5-(4-fluorophenyl)-2-phenyl-3-(trifluoromethyl)furan | 143541-35-9

• 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-(4-fluorophenyl)-2-phenyl-3-(trifluoromethyl)furan
• CAS: 143541-35-9
• 化学式: C₁₇H₁₀F₄O
• 分子量: 306.259
• InChiKey: NAYUTUJOKKPUNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,4-difluoro-1-(4-fluorophenyl)-3-(trifluoromethyl)but-3-en-1-one 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-(4-fluorophenyl)-2-phenyl-3-(trifluoromethyl)furan
  参考文献：
  名称：

  Partially Fluorinated Heterocycles from 4,4-Bis(trifluoromethyl)-hetero-1,3-dienes via C–F Bond Activation – Synthesis of 2-Fluoro-3-(trifluoromethyl)furans

  摘要：

  An efficient synthesis of 2-fluoro-3-(trifluoromethyl)furans was developed. Keystep of the reaction sequence is a [4 + 1] cycloaddition reaction of tin(II)chloride to 4,4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes. At elevated temperatures the tin heterocycles are transformed into 1-aryl-4,4-difluoro-3-(trifluoromethyl)but-3-en-1-ones which on treatment with sodium hydride in dry DMF give 2-fluoro-3-(trifluoromethyl)furans. The single fluorine bound to C-(2) can be readily replaced by various N-, O-, S-, and C-nucleophiles and dinucleophiles.

  DOI：

  10.1007/s00706-007-0587-4

文献信息

• Transition-Metal-Free Synthesis of Trifluoromethylated Furans via a Bu3P-Mediated Tandem Acylation–Wittig Reaction
  作者：Wei Zhou、Maizhan Li

  DOI：10.1055/s-0040-1707263

  日期：2020.12

  A highly efficient nucleophilic addition–O-acylation–intramolecular Wittig reaction of β-trifluoromethyl α,β-enones is disclosed. This strategy features mild reaction conditions and provides a practical transition-metal-free method to a set of biologically significant trifluoromethylated furans in high yields with diverse functional groups.

  本文披露了一种高效的亲核加成-O-酰化-分子内Wittig反应，用于β-三氟甲基α,β-烯酮。该策略具有温和的反应条件，并提供了一种实用的无过渡金属方法，以高产率合成一系列具有生物学意义的三氟甲基呋喃，其中包含多种功能基团。

• Ein neues Verfahren zur positionsselektiven Einf�hrung von Trifluormethylgruppen in Heteroaromaten: Synthese von 3-Trifluormethylfuranen
  作者：Klaus Burger、Brigitte Helmreich

  DOI：10.1002/prac.19923340404

  日期：——

  Transformation of 4,4-bis(trifluoromethyl)-1-oxabuta-1,3-dienes (2) into 2-fluoro-3-trifluoromethylfurnas (4) can be achieved in a two step procedure by treatment with tin (II) chloride and sodium hydride. The fluorine atom at skeleton position 2 is replaced smoothly by various nucleophiles. The reaction sequence represents a preparatively simple method for the selective introduction of biologically relevant substituents into 3-trifluoromethylfurans.