(2R,4R,1'S)-1-(1'-phenylethyl)-4-hydroxy-proline methyl ester | 176966-56-6

• 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: (2R,4R,1'S)-1-(1'-phenylethyl)-4-hydroxy-proline methyl ester
• 英文别名: methyl (2R,4R)-4-hydroxy-1-[(1S)-1-phenylethyl]pyrrolidine-2-carboxylate
• CAS: 176966-56-6
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: JJILFWLIIMEPDD-CYZMBNFOSA-N

物化性质

• 沸点：
  353.0±42.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R,1'S)-1-(1'-phenylethyl)-4-hydroxy-proline methyl ester 在 palladium dihydroxide 氢气 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 顺式-4-羟基-D-脯氨酸甲酯
  参考文献：
  名称：

  Stereoselective synthesis of unnatural aminoacids cis-4-hydroxyproline and bulgecinine

  摘要：

  A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively, The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2), (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00079-1
• 作为产物：
  描述：

  甲醇 、 在 sodium carbonate 作用下， 反应 24.0h， 以90%的产率得到(2R,4R,1'S)-1-(1'-phenylethyl)-4-hydroxy-proline methyl ester
  参考文献：
  名称：

  Stereoselective synthesis of unnatural aminoacids cis-4-hydroxyproline and bulgecinine

  摘要：

  A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively, The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2), (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00079-1

文献信息

• Stereoselective synthesis of unnatural aminoacids cis-4-hydroxyproline and bulgecinine
  作者：Alessandra Madau、Gianni Porzi、Sergio Sandri

  DOI：10.1016/0957-4166(96)00079-1

  日期：1996.3

  A new stereoselective synthesis of both (2R,4R)- and (2S,4S)-4-hydroxy-proline and (+)- and (-)-bulgecinine was performed starting from synthons 1 or 1', respectively, The synthetic route has been established via a novel assisted cleavage of a disubstituted amide in mild conditions and successive stereocontrolled iodocyclization (Schemes 1 and 2), (C) 1996 Elsevier Science Ltd