N-(3,4-dimethoxyphenethyl)-N-benzylacetamide | 63283-39-6

• 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: N-(3,4-dimethoxyphenethyl)-N-benzylacetamide
• 英文别名: N-Acetyl-N-benzyl-3,4-dimethoxy-phenaethylamin；N-benzyl-N-[2-(3,4-dimethoxyphenyl)ethyl]acetamide
• CAS: 63283-39-6
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: ZCYMLAUUPLWSSJ-UHFFFAOYSA-N

物化性质

• 沸点：
  475.1±45.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxyphenethyl)-N-benzylacetamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到N-(3,4-dihydroxyphenethyl)-N-benzylacetamide
  参考文献：
  名称：

  Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine

  摘要：

  Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxyamphimedine and deoxyamphimedine. Oxidation of the latter using either K-3[Fe(CN)(6)] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyampbimedine and amphimedine.

  DOI：

  10.1021/acs.joc.5b02312
• 作为产物：
  描述：

  3,4-二甲氧基苯乙胺 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 N-(3,4-dimethoxyphenethyl)-N-benzylacetamide
  参考文献：
  名称：

  Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine

  摘要：

  Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxyamphimedine, deoxyamphimedine, and amphimedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxyamphimedine and deoxyamphimedine. Oxidation of the latter using either K-3[Fe(CN)(6)] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyampbimedine and amphimedine.

  DOI：

  10.1021/acs.joc.5b02312

文献信息

• Phosphorous pentoxide-pyridine: A new combination for Bischler-Napieralski reaction
  作者：Nobuo Itoh、Shigehiko Sugasawa

  DOI：10.1016/0040-4020(57)85009-1

  日期：1957.1

  The Bischler-Napieralski type of cyclisation can be effected by treating appropriately substituted acyl β-phenethylamides with phosphorous pentoxide in boiling pyridine. Isoquinolines can be recovered as the free base from the resultant pyridine layer; this reaction gives a good yield.

  Bischler-Napieralski型环化可通过在沸腾的吡啶中用五氧化二磷处理适当取代的酰基β-苯乙酰胺来实现。异喹啉可以作为游离碱从所得吡啶层中回收；参见图1。该反应产生良好的收率。