(S)-3-[(2S,3R)-2-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-3-carbonyl]-4-phenyl-oxazolidin-2-one | 866354-58-7

• 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: (S)-3-[(2S,3R)-2-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-3-carbonyl]-4-phenyl-oxazolidin-2-one
• 英文别名: (4S)-3-[(2S,3R)-2-(4-fluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine-3-carbonyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 866354-58-7
• 化学式: C₂₇H₂₅FN₂O₅S
• 分子量: 508.57
• InChiKey: NSIZKANPMLEHAU-UBFVSLLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-3-[(2S,3R)-2-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-3-carbonyl]-4-phenyl-oxazolidin-2-one 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 以96%的产率得到(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 在 二乙基碘化铝 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 11.5h， 生成 (S)-3-[(2S,3R)-2-(4-Fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-3-carbonyl]-4-phenyl-oxazolidin-2-one
  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

文献信息

• Asymmetric Halo-Mannich-Type Reaction Provides Access to Pyrrolidines and β-Proline Derivatives
  作者：Cody Timmons、Li Guo、Junying Liu、John F. Cannon、Guigen Li

  DOI：10.1021/jo0509051

  日期：2005.9.1

  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.