N-(2,6-difluorophenyl)-2-oxooctanamide | 1373946-77-0

• 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: N-(2,6-difluorophenyl)-2-oxooctanamide
• CAS: 1373946-77-0
• 化学式: C₁₄H₁₇F₂NO₂
• 分子量: 269.291
• InChiKey: DDFDQNOMXLNMSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(2,6-difluorophenyl)-2-oxooctanamide 、 1H-吲哚-4-甲胺 在 (4S,5S)-2-Chloro-3,4-dimethyl-2,5-diphenyl-1-oxa-3-aza-2-silacyclopentane, 97% 作用下， 以 苯 为溶剂， 反应 26.0h， 以86%的产率得到(S)-N-(2,6-difluorophenyl)-3-hexyl-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline-3-carboxamide
  参考文献：
  名称：

  Direct and Highly Enantioselective Iso-Pictet–Spengler Reactions with α-Ketoamides: Access to Underexplored Indole Core Structures

  摘要：

  Direct, one-pot, operationally simple, and highly enantioselective iso-Pictet-Spengler reactions are reported. The reactions involve the condensation of either (1H-indol-4-yl)methanamine or 2-(1H-Indol-1-yl)ethanamine with a variety of alpha-ketoamides, followed by the addition of a simple and commercially available chiral silicon Lewis acid. These reactions are the first asymmetric examples of these cyclization modes and provide access to 3,3-disubstituted-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinolines and 1,1-disubstituted-1,2,3,4-tetrahydropyrazino[1,2-a]indoles, respectively, two relatively underexplored indole-based core structure motifs in medicinal chemistry.

  DOI：

  10.1021/ol300922b
• 作为产物：
  描述：

  2-氧代辛酸 在 吡啶 、 1,1-二氯甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 生成 N-(2,6-difluorophenyl)-2-oxooctanamide
  参考文献：
  名称：

  Direct and Highly Enantioselective Iso-Pictet–Spengler Reactions with α-Ketoamides: Access to Underexplored Indole Core Structures

  摘要：

  Direct, one-pot, operationally simple, and highly enantioselective iso-Pictet-Spengler reactions are reported. The reactions involve the condensation of either (1H-indol-4-yl)methanamine or 2-(1H-Indol-1-yl)ethanamine with a variety of alpha-ketoamides, followed by the addition of a simple and commercially available chiral silicon Lewis acid. These reactions are the first asymmetric examples of these cyclization modes and provide access to 3,3-disubstituted-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinolines and 1,1-disubstituted-1,2,3,4-tetrahydropyrazino[1,2-a]indoles, respectively, two relatively underexplored indole-based core structure motifs in medicinal chemistry.

  DOI：

  10.1021/ol300922b