2-amino-N-(2-methyl-propenyl)-benzamide

• 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-amino-N-(2-methyl-propenyl)-benzamide
• 英文别名: 2-amino-N-(2-methylprop-1-enyl)benzamide
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: NXBARBXGYLCAMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-N-(2-methyl-propenyl)-benzamide 在 ((R,R)-4,4’-bis(2-phenylnaphthyl-1-yl)-2,2’-binaphthyl-3,3’-diyl)hydrogen phosphate 、 sodium carbonate 、 Selectfluor 作用下， 以 甲苯 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Enantioselective Synthesis of Fluoro–Dihydroquinazolones and −Benzooxazinones by Fluorination-Initiated Asymmetric Cyclization Reactions

  摘要：

  Stereoselective synthesis of two fluorine-bearing drug-like scaffolds, dihydroquinazolone and benzooxazinone, has been accomplished through asymmetric fluorocyclization reactions initiated by the fluorination process. The reaction employs double axially chiral anionic phase-transfer catalysts to achieve high diastereo- and enantioselectivities, and a wide range of fluorine-containing dihydroquinazolones were obtained (>20:1 dr, up to 98% ee).

  DOI：

  10.1021/acscatal.5b02182
• 作为产物：
  描述：

  1-溴-2-甲基-1-丙烯 、 2-氨基苯甲酰胺 在 copper(l) iodide 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以81%的产率得到2-amino-N-(2-methyl-propenyl)-benzamide
  参考文献：
  名称：

  Copper-Catalyzed Coupling of Amides and Carbamates with Vinyl Halides

  摘要：

  A general and efficient copper-catalyzed method for the amidation of vinyl bromides and iodides has been developed. This protocol uses a combination of 5 mol % copper iodide and 20 mol % N,N'-dimethyl ethylenediamine. Substrates bearing ester, silyl ether, and amino groups were successfully coupled under the reaction conditions. The double bond geometry of the vinyl halides was retained under the reaction conditions.

  DOI：

  10.1021/ol035355c

文献信息

• Copper-Catalyzed Coupling of Amides and Carbamates with Vinyl Halides
  作者：Lei Jiang、Gabriel E. Job、Artis Klapars、Stephen L. Buchwald

  DOI：10.1021/ol035355c

  日期：2003.10.1

  A general and efficient copper-catalyzed method for the amidation of vinyl bromides and iodides has been developed. This protocol uses a combination of 5 mol % copper iodide and 20 mol % N,N'-dimethyl ethylenediamine. Substrates bearing ester, silyl ether, and amino groups were successfully coupled under the reaction conditions. The double bond geometry of the vinyl halides was retained under the reaction conditions.
• Enantioselective Synthesis of Fluoro–Dihydroquinazolones and −Benzooxazinones by Fluorination-Initiated Asymmetric Cyclization Reactions
  作者：Kenichi Hiramatsu、Takashi Honjo、Vivek Rauniyar、F. Dean Toste

  DOI：10.1021/acscatal.5b02182

  日期：2016.1.4

  Stereoselective synthesis of two fluorine-bearing drug-like scaffolds, dihydroquinazolone and benzooxazinone, has been accomplished through asymmetric fluorocyclization reactions initiated by the fluorination process. The reaction employs double axially chiral anionic phase-transfer catalysts to achieve high diastereo- and enantioselectivities, and a wide range of fluorine-containing dihydroquinazolones were obtained (>20:1 dr, up to 98% ee).