5-(4-氯苯基)-2-[(2-羟基乙基)甲基氨基]-3-(三氟甲基)呋喃 | 1008531-70-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 5-(4-氯苯基)-2-[(2-羟基乙基)甲基氨基]-3-(三氟甲基)呋喃
• 英文名称: 5-(4-chlorophenyl)-2-[(2-hydroxyethyl)methylamino]-3-(trifluoromethyl)furan
• 英文别名: 2-[[5-(4-chlorophenyl)-3-(trifluoromethyl)furan-2-yl]-methylamino]ethanol
• CAS: 1008531-70-1
• 化学式: C₁₄H₁₃ClF₃NO₂
• 分子量: 319.711
• InChiKey: GBKMDFRXMWXMOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.6
• 氢给体数：
  1
• 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：

  1-(4-Chloro-phenyl)-4,4,4-trifluoro-3-trifluoromethyl-but-2-en-1-one 在 sodium hydride 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 2.0h， 生成 5-(4-氯苯基)-2-[(2-羟基乙基)甲基氨基]-3-(三氟甲基)呋喃
  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

• 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.