(2S,3R)-3-(4-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid | 402580-39-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,3R)-3-(4-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid
• CAS: 402580-39-6
• 化学式: C₁₆H₂₀ClNO₆
• 分子量: 357.791
• InChiKey: NMWZEYAAGIAPFN-YPMHNXCESA-N

物化性质

• 沸点：
  527.1±50.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112.93
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(4-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid 在 三氟乙酸 作用下， 生成 (2S,3R)-3-(4-chlorophenyl)-glutamic acid
  参考文献：
  名称：

  Synthesis of homochiral 3-substituted glutamic acids and prolines from pyroglutamic acid

  摘要：

  Efficient syntheses of (2S,3S)-methylproline (5a) and (2S,3R)-phenylproline (5b) are described, starting from the readily available pyroglutaminol derivatives 2a and 2b via conjugate 1-4-addition of organocuprates to 1. Catalytic hydrogenation of 3 from the least hindered alpha-side furnishes 6, which is transformed to (2S,3R)-methylproline (7). 3-Substituted glutamic acids 8c,d are provided by a four step procedure from 2c,d.

  DOI：

  10.1016/s0957-4166(00)86204-7
• 作为产物：
  描述：

  2S,3R-1-t-butoxycarbonyl-3-(4-chlorophenyl)-5-oxo-pyrrolidine-2-carboxylic acid 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-3-(4-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid
  参考文献：
  名称：

  Synthesis of homochiral 3-substituted glutamic acids and prolines from pyroglutamic acid

  摘要：

  Efficient syntheses of (2S,3S)-methylproline (5a) and (2S,3R)-phenylproline (5b) are described, starting from the readily available pyroglutaminol derivatives 2a and 2b via conjugate 1-4-addition of organocuprates to 1. Catalytic hydrogenation of 3 from the least hindered alpha-side furnishes 6, which is transformed to (2S,3R)-methylproline (7). 3-Substituted glutamic acids 8c,d are provided by a four step procedure from 2c,d.

  DOI：

  10.1016/s0957-4166(00)86204-7