N-((1S)-2-hydroxy-1-methylethyl)-2-aminobenzamide | 209850-71-5

• 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-((1S)-2-hydroxy-1-methylethyl)-2-aminobenzamide
• 英文别名: 2-amino-N-[(2S)-1-hydroxypropan-2-yl]benzamide
• CAS: 209850-71-5
• 化学式: C₁₀H₁₄N₂O₂
• 分子量: 194.233
• InChiKey: BPTVGPHRTVRXCI-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-((1S)-2-hydroxy-1-methylethyl)-2-aminobenzamide 在 sodium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 2-[(4S)-4-methyl-4,5-dihydro-1,3-oxazol-2-yl]aniline
  参考文献：
  名称：

  Synthesis of Chiral Bis(dihydrooxazolylphenyl)oxalamides, a New Class of Tetradentate Ligands for Asymmetric Catalysis

  摘要：

  Enantiomerically pure N,N'-bis[2-(4,5-dihydrooxazol-2-yl)phenyl]oxalamides are readily prepared from 2-(2-aminophenyl)-4,5-dihydrooxazoles and oxalyl chloride. The structures of the corresponding nickel and copper complexes were determined by X-ray analysis. Ruthenium complexes, prepared in situ from RuCl3 and the corresponding ligands, catalyze the enantioselective epoxidation of trans-stilbene to afford trans-1,2-diphenyloxirane with up to 69% ee. The cobalt complexes were tested as catalysts in Michael reactions of malonates with chalcone (up to 89% ee).

  DOI：

  10.1002/(sici)1521-3765(19980515)4:5<818::aid-chem818>3.0.co;2-#
• 作为产物：
  描述：

  靛红酸酐 、 L-氨基丙醇 以 1,4-二氧六环 为溶剂， 以60%的产率得到N-((1S)-2-hydroxy-1-methylethyl)-2-aminobenzamide
  参考文献：
  名称：

  Synthesis of Chiral Bis(dihydrooxazolylphenyl)oxalamides, a New Class of Tetradentate Ligands for Asymmetric Catalysis

  摘要：

  Enantiomerically pure N,N'-bis[2-(4,5-dihydrooxazol-2-yl)phenyl]oxalamides are readily prepared from 2-(2-aminophenyl)-4,5-dihydrooxazoles and oxalyl chloride. The structures of the corresponding nickel and copper complexes were determined by X-ray analysis. Ruthenium complexes, prepared in situ from RuCl3 and the corresponding ligands, catalyze the enantioselective epoxidation of trans-stilbene to afford trans-1,2-diphenyloxirane with up to 69% ee. The cobalt complexes were tested as catalysts in Michael reactions of malonates with chalcone (up to 89% ee).

  DOI：

  10.1002/(sici)1521-3765(19980515)4:5<818::aid-chem818>3.0.co;2-#

文献信息

• Synthesis of Chiral Bis(dihydrooxazolylphenyl)oxalamides, a New Class of Tetradentate Ligands for Asymmetric Catalysis
  作者：Nicole End、Ludwig Macko、Margareta Zehnder、Andreas Pfaltz

  DOI：10.1002/(sici)1521-3765(19980515)4:5<818::aid-chem818>3.0.co;2-#

  日期：1998.5.15

  Enantiomerically pure N,N'-bis[2-(4,5-dihydrooxazol-2-yl)phenyl]oxalamides are readily prepared from 2-(2-aminophenyl)-4,5-dihydrooxazoles and oxalyl chloride. The structures of the corresponding nickel and copper complexes were determined by X-ray analysis. Ruthenium complexes, prepared in situ from RuCl3 and the corresponding ligands, catalyze the enantioselective epoxidation of trans-stilbene to afford trans-1,2-diphenyloxirane with up to 69% ee. The cobalt complexes were tested as catalysts in Michael reactions of malonates with chalcone (up to 89% ee).