(E)-2-fluoro-N-methoxy-N-methyl-3-(2-naphthyl)propenamide | 1149578-35-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-fluoro-N-methoxy-N-methyl-3-(2-naphthyl)propenamide
• 英文别名: (E)-2-fluoro-N-methoxy-N-methyl-3-naphthalen-2-ylprop-2-enamide
• CAS: 1149578-35-7
• 化学式: C₁₅H₁₄FNO₂
• 分子量: 259.28
• InChiKey: CSNVNWNDBMNBPO-GXDHUFHOSA-N

物化性质

• 沸点：
  372.3±52.0 °C(predicted)
• 密度：
  1.214±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(benzo[d]thiazol-2-ylsulfonyl)-2-fluoro-N-methoxy-N-methylacetamide 、 2-萘甲醛 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (Z)-2-fluoro-N-methoxy-N-methyl-3-(2-naphthyl)propenamide 、 (E)-2-fluoro-N-methoxy-N-methyl-3-(2-naphthyl)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

文献信息

• α-Fluorovinyl Weinreb Amides and α-Fluoroenones from a Common Fluorinated Building Block
  作者：Arun K. Ghosh、Shaibal Banerjee、Saikat Sinha、Soon Bang Kang、Barbara Zajc

  DOI：10.1021/jo802784w

  日期：2009.5.15

  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.