properties of the probes prevented the cross-linking between the peptide and SDS. Bilayers of DMPG were partially photo-cross-linked by the penetratin analogues containing either a benzophenone or a trifluoromethylaryl-diazirine, whereas dithienyl ketone acted exclusively as a photosensitizer. The characterization by MALDI-TOF mass spectrometry of the photoadducts formed alter irradiation required basic hydrolysis of DMPG for an efficient capture of the biotinylated peptide analogues with streptavidin-coated magnetic beads. MALDI-TOF analysis of the photoadducts between the photoactivatable penetratin and DMPG allowed an unambiguous identification of the covalent bond formed with the lipids. Altogether, we show herein that the efficacy of the lipid photo-cross-linking depends on the environment, the dynamics of the supramolecular assembly, and the physicochemical properties of the photoprobe.

  DOI：

  10.1021/bc900466q
• 作为产物：
  描述：

  4-(2,2,2-trifluoro-1-((p-tolylsulfonyloxy)imino)ethyl)benzoic acid tert-butyl ester 在 氨 作用下， 反应 48.25h， 以88%的产率得到4-(3-(trifluoromethyl)diaziridin-3-yl)benzoic acid tert-butyl ester
  参考文献：
  名称：

  Comparing Lipid Photo-Cross-linking Efficacy of Penetratin Analogues Bearing Three Different Photoprobes: Dithienyl Ketone, Benzophenone, and Trifluoromethylaryldiazirine

  摘要：

  Photoactivatable penetratin analogues bearing three different photoprobes, which do not disturb the membranotropic properties of the peptides, have been tested for their photo-cross-linking efficacy in glycerol and lipid media. In the case of glycerol, photo-cross-linking was observed, whereas in the case of SDS (used as a membrane model system), the dynamics of the SDS/penetratin assemblies and the photosensitizer properties of the probes prevented the cross-linking between the peptide and SDS. Bilayers of DMPG were partially photo-cross-linked by the penetratin analogues containing either a benzophenone or a trifluoromethylaryl-diazirine, whereas dithienyl ketone acted exclusively as a photosensitizer. The characterization by MALDI-TOF mass spectrometry of the photoadducts formed alter irradiation required basic hydrolysis of DMPG for an efficient capture of the biotinylated peptide analogues with streptavidin-coated magnetic beads. MALDI-TOF analysis of the photoadducts between the photoactivatable penetratin and DMPG allowed an unambiguous identification of the covalent bond formed with the lipids. Altogether, we show herein that the efficacy of the lipid photo-cross-linking depends on the environment, the dynamics of the supramolecular assembly, and the physicochemical properties of the photoprobe.

  DOI：

  10.1021/bc900466q

文献信息

• Alternative One-Pot Synthesis of (Trifluoromethyl)phenyldiazirines from Tosyloxime Derivatives: Application for New Synthesis of Optically Pure Diazirinylphenylalanines for Photoaffinity Labeling
  作者：Lei Wang、Yuta Murai、Takuma Yoshida、Akiko Ishida、Katsuyoshi Masuda、Yasuko Sakihama、Yasuyuki Hashidoko、Yasumaru Hatanaka、Makoto Hashimoto

  DOI：10.1021/ol503630z

  日期：2015.2.6

  Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2– is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.

  开发了由相应的甲苯磺肟肟形成的另一种一锅法合成3-（三氟甲基）-3-苯基重氮基衍生物。中间diaziridine的由NH去质子化2 -是用于施工二吖丙因的新方法。而且，尝试了涉及这些方法的光学纯的（三氟甲基）二氮杂基苯基丙氨酸衍生物的新型合成。