dimethyl (2R,3S,4S)-3-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4-(2-methoxyphenyl)pyrrolidine-1,2-dicarboxylate | 946428-50-8

• 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: dimethyl (2R,3S,4S)-3-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4-(2-methoxyphenyl)pyrrolidine-1,2-dicarboxylate
• CAS: 946428-50-8
• 化学式: C₂₂H₂₉NO₉
• 分子量: 451.474
• InChiKey: FHELEZHIMJZYMM-UWWQBHOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,3S,4S)-3-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4-(2-methoxyphenyl)pyrrolidine-1,2-dicarboxylate 在 platinum(IV) oxide 盐酸 、 sodium hydroxide 、 氢气 、 双氧水 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 80.0 ℃ 、482.64 kPa 条件下， 反应 72.5h， 生成 1-benzyl-2-methyl 3α-methoxycarbonylmethyl-4α-(2-methoxyphenyl)pyrrolidine-1,2α-dicarboxylate
  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 palladium diacetate sodium hydride 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 dimethyl (2R,3S,4S)-3-(1,3-diethoxy-1,3-dioxopropan-2-yl)-4-(2-methoxyphenyl)pyrrolidine-1,2-dicarboxylate
  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.