(2R,3R,4S)-3-(carboxymethyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylic acid

• 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,3R,4S)-3-(carboxymethyl)-4-(2-methoxyphenyl)pyrrolidine-2-carboxylic acid
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: RPYRLXFYICBMOZ-GIPNMCIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-methoxyphenyldiazonium tetrafluoroborate 在 palladium diacetate 盐酸 、 sodium hydride 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 84.0h， 生成 (2R,3R,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

文献信息

• Regio- and Stereoselective Heck Arylations of <i>N</i>-Carbomethoxy-<scp>l</scp>- 3-Dehydroproline Methyl Ester with Arenediazonium Salts. Total Synthesis of Neuroexcitatory Aryl Kainoids
  作者：Kezia Peixoto da Silva、Marla Narciso Godoi、Carlos Roque Duarte Correia

  DOI：10.1021/ol070980t

  日期：2007.7.1

  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.