(S)-(-)-N-[2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]-4-oxopentanamide | 872516-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(-)-N-[2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]-4-oxopentanamide
• 英文别名: N-[(2S)-1-(3,4-dimethoxyphenyl)-3-hydroxypropan-2-yl]-4-oxopentanamide
• CAS: 872516-24-0
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: DEKDOFFOUFMQBB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(-)-N-[2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]-4-oxopentanamide 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (5S,10bS)-5-(hydroxymethyl)-10b-methyl-8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3-one 、 (5S,10bR)-5-(hydroxymethyl)-10b-methyl-8,9-dimethoxy-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-3-one
  参考文献：
  名称：

  Diastereoselective Intramolecular α-Amidoalkylation Reactions of l-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinolines

  摘要：

  Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).

  DOI：

  10.1021/jo051584w
• 作为产物：
  描述：

  methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(3,4-dimethoxyphenyl)propanoate 在 咪唑 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 sodium acetate 、 乙酸酐 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 44.5h， 生成 (S)-(-)-N-[2-(3,4-dimethoxyphenyl)-1-(hydroxymethyl)ethyl]-4-oxopentanamide
  参考文献：
  名称：

  Diastereoselective Intramolecular α-Amidoalkylation Reactions of l-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-a]isoquinolines

  摘要：

  Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).

  DOI：

  10.1021/jo051584w

文献信息

• Diastereoselective Intramolecular α-Amidoalkylation Reactions of <scp>l</scp>-DOPA Derivatives. Asymmetric Synthesis of Pyrrolo[2,1-<i>a</i>]isoquinolines
  作者：Eva García、Sonia Arrasate、Esther Lete、Nuria Sotomayor

  DOI：10.1021/jo051584w

  日期：2005.12.1

  Stereocontrolled intramolecular alpha-amidoalkylation reactions of L-DOPA-derived succinimides have been studied. Addition of MeLi to nonracemic succinimides 9a-d yields oxoamides, which are cyclized upon treatment with Lewis or protic acids to afford (5S, 10bS)-trans 11 or (5S,10bR)-cis 12 pyrroloisoquinolines with variable diastereoselectivities, but with high enantiomerical purities (ee 99%).