(S)-N-benzyl-3-(3,4-dimethoxyphenyl)-N-(4-methylpent-3-enyl)alaninol | 372965-66-7

• 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-benzyl-3-(3,4-dimethoxyphenyl)-N-(4-methylpent-3-enyl)alaninol
• CAS: 372965-66-7
• 化学式: C₂₄H₃₃NO₃
• 分子量: 383.531
• InChiKey: JPOWGEAPSPJNCF-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  28.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  41.93
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-N-benzyl-3-(3,4-dimethoxyphenyl)-N-(4-methylpent-3-enyl)alaninol 在 palladium on activated charcoal 草酰氯 、 4 A molecular sieve 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， -45.0~60.0 ℃ 、1.01 MPa 条件下， 反应 66.0h， 生成 (1S,4aS,10aS)-1-(3,4-dimethoxybenzyl)-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[b][1,7]naphthyridine
  参考文献：
  名称：

  Pictet-Spengler Cyclizationvs. Aminal Formation: Competing Reaction Pathways of Benzo[b][1,7]naphthyridines Controlled by the Configuration

  摘要：

  Diastereoisomeric benzo[b][1,7]naphthyridines 13a,b were synthesized in nine steps from L-DOPA employing a Lewis acid-catalyzed cyclization of N-(4-methylpent-3-enyl)-alpha -amino aldehydes as the key step. Under aprotic Pictet-Spengler conditions, compounds 13a,b undergo different reaction pathways depending on the relative configuration. Whereas trans,cis-diastereoisomer 13a yielded the desired Pictet-Spengler cyclization product albeit in very low yield, the corresponding concave-shaped all-cis-diastereoisomer 13b undergoes intramolecular aminal formation.

  DOI：

  10.1002/1522-2675(20010711)84:7<2064::aid-hlca2064>3.0.co;2-y
• 作为产物：
  描述：

  (S)-(+)-3,4-二甲氧基苯丙氨酸乙酯 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 potassium carbonate 、 calcium oxide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 196.0h， 生成 (S)-N-benzyl-3-(3,4-dimethoxyphenyl)-N-(4-methylpent-3-enyl)alaninol
  参考文献：
  名称：

  Pictet-Spengler Cyclizationvs. Aminal Formation: Competing Reaction Pathways of Benzo[b][1,7]naphthyridines Controlled by the Configuration

  摘要：

  Diastereoisomeric benzo[b][1,7]naphthyridines 13a,b were synthesized in nine steps from L-DOPA employing a Lewis acid-catalyzed cyclization of N-(4-methylpent-3-enyl)-alpha -amino aldehydes as the key step. Under aprotic Pictet-Spengler conditions, compounds 13a,b undergo different reaction pathways depending on the relative configuration. Whereas trans,cis-diastereoisomer 13a yielded the desired Pictet-Spengler cyclization product albeit in very low yield, the corresponding concave-shaped all-cis-diastereoisomer 13b undergoes intramolecular aminal formation.

  DOI：

  10.1002/1522-2675(20010711)84:7<2064::aid-hlca2064>3.0.co;2-y

文献信息

• Pictet-Spengler Cyclizationvs. Aminal Formation: Competing Reaction Pathways of Benzo[b][1,7]naphthyridines Controlled by the Configuration
  作者：Tim Dickner、Sabine Laschat

  DOI：10.1002/1522-2675(20010711)84:7<2064::aid-hlca2064>3.0.co;2-y

  日期：2001.7.11

  Diastereoisomeric benzo[b][1,7]naphthyridines 13a,b were synthesized in nine steps from L-DOPA employing a Lewis acid-catalyzed cyclization of N-(4-methylpent-3-enyl)-alpha -amino aldehydes as the key step. Under aprotic Pictet-Spengler conditions, compounds 13a,b undergo different reaction pathways depending on the relative configuration. Whereas trans,cis-diastereoisomer 13a yielded the desired Pictet-Spengler cyclization product albeit in very low yield, the corresponding concave-shaped all-cis-diastereoisomer 13b undergoes intramolecular aminal formation.