3-Fluoroformylthiophene | 38144-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-Fluoroformylthiophene
• 英文别名: thiophene-3-carbonyl fluoride
• CAS: 38144-30-8
• 化学式: C₅H₃FOS
• 分子量: 130.143
• InChiKey: KWBUWSKVSLEWSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  164.4±13.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Fluoroformylthiophene 、 苄胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-benzylthiophene-3-carboxamide
  参考文献：
  名称：

  Palladium-Catalyzed Fluorocarbonylation Using N-Formylsaccharin as CO Source: General Access to Carboxylic Acid Derivatives

  摘要：

  N-Formylsaccharin, an easily accessible crystalline compound, has been employed as an efficient CO source in Pd-catalyzed fluorocarbonylation of aryl halides to afford the corresponding acyl fluorides in high yields. The reactions use a near-stoichiometric amount of the CO source (1.2 equiv) and tolerate diverse functional groups. The acyl fluorides obtained could be readily transformed into various carboxylic acid derivatives such as carboxylic acid, esters, thioesters, and amides in a one-pot procedure.

  DOI：

  10.1021/ol4026815
• 作为产物：
  描述：

  3-噻吩甲酸 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以71%的产率得到3-Fluoroformylthiophene
  参考文献：
  名称：

  Synthesis and characterization of thiophenes with fluorinated substituents

  摘要：

  The synthesis of several 3-(polyfluoro)thiophenes, which are possible precursors to conductive polythiophenes, is described. This report includes an improved synthesis of 3-trifluoromethylthiophene and the previously reported but uncharacterized 3-fluoroformylthiophene. The new compounds 1-(3-thienyl)-1H,2H,3H,3H-nonafluorohept-1-ene, l-(3-thienyl)-1H,2H,3H,3H-tridecafluoronon-1-ene, 1-(3-thenyl)-trifluoroacetate, 1-(3-thenyl)-heptafluorobutyrate, and 1-(3-thenyl)-3-fluorosulfuryltetrafluoroethylether are reported. The last compound is unstable and decomposes to 1-fluorosulfuryl-1-fluoroformyldifluoromethane and thenyl fluoride. More extensive data for the previously prepared 1-(3-thienyl)-1H,2H,2H,3H,3H-tridecafluoronon-1-ol and 1-(3-thienyl)-1H,2H,2H,3H,3H-nonafluoroheptan-1-ol are also included. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-1139(98)00289-9

文献信息

• Catalytic Acid Fluoride Synthesis via Carbonylation of Organic Bromides in the Presence Potassium Fluoride
  作者：Tamon Okano、Nobuyuki Harada、Jitsuo Kiji

  DOI：10.1246/bcsj.65.1741

  日期：1992.6

  Various aryl bromides were carbonylated under an atmospheric pressure of carbon monoxide in DMF in the presence of potassium fluoride to give aroyl fluorides in excellent yields. The carbonylation was promoted by the addition of phase transfer catalysts, but the contamination with water reduced the selectivity.

  在氟化钾的存在下，在一氧化碳的大气压下，在DMF中，各种芳基溴化物被羰基化，以优异的产率得到芳酰氟。通过添加相转移催化剂促进羰基化，但水的污染降低了选择性。
• Construction of C(CO)–C(CO) Bond via NHC-Catalyzed Radical Cross-Coupling Reaction
  作者：Hai-Bin Yang、Xiao-Fang Jin、Hui-Ying Jiang、Wenwei Luo

  DOI：10.1021/acs.orglett.3c00272

  日期：2023.3.24

  A C(sp2)–C(sp2) bond can be constructed via a photoredox/N-heterocyclic carbene (NHC)-cocatalyzed radical cross-coupling reaction, which provides a complementary strategy to classic electron pair processes. The present protocol represents the first example of an NHC-catalyzed two-component radical cross-coupling reaction involving C(sp2)-centered radical species. The decarboxylative acylation of oxamic

  AC(sp 2 )–C(sp 2 ) 键可以通过光氧化还原/N-杂环卡宾 (NHC) 共催化的自由基交叉偶联反应构建，这为经典电子对过程提供了互补策略。本协议代表了涉及以 C(sp 2 ) 为中心的自由基物种的 NHC 催化的双组分自由基交叉偶联反应的第一个示例。草氨酸与酰基氟的脱羧酰化反应在温和条件下进行，可以制备各种有用的 α-酮酰胺，包括空间拥挤的酰胺。
• Ritter Stephen K., Noftle Ronald E., Ward Amy E., J. E. Mitchell Sci. Soc, 109 (1993) N 4, S 262
  作者：Ritter Stephen K., Noftle Ronald E., Ward Amy E.

  DOI：——

  日期：——
• Palladium-Catalyzed Fluorocarbonylation Using <i>N</i>-Formylsaccharin as CO Source: General Access to Carboxylic Acid Derivatives
  作者：Tsuyoshi Ueda、Hideyuki Konishi、Kei Manabe

  DOI：10.1021/ol4026815

  日期：2013.10.18

  N-Formylsaccharin, an easily accessible crystalline compound, has been employed as an efficient CO source in Pd-catalyzed fluorocarbonylation of aryl halides to afford the corresponding acyl fluorides in high yields. The reactions use a near-stoichiometric amount of the CO source (1.2 equiv) and tolerate diverse functional groups. The acyl fluorides obtained could be readily transformed into various carboxylic acid derivatives such as carboxylic acid, esters, thioesters, and amides in a one-pot procedure.
• Synthesis and characterization of thiophenes with fluorinated substituents
  作者：S.K. Ritter、B.K. Hill、M.A. Odian、J. Dai、R.E. Noftle、G.L. Gard

  DOI：10.1016/s0022-1139(98)00289-9

  日期：1999.1

  The synthesis of several 3-(polyfluoro)thiophenes, which are possible precursors to conductive polythiophenes, is described. This report includes an improved synthesis of 3-trifluoromethylthiophene and the previously reported but uncharacterized 3-fluoroformylthiophene. The new compounds 1-(3-thienyl)-1H,2H,3H,3H-nonafluorohept-1-ene, l-(3-thienyl)-1H,2H,3H,3H-tridecafluoronon-1-ene, 1-(3-thenyl)-trifluoroacetate, 1-(3-thenyl)-heptafluorobutyrate, and 1-(3-thenyl)-3-fluorosulfuryltetrafluoroethylether are reported. The last compound is unstable and decomposes to 1-fluorosulfuryl-1-fluoroformyldifluoromethane and thenyl fluoride. More extensive data for the previously prepared 1-(3-thienyl)-1H,2H,2H,3H,3H-tridecafluoronon-1-ol and 1-(3-thienyl)-1H,2H,2H,3H,3H-nonafluoroheptan-1-ol are also included. (C) 1999 Elsevier Science S.A. All rights reserved.