(2R,3S,4S)-3-(carboxymethyl)-1-(methoxycarbonyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylic acid | 946428-56-4

• 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,3S,4S)-3-(carboxymethyl)-1-(methoxycarbonyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylic acid
• CAS: 946428-56-4
• 化学式: C₁₆H₁₉NO₇
• 分子量: 337.329
• InChiKey: ODYQFDPXCYGEJO-MISXGVKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113.37
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-3-(carboxymethyl)-1-(methoxycarbonyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylic acid 在 盐酸 作用下， 反应 40.0h， 以75%的产率得到(2R,3S,4S)-3-(carboxymethyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Regio- and Stereoselective Heck Arylations of N-Carbomethoxy-l- 3-Dehydroproline Methyl Ester with Arenediazonium Salts. Total Synthesis of Neuroexcitatory Aryl Kainoids

  摘要：

  The Heck arylation of N-carbomethoxy-(L)-3-dehydroproline methyl ester with arenediazonium tetrafluoroborates produced chiral 4-aryldehydroproline derivatives in moderate to good yields in a highly regio- and stereocontrolled fashion. A rationale for the unexpected high regioselectivity is provided using Deeth's model. Heck adduct 15 (G = o-CH3O) was converted into several aryl kainoids using concise and efficient routes.

  DOI：

  10.1021/ol070980t
• 作为产物：
  描述：

  2-methoxyphenyldiazonium tetrafluoroborate 在 platinum(IV) oxide 、 palladium diacetate 盐酸 、 氢气 、 双氧水 、 sodium hydride 、 溶剂黄146 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 80.0 ℃ 、482.64 kPa 条件下， 反应 34.5h， 生成 (2R,3S,4S)-3-(carboxymethyl)-1-(methoxycarbonyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Regio- and Stereoselective Heck Arylations of N-Carbomethoxy-l- 3-Dehydroproline Methyl Ester with Arenediazonium Salts. Total Synthesis of Neuroexcitatory Aryl Kainoids

  摘要：

  The Heck arylation of N-carbomethoxy-(L)-3-dehydroproline methyl ester with arenediazonium tetrafluoroborates produced chiral 4-aryldehydroproline derivatives in moderate to good yields in a highly regio- and stereocontrolled fashion. A rationale for the unexpected high regioselectivity is provided using Deeth's model. Heck adduct 15 (G = o-CH3O) was converted into several aryl kainoids using concise and efficient routes.

  DOI：

  10.1021/ol070980t