(Z)-2-fluoro-N-methoxy-N-methyl-3-(2-thienyl)propenamide | 1149578-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (Z)-2-fluoro-N-methoxy-N-methyl-3-(2-thienyl)propenamide
• 英文别名: (Z)-2-fluoro-N-methoxy-N-methyl-3-thiophen-2-ylprop-2-enamide
• CAS: 1149578-09-5
• 化学式: C₉H₁₀FNO₂S
• 分子量: 215.248
• InChiKey: QCDXQGMGXCRNNA-VURMDHGXSA-N

物化性质

• 沸点：
  277.7±50.0 °C(predicted)
• 密度：
  1.274±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 2-(benzo[d]thiazol-2-ylsulfonyl)-2-fluoro-N-methoxy-N-methylacetamide 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以99%的产率得到(Z)-2-fluoro-N-methoxy-N-methyl-3-(2-thienyl)propenamide
  参考文献：
  名称：

  α-Fluorovinyl Weinreb Amides and α-Fluoroenones from a Common Fluorinated Building Block

  摘要：

  Synthesis and reactivity of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfonyl)fluoroacetamide, a building block for Julia olefination, is reported. This reagent undergoes condensation reactions with aldehydes and cyclic ketones to give alpha-fluorovinyl Weinreb amides. Olefination reactions proceed under mild, DBU-mediated conditions, or in the presence of NaH. DBU-mediated condensations proceed with either E- or Z-selectivity, depending upon reaction conditions, whereas NaH-mediated reactions are >= 98% Z-stereoselective. Conversion of the Weinreb amide moiety in N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide to ketones, followed by oxidation, resulted in another set of olefination reagents, namely (1,3-benzothiazol-2-ylsulfonyl)fluoromethyl phenyl and propyl ketones. In the presence of DBU, these compounds react with aldehydes tested to give alpha-fluoroenones with high Z-selectivity. The use of N-methoxy-N-methyl-(1,3-benzothiazol-2-ylsulfanyl)fluoroacetamide as a common fluorinated intermediate in the synthesis of alpha-fluorovinyl Weinreb amides and alpha-fluoroenones has been demonstrated. Application of the Weinreb amide to alpha-flu-fluoro allyl amine synthesis is also shown.

  DOI：

  10.1021/jo802784w