6-(2-Methylcarbamoylmethyl-phenyl)-hex-5-ynoic acid methyl ester | 896101-39-6

• 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: 6-(2-Methylcarbamoylmethyl-phenyl)-hex-5-ynoic acid methyl ester
• CAS: 896101-39-6
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: IWCFANCZPOUHNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-(2-Methylcarbamoylmethyl-phenyl)-hex-5-ynoic acid methyl ester 在 bis(triphenylphosphine) palladium (Il) acetate 、 sodium ethanolate 、 potassium carbonate 、 碘甲烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以71%的产率得到methyl 4-(3-methyl-2-oxo-1H-3-benzazepin-4-yl)butanoate
  参考文献：
  名称：

  A regioselective synthesis of 3-benzazepinones via intramolecular hydroamidation of acetylenes

  摘要：

  Synthesis of 3-benzazepinones by palladium-catalyzed intramolecular addition of amides to alkynes is achieved. Phenyl acetylenes substituted in the ortho-position with tethered amide functionality were prepared in a few steps from readily available starting materials. It was found that 5% Pd(OAc)(2)(PPh3)(2) and KOH most effectively promoted cyclization. When the tethered group is an acetamide and an alkyl substituent is on the acetylene unit, regioselective 3-benzazepinone synthesis could be achieved in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.198
• 作为产物：
  描述：

  2-碘苯乙酸 在 copper(l) iodide 、 氯化亚砜 、 bis(triphenylphosphine) palladium (Il) acetate 、 三乙胺 作用下， 反应 3.0h， 生成 6-(2-Methylcarbamoylmethyl-phenyl)-hex-5-ynoic acid methyl ester
  参考文献：
  名称：

  A regioselective synthesis of 3-benzazepinones via intramolecular hydroamidation of acetylenes

  摘要：

  Synthesis of 3-benzazepinones by palladium-catalyzed intramolecular addition of amides to alkynes is achieved. Phenyl acetylenes substituted in the ortho-position with tethered amide functionality were prepared in a few steps from readily available starting materials. It was found that 5% Pd(OAc)(2)(PPh3)(2) and KOH most effectively promoted cyclization. When the tethered group is an acetamide and an alkyl substituent is on the acetylene unit, regioselective 3-benzazepinone synthesis could be achieved in good yields. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.198