3-氟-4-(羟甲基)苯甲酸 | 214554-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氟-4-(羟甲基)苯甲酸
• 英文名称: 3-fluoro-4-(hydroxymethyl)benzoic Acid
• CAS: 214554-16-2
• 化学式: C₈H₇FO₃
• mdl: MFCD15202208
• 分子量: 170.14
• InChiKey: HPVLUHTXWWJJHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氟-4-(羟甲基)苯甲酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以89 %的产率得到
  参考文献：
  名称：

  Controlled Self‐Assembly of Discrete Amphiphilic Oligourethanes with a Cascade Self‐Immolative Motif

  摘要：

  摘要 离散聚合物为理解精确的链结构、独特的自组装行为和功能应用之间的相互作用提供了一个极好的平台，而具有自惰性的离散聚合物的开发仍然很少。在这里，我们通过迭代逐步生长的方法，模块化合成了含有 N-萘基氨基甲酸酯或 N-（3-氟苯基）氨基甲酸酯重复单元的离散自褪色低聚氨基甲酸酯库。这些低聚氨基甲酸酯不仅会通过光介导的邻硝基氨基甲酸苄酯触发器的去除而发生级联 1,6- 消除解聚，而且在 MS/MS 条件下，即使没有紫外光照射，也会发生苄基-O 链接的选择性裂解。在水介质中，这些离散的低聚氨基甲酸乙酯会根据链长和骨架成分的不同自组装成不同的形态，如扁平纳米片、纳米纤维和纳米带。

  DOI：

  10.1002/anie.202306119
• 作为产物：
  描述：

  3-氟-4-甲酰基苯甲酸 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 生成 3-氟-4-(羟甲基)苯甲酸
  参考文献：
  名称：

  Controlled Self‐Assembly of Discrete Amphiphilic Oligourethanes with a Cascade Self‐Immolative Motif

  摘要：

  摘要 离散聚合物为理解精确的链结构、独特的自组装行为和功能应用之间的相互作用提供了一个极好的平台，而具有自惰性的离散聚合物的开发仍然很少。在这里，我们通过迭代逐步生长的方法，模块化合成了含有 N-萘基氨基甲酸酯或 N-（3-氟苯基）氨基甲酸酯重复单元的离散自褪色低聚氨基甲酸酯库。这些低聚氨基甲酸酯不仅会通过光介导的邻硝基氨基甲酸苄酯触发器的去除而发生级联 1,6- 消除解聚，而且在 MS/MS 条件下，即使没有紫外光照射，也会发生苄基-O 链接的选择性裂解。在水介质中，这些离散的低聚氨基甲酸乙酯会根据链长和骨架成分的不同自组装成不同的形态，如扁平纳米片、纳米纤维和纳米带。

  DOI：

  10.1002/anie.202306119

文献信息

• 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.
• [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.
• Controlled Self‐Assembly of Discrete Amphiphilic Oligourethanes with a Cascade Self‐Immolative Motif
  作者：Jie Xu、Changzhu Lv、Qiangqiang Shi、Jialin Zhang、Ning Wang、Guoying Zhang、Jinming Hu、Shiyong Liu

  DOI：10.1002/anie.202306119

  日期：2023.8.14

  Discrete polymers offer an excellent platform for comprehending the interplay between precise chain structures, distinctive self‐assembly behavior, and functional applications, whereas the development of discrete polymers with self‐immolative properties remains scarce. Here, we modularly synthesize a library of discrete self‐immolative oligourethanes containing N‐naphthylcarbamate or N‐(3‐fluorophenyl)carbamate repeating units via iterative stepwise growth. These oligourethanes undergo not only cascade 1,6‐elimination depolymerizations via photo‐mediated removal of o‐nitrobenzyl carbamate triggers but also selective cleavage of benzyl‐O linkages under MS/MS conditions even without UV light irradiation. In aqueous media, these discrete oligourethanes self‐assemble into different morphologies such as flat nanosheets, nanofibers, and nanoribbons, depending on the chain lengths and backbone compositions, and further morphological transitions are observed upon thermal annealing.

  摘要 离散聚合物为理解精确的链结构、独特的自组装行为和功能应用之间的相互作用提供了一个极好的平台，而具有自惰性的离散聚合物的开发仍然很少。在这里，我们通过迭代逐步生长的方法，模块化合成了含有 N-萘基氨基甲酸酯或 N-（3-氟苯基）氨基甲酸酯重复单元的离散自褪色低聚氨基甲酸酯库。这些低聚氨基甲酸酯不仅会通过光介导的邻硝基氨基甲酸苄酯触发器的去除而发生级联 1,6- 消除解聚，而且在 MS/MS 条件下，即使没有紫外光照射，也会发生苄基-O 链接的选择性裂解。在水介质中，这些离散的低聚氨基甲酸乙酯会根据链长和骨架成分的不同自组装成不同的形态，如扁平纳米片、纳米纤维和纳米带。