3-fluoro-4-(hydroxymethyl)phenoxyacetic acid | 214554-36-6

• 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: 3-fluoro-4-(hydroxymethyl)phenoxyacetic acid
• 英文别名: 2-[3-Fluoro-4-(hydroxymethyl)phenoxy]acetic acid
• CAS: 214554-36-6
• 化学式: C₉H₉FO₄
• 分子量: 200.166
• InChiKey: RMKDKDYDHYJVQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  五氟苯酚 、 3-fluoro-4-(hydroxymethyl)phenoxyacetic acid 在 N,N'-二异丙基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (3-Fluoro-4-hydroxymethyl-phenoxy)-acetic acid pentafluorophenyl ester
  参考文献：
  名称：

  固相有机合成中常用树脂的凝胶相19F NMR光谱质量；肽固相糖基化的研究。

  摘要：

  通过（19）F NMR光谱研究了固相合成中使用的七种不同商业树脂的光谱性质。在每种树脂上合成了一个氟标记的二肽，并用a来测量CDCl（3），DMSO-d（6），苯-d（6）和CD（3）OD中（19）F共振的分辨率。传统的NMR光谱仪，即不使用魔角旋转。通常，发现含有聚乙二醇链的树脂（ArgoGel，TentaGel和PEGA）有利于（19）F NMR光谱质量。然后在用氟标记的接头官能化的ArgoGel树脂上制备三个含丝氨酸的三肽，五肽和七肽。利用带有氟标记的保护基的硫代半乳糖苷糖基供体对树脂结合的肽进行糖基化。用凝胶相（19）F NMR光谱监测糖基化可以使用最少量的糖基供体（3 x 2当量）以相似的80％收率形成每个糖肽。另外，发现糖基化产率与肽长度无关。

  DOI：

  10.1039/b404802d
• 作为产物：
  描述：

  3-氟-4-(羟基甲基)苯酚 在 lithium hydroxide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 生成 3-fluoro-4-(hydroxymethyl)phenoxyacetic acid
  参考文献：
  名称：

  Fluorinated linkers for monitoring solid-phase synthesis using gel-phase 19F NMR spectroscopy

  摘要：

  Three fluorinated linkers which are analogues of linkers commonly used in solid-phase peptide synthesis have been prepared. Using F-19 NMR spectroscopy, the fluorine atom of the linker allowed monitoring of several transformations in the solid-phase synthesis of a peptoid having a coumarin moiety. Especially, attachment of the linker to the solid phase, coupling of the first building block to the linker and cleavage of the product were efficiently monitored and optimised. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01541-x

文献信息

• [EN] COMPOUNDS DIRECTED AGAINST PILUS BIOGENESIS AND ACTIVITY IN PATHOGENIC BACTERIA; METHODS AND COMPOSITIONS FOR SYNTHESIS THEREOF<br/>[FR] COMPOSES DIRIGES CONTRE LA BIOGENESE ET L'ACTIVITE DU PILUS DE BACTERIES PATHOGENES, ET PROCEDES ET COMPOSITIONS DE SYNTHESE DESTINES A CES COMPOSES
  申请人：UNIV WASHINGTON

  公开号：WO2001020995A1

  公开（公告）日：2001-03-29

  Many Gram-negative pathogens assemble adhesive structures on their surfaces that allow them to colonize host tissues and cause disease. Novel compositions which inhibit or prevent the formation of a pilus chaperone-subunit complex are disclosed. Interfering with the function of the pili chaperone negatively affects the chaperone/usher pathway which is one molecular mechanism by which Gram-negative bacteria assemble adhesive pili structures and thus prevent or inhibit pilus assembly. Also provided are methods for the treatment or prevention of diseases caused by tissue-adhering pilus-forming bacteria by inhibiting the function of pilus chaperones. Also provided are pharmaceutical preparations capable of inhibiting or preventing the formation of a pilus chaperone-subunit complex. Also provided are methods of synthesizing the N-substituted amino acid compounds and compounds useful for the synthesis thereof. In particular, novel fluorinated linker compounds and methods of synthesis are provided. Methods for using the fluorinated linker compounds in methods of solid-phase synthesis of the N-substituted amino acid compounds are also disclosed.
• Fluorinated linkers for monitoring solid-phase synthesis using gel-phase 19F NMR spectroscopy
  作者：Anette Svensson、Karl-Erik Bergquist、Tomas Fex、Jan Kihlberg

  DOI：10.1016/s0040-4039(98)01541-x

  日期：1998.9

  Three fluorinated linkers which are analogues of linkers commonly used in solid-phase peptide synthesis have been prepared. Using F-19 NMR spectroscopy, the fluorine atom of the linker allowed monitoring of several transformations in the solid-phase synthesis of a peptoid having a coumarin moiety. Especially, attachment of the linker to the solid phase, coupling of the first building block to the linker and cleavage of the product were efficiently monitored and optimised. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Gel-phase¹⁹F NMR spectral quality for resins commonly used in solid-phase organic synthesis; a study of peptide solid-phase glycosylations
  作者：Mickael Mogemark、Frida Gårdmo、Tobias Tengel、Jan Kihlberg、Mikael Elofsson

  DOI：10.1039/b404802d

  日期：——

  spectroscopic properties for seven different commercial resins used in solid-phase synthesis were investigated with (19)F NMR spectroscopy. A fluorine-labeled dipeptide was synthesized on each resin, and the resolution of the (19)F resonances in CDCl(3), DMSO-d(6), benzene-d(6) and CD(3)OD were measured with a conventional NMR spectrometer, i.e. without using magic angle spinning. In general, resins

  通过（19）F NMR光谱研究了固相合成中使用的七种不同商业树脂的光谱性质。在每种树脂上合成了一个氟标记的二肽，并用a来测量CDCl（3），DMSO-d（6），苯-d（6）和CD（3）OD中（19）F共振的分辨率。传统的NMR光谱仪，即不使用魔角旋转。通常，发现含有聚乙二醇链的树脂（ArgoGel，TentaGel和PEGA）有利于（19）F NMR光谱质量。然后在用氟标记的接头官能化的ArgoGel树脂上制备三个含丝氨酸的三肽，五肽和七肽。利用带有氟标记的保护基的硫代半乳糖苷糖基供体对树脂结合的肽进行糖基化。用凝胶相（19）F NMR光谱监测糖基化可以使用最少量的糖基供体（3 x 2当量）以相似的80％收率形成每个糖肽。另外，发现糖基化产率与肽长度无关。