2-(4-bromophenyl)-N-(2,6-difluorophenyl)-2-oxoacetamide | 1373945-16-4

• 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: 2-(4-bromophenyl)-N-(2,6-difluorophenyl)-2-oxoacetamide
• CAS: 1373945-16-4
• 化学式: C₁₄H₈BrF₂NO₂
• 分子量: 340.124
• InChiKey: HCQYHDVUDLCGFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-(4-bromophenyl)-N-(2,6-difluorophenyl)-2-oxoacetamide 、 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 40.0h， 以67%的产率得到C₂₃H₁₆BrF₂N₃O
  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-(4-bromophenyl)-N-(2,6-difluorophenyl)-2-hydroxyacetamide 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到2-(4-bromophenyl)-N-(2,6-difluorophenyl)-2-oxoacetamide
  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

文献信息

• Triply Hydrogen-Bond-Directed Enantioselective Assembly of Pyrrolobenzo-1,4-diazine Skeletons with Quaternary Stereocenters
  作者：Xiaoming Shen、Yongtao Wang、Tiandi Wu、Zhenjun Mao、Xufeng Lin

  DOI：10.1002/chem.201500823

  日期：2015.6.15

  Highly efficient synthesis of optically enriched pyrrolobenzo‐1,4‐diazines bearing quaternary stereocenters has been realized through the chiral Brønsted acid‐catalyzed Pictet–Spengler reaction of 2‐(1H‐pyrrol‐1‐yl)anilines and α‐ketoamides in good to excellent yields and enantioselectivities. Computational studies suggest an unprecedented phenomenon whereby the chiral phosphoric acid catalyst employs

  通过手性布朗斯台德酸催化的2-（1 H-吡咯-1-基）苯胺和α-酮酰胺的Brønsted酸催化的Pictet-Spengler反应，已实现了具有四级立体中心的光学富集的吡咯并苯并-1,4-二嗪的高效合成。达到优异的收率和对映选择性。由此手性磷酸催化剂采用有吸引力的芳烃Ç计算研究表明了前所未有的现象 H⋅⋅⋅N氢键，以激活所述基板和通过三氢键相互作用诱导手性。