4-fluoro-N-methoxy-N-methyl-2-(phenylethynyl)benzamide | 1262282-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-fluoro-N-methoxy-N-methyl-2-(phenylethynyl)benzamide
• 英文别名: 4-fluoro-N-methoxy-N-methyl-2-(2-phenylethynyl)benzamide
• CAS: 1262282-48-3
• 化学式: C₁₇H₁₄FNO₂
• 分子量: 283.302
• InChiKey: QKYWBTCSMLWAJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-fluoro-N-methoxy-N-methyl-2-(phenylethynyl)benzamide 在 N-氯代丁二酰亚胺 、 copper dichloride 作用下， 以 乙腈 为溶剂， 以88%的产率得到(E)-3-[chloro(phenyl)methylene]-5-fluoroisobenzofuran-1(3H)-one
  参考文献：
  名称：

  Copper(II)Chloride-Mediated Cyclization Reaction ofN-Alkoxy-ortho-alkynylbenzamides

  摘要：

  A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.

  DOI：

  10.1021/ol1029035
• 作为产物：
  描述：

  4-氟-2-碘苯甲酸 在 copper(l) iodide 、 四(三苯基膦)钯 、 草酰氯 、 正丁胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 4-fluoro-N-methoxy-N-methyl-2-(phenylethynyl)benzamide
  参考文献：
  名称：

  Copper(II)Chloride-Mediated Cyclization Reaction ofN-Alkoxy-ortho-alkynylbenzamides

  摘要：

  A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.

  DOI：

  10.1021/ol1029035

文献信息

• Palladium-Catalyzed Synthesis of Isoquinolinones via Sequential Cyclization and N-O Bond Cleavage of N-Methoxy-o-alkynylbenzamides
  作者：Masafumi Ueda、Okiko Miyata、Manita Jithunsa、Naoki Aoi、Shoichi Sugita、Tetsuya Miyoshi

  DOI：10.1055/s-0032-1318159

  日期：——

  A palladium-catalyzed controlled 6-endo-dig cyclization process has been developed for the chemoselective synthesis of isoquinolin-1-ones from N-alkoxy-o-alkynylbenzamides. The mechanism and scope of the reaction have also been investigated. Deuterium-labeling studies were used to confirm the intramolecular 1,5-hydrogen shift as a key step in the transformation.
• Copper(II)Chloride-Mediated Cyclization Reaction of<i>N</i>-Alkoxy-<i>ortho</i>-alkynylbenzamides
  作者：Manita Jithunsa、Masafumi Ueda、Okiko Miyata

  DOI：10.1021/ol1029035

  日期：2011.2.4

  A regioselective intramolecular cyclization/halogenation reaction of N-alkoxy-o-alkynylbenzamides with CuCl2/NCS was developed. The corresponding 3-(chloromethylene)isobenzofuran-1-ones were exclusively obtained via 5-exo-dig cyclization in moderate to excellent yields within 0.5-1 h. This approach has been successfully used to synthesize a biaryl compound by the Suzuki-Miyaura reaction.