N-[(1S,2R)-1-(4-Fluoro-phenyl)-4-iodo-2-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-butyl]-4-methyl-benzenesulfonamide | 866354-49-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(1S,2R)-1-(4-Fluoro-phenyl)-4-iodo-2-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-butyl]-4-methyl-benzenesulfonamide
• 英文别名: N-[(1S,2R)-1-(4-fluorophenyl)-4-iodo-2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidine-3-carbonyl]butyl]-4-methylbenzenesulfonamide
• CAS: 866354-49-6
• 化学式: C₂₇H₂₆FIN₂O₅S
• 分子量: 636.483
• InChiKey: IQQBYUDINHYUHM-UBFVSLLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(1S,2R)-1-(4-Fluoro-phenyl)-4-iodo-2-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-butyl]-4-methyl-benzenesulfonamide 在 lithium hydroxide 、 双氧水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 (2S,3R)-2-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  Asymmetric Halo-Mannich-Type Reaction Provides Access to Pyrrolidines and β-Proline Derivatives

  摘要：

  A new halo-Mannich-type reaction is reported using cyclopropyl carbonyl-derived enolates and sulfonyl-protected imines. Chiral oxazolidinones auxiliaries were found to be effective for completely controlling the stereochemistry of the products. Variations in the oxazolidinone, protecting group, and imine components show this to be a quite general reaction. The initial iodo-Mannich products were found to be readily cyclized in the presence of triethylamine to afford the resulting protected pyrrolidines, which could be readily deprotected under standard conditions.

  DOI：

  10.1021/jo0509051
• 作为产物：
  描述：

  N-(4-fluorobenzylidene)-4-methylbenzenesulfonamide 、 (4S)-3-(cyclopropanecarbonyl)-4-phenyl-1,3-oxazolidin-2-one 在 二乙基碘化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 9.5h， 生成 N-[(1S,2R)-1-(4-Fluoro-phenyl)-4-iodo-2-((S)-2-oxo-4-phenyl-oxazolidine-3-carbonyl)-butyl]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Asymmetric Halo-Mannich-Type Reaction Provides Access to Pyrrolidines and β-Proline Derivatives

  摘要：

  A new halo-Mannich-type reaction is reported using cyclopropyl carbonyl-derived enolates and sulfonyl-protected imines. Chiral oxazolidinones auxiliaries were found to be effective for completely controlling the stereochemistry of the products. Variations in the oxazolidinone, protecting group, and imine components show this to be a quite general reaction. The initial iodo-Mannich products were found to be readily cyclized in the presence of triethylamine to afford the resulting protected pyrrolidines, which could be readily deprotected under standard conditions.

  DOI：

  10.1021/jo0509051