5-vinyl-2-furanic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-vinyl-2-furanic acid
• 英文别名: 5-Ethenylfuran-2-carboxylic acid
• 化学式: C₇H₆O₃
• 分子量: 138.123
• InChiKey: OLHXUVYOYZUYPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-vinyl-2-furanic acid 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 25.0 ℃ 、103.42 kPa 条件下， 以45 %的产率得到5-乙基呋喃-2-羧酸
  参考文献：
  名称：

  [EN] BICYCLIC PHTHALAZIN-1(2H)-ONE DERIVATIVES AND RELATED USES
  [FR] DÉRIVÉS BICYCLIQUES DE PHTALAZIN-1(2H)-ONE ET UTILISATIONS ASSOCIÉES

  摘要：

  The present disclosure relates to compounds of Formula (III): and to their pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inflammatory, autoinflammatory and autoimmune diseases and cancers.

  公开号：

  WO2023133271A1
• 作为产物：
  描述：

  5-溴-2-糠酸 、 乙烯基三乙氧基硅烷 在 sodium hydroxide 、 palladium diacetate 作用下， 以 水 为溶剂， 反应 3.08h， 以87%的产率得到5-vinyl-2-furanic acid
  参考文献：
  名称：

  Mechanistic Studies on the Pd-Catalyzed Vinylation of Aryl Halides with Vinylalkoxysilanes in Water: The Effect of the Solvent and NaOH Promoter

  摘要：

  The mechanism of the Pd-catalyzed vinylation of aryl halides with vinylalkoxysilanes in water has been studied using different catalytic precursors. The NaOH promoter converts the initial vinylalkoxysilane into a highly reactive water-soluble vinylsilanolate species. Similarly, deuterium-labeling experiments have shown that, irrespective of the catalytic precursor used, vinylation occurs exclusively at the CH vinylic functionality via a Heck reaction and not at the C-Si bond via a Hiyama cross-coupling. The involvement of a Heck mechanism is interpreted in terms of the reduced nucleophilicity of the base in water, which disfavors the transmetalation step. The Heck product (beta-silylvinylarene) undergoes partial desilylation, with formation of a vinylarene, by three different routes: (a) hydrolytic desilylation by the aqueous solvent (only at high temperature); (b) transmetalation of the silyl olefin on the PdH Heck intermediate followed by reductive elimination of vinylarene; (c) reinsertion of the silyl olefin into the PdH bond of the Heck intermediate followed by beta-Si syn-elimination. Both the Hiyama and Heck catalytic cycles and desilylation mechanisms b and c have been computationally evaluated for the [Pd(en)Cl-2] precursor in water as solvent. The calculated Gibbs energy barriers support the reinsertion route proposed on the basis of the experimental results.

  DOI：

  10.1021/ja404255u

文献信息

• The Stille cross coupling reactions on solid support. Link to solution phase directed ortho metalation. An ester linker approach to styryl, biaryl and heterobiaryl car☐ylic acids
  作者：Sylvie Chamoin、Stephen Houldsworth、Victor Snieckus

  DOI：10.1016/s0040-4039(98)00778-3

  日期：1998.6

  The synthesis of the titled compounds by Stille cross coupling on Merrifield resin — linked halo benzoates with stannanes followed by LiOH hydrolysis is reported.

  据报道，通过在Merrifield树脂上进行的Stille交叉偶联反应合成了标题的化合物，即用锡烷连接卤代苯甲酸酯，然后进行LiOH水解。
• Mechanistic Studies on the Pd-Catalyzed Vinylation of Aryl Halides with Vinylalkoxysilanes in Water: The Effect of the Solvent and NaOH Promoter
  作者：Alvaro Gordillo、Manuel A. Ortuño、Carmen López-Mardomingo、Agustí Lledós、Gregori Ujaque、Ernesto de Jesús

  DOI：10.1021/ja404255u

  日期：2013.9.18

  The mechanism of the Pd-catalyzed vinylation of aryl halides with vinylalkoxysilanes in water has been studied using different catalytic precursors. The NaOH promoter converts the initial vinylalkoxysilane into a highly reactive water-soluble vinylsilanolate species. Similarly, deuterium-labeling experiments have shown that, irrespective of the catalytic precursor used, vinylation occurs exclusively at the CH vinylic functionality via a Heck reaction and not at the C-Si bond via a Hiyama cross-coupling. The involvement of a Heck mechanism is interpreted in terms of the reduced nucleophilicity of the base in water, which disfavors the transmetalation step. The Heck product (beta-silylvinylarene) undergoes partial desilylation, with formation of a vinylarene, by three different routes: (a) hydrolytic desilylation by the aqueous solvent (only at high temperature); (b) transmetalation of the silyl olefin on the PdH Heck intermediate followed by reductive elimination of vinylarene; (c) reinsertion of the silyl olefin into the PdH bond of the Heck intermediate followed by beta-Si syn-elimination. Both the Hiyama and Heck catalytic cycles and desilylation mechanisms b and c have been computationally evaluated for the [Pd(en)Cl-2] precursor in water as solvent. The calculated Gibbs energy barriers support the reinsertion route proposed on the basis of the experimental results.
• [EN] BICYCLIC PHTHALAZIN-1(2H)-ONE DERIVATIVES AND RELATED USES<br/>[FR] DÉRIVÉS BICYCLIQUES DE PHTALAZIN-1(2H)-ONE ET UTILISATIONS ASSOCIÉES
  申请人：[en]NODTHERA LIMITED

  公开号：WO2023133271A1

  公开（公告）日：2023-07-13

  The present disclosure relates to compounds of Formula (III): and to their pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as inflammatory, autoinflammatory and autoimmune diseases and cancers.