2-fluoro-5-(thien-2-yl)-3-(trifluoromethyl)furan | 140860-90-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 2-fluoro-5-(thien-2-yl)-3-(trifluoromethyl)furan
• 英文别名: 2-Fluoro-5-(thiophen-2-yl)-3-(trifluoromethyl)furan；2-fluoro-5-thiophen-2-yl-3-(trifluoromethyl)furan
• CAS: 140860-90-8
• 化学式: C₉H₄F₄OS
• 分子量: 236.19
• InChiKey: DJPNKHNQBGEFQM-UHFFFAOYSA-N

物化性质

• 沸点：
  35 °C(Press: 0.1 Torr)
• 密度：
  1.433±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(4-氯苯基)-2-[(2-羟基乙基)甲基氨基]-3-(三氟甲基)呋喃 、 2-fluoro-5-(thien-2-yl)-3-(trifluoromethyl)furan 以 1,4-二氧六环 为溶剂， 以38%的产率得到2-[methyl[5-(4-chlorophenyl)-3-(trifluoromethyl)fur-2-yl]amino]-1-[5-(thien-2-yl)-3-(trifluoromethyl)fur-2-yloxy]ethane
  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
• 作为产物：
  描述：

  4,4-difluoro-1-(thien-2-yl)-3-(trifluoromethyl)but-3-en-1-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以63%的产率得到2-fluoro-5-(thien-2-yl)-3-(trifluoromethyl)furan
  参考文献：
  名称：

  Synthesis of 3-trifluoromethylfurans from β,β-bis(trifluoromethyl)α,β-unsaturated ketones and tin(II) chloride

  摘要：

  报道了一种新的合成3-三氟甲基取代呋喃9和10的模块化策略，通过β,β-双(三氟甲基)α,β-不饱和酮2经过还原氟消除和消去1,5-电环化反应实现。

  DOI：

  10.1039/c39920000348

文献信息

• Synthesis of 3-trifluoromethylfurans from β,β-bis(trifluoromethyl)α,β-unsaturated ketones and tin(<scp>II</scp>) chloride
  作者：Klaus Burger、Brigitte Helmreich

  DOI：10.1039/c39920000348

  日期：——

  A new building block strategy for the synthesis of 3-trifluoromethyl-substituted furans 9 and 10 is described from β,β-bis(trifluoromethyl)α,β-unsaturated ketones 2via reductive fluoride elimination and 1,5-electrocyclization with elimination.

  报道了一种新的合成3-三氟甲基取代呋喃9和10的模块化策略，通过β,β-双(三氟甲基)α,β-不饱和酮2经过还原氟消除和消去1,5-电环化反应实现。
• 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.
• Partially Fluorinated Heterocycles from 4,4-Bis(trifluoromethyl)-hetero-1,3-dienes via C–F Bond Activation – Synthesis of 2-Fluoro-3-(trifluoromethyl)furans
  作者：Klaus Burger、Brigitte Helmreich、Lothar Hennig、Jan Spengler、Fernando Albericio、Annett Fuchs

  DOI：10.1007/s00706-007-0587-4

  日期：2007.3

  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.