methyl (2S)-2-(hydroxymethyl)-2,3-dihydropyrrole-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: methyl (2S)-2-(hydroxymethyl)-2,3-dihydropyrrole-1-carboxylate
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: IAPZFALZKLLBCN-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methoxybenzenediazonium tetrafluoroborate 、 methyl (2S)-2-(hydroxymethyl)-2,3-dihydropyrrole-1-carboxylate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium acetate 作用下， 以 乙腈 为溶剂， 以92%的产率得到methyl (2S)-2-(hydroxymethyl)-5-(4-methoxyphenyl)-2,5-dihydropyrrole-1-carboxylate
  参考文献：
  名称：

  Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2S,5R)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside

  摘要：

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.

  DOI：

  10.1021/ol027268a

文献信息

• Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2<i>S</i>,5<i>R</i>)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside
  作者：Elias A. Severino、Edson R. Costenaro、Ariel L. L. Garcia、Carlos Roque D. Correia

  DOI：10.1021/ol027268a

  日期：2003.2.1

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.