(4S)-2-benzyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester

• 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: (4S)-2-benzyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester
• 英文别名: methyl (4S)-2-benzyl-4,5-dihydro-1,3-thiazole-4-carboxylate
• 化学式: C₁₂H₁₃NO₂S
• 分子量: 235.307
• InChiKey: QZYVYPFMHLQSPP-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙腈 、 alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (4S)-2-benzyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  An Enantioselective Ketene−Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones

  摘要：

  Previously, a method for the stereoselective synthesis of P-lactams, starting from 2H-Delta (2)-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-Delta (2)-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 --> 78 degreesC. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 --> 64 degreesC led to the desired 2-pyridinones;in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different Delta (2)-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.

  DOI：

  10.1021/jo015794u

文献信息

• An Enantioselective Ketene−Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones
  作者：Hans Emtenäs、Lisa Alderin、Fredrik Almqvist

  DOI：10.1021/jo015794u

  日期：2001.10.1

  Previously, a method for the stereoselective synthesis of P-lactams, starting from 2H-Delta (2)-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-Delta (2)-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 --> 78 degreesC. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 --> 64 degreesC led to the desired 2-pyridinones;in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different Delta (2)-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.