N-((E)-Buta-1,3-dienyl)-N-(4-methoxy-benzyl)-2-(4-methoxy-phenyl)-acetamide | 183311-41-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: N-((E)-Buta-1,3-dienyl)-N-(4-methoxy-benzyl)-2-(4-methoxy-phenyl)-acetamide
• CAS: 183311-41-3
• 化学式: C₂₁H₂₃NO₃
• 分子量: 337.419
• InChiKey: LVCGXMZKBWXXHA-LHHJGKSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  叔丁基二甲基氯硅烷 、 N-((E)-Buta-1,3-dienyl)-N-(4-methoxy-benzyl)-2-(4-methoxy-phenyl)-acetamide 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 ((E)-Buta-1,3-dienyl)-[(Z)-1-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-vinyl]-(4-methoxy-benzyl)-amine
  参考文献：
  名称：

  Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions

  摘要：

  We have studied the reactivity of the N,O-ketene N-1,3-butadienyl-N-alkyl-O-silyl acetals 1a-e with C-60 proceeding through a tandem process to give the adducts 2a-e, The addition order of these tandem reactions has been evaluated. The initial nucleophilic Michael-like addition of the electron-rich N,O-ketene acetal moiety proceeds unusually fast at 25 degrees C, followed by an intramolecularly accelerated Diels-Alder step that is highly diastereoselective. The structures of compounds 2a-e were determined from the H-1 and C-13 NMR shifts and from II-II coupling patterns, while their stereochemistry was deduced from 2D T-ROESY NMR experiments. The proposed mechanism for the nucleophilic addition involves single electron transfer followed by radical anion-radical cation recombination. Computational investigations of the reaction pathways, transition states, and conformational energies have been carried out to corroborate the experimental data.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3162::aid-chem3162>3.0.co;2-h
• 作为产物：
  描述：

  4-甲氧基苄胺 在 4 A molecular sieve 、 N,N-二乙基苯胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 4.0h， 生成 N-((E)-Buta-1,3-dienyl)-N-(4-methoxy-benzyl)-2-(4-methoxy-phenyl)-acetamide
  参考文献：
  名称：

  Preparation of N-Alkylketene-N-Butadienyl-N,O-Silyl Acetals

  摘要：

  描述了一系列二烯酰胺 5a-j 的合成，采用 Oppolzer 方法。通过 Rathke 方法，可以从相应的二烯胺中以良好的产率获得酮烯 N,O-硅醚 6a-j。这些酮烯醚不含碱和盐，可自由获得。它们稳定，可以在 -20°C 下存储。这些新型二烯是串联反应的有用试剂。

  DOI：

  10.1055/s-1996-4359

文献信息

• Preparation of N-Alkylketene-N-Butadienyl-N,O-Silyl Acetals
  作者：Andreas Franz、Pierre-Yves Eschler、Manuel Tharin、Helen Stoeckli-Evans、Reinhard Neier

  DOI：10.1055/s-1996-4359

  日期：1996.10

  The synthesis of a series of dienamides 5a-j using Oppolzer’s method is described. Using Rathke’s method the ketene N,O-silyl acetals 6a-j can be obtained in good yield from the corresponding dienamines. The ketene acetals are obtained free of base and free of salts. They are stable and can be stored at -20°C. The new dienes are useful reagents for tandem reactions.

  描述了一系列二烯酰胺 5a-j 的合成，采用 Oppolzer 方法。通过 Rathke 方法，可以从相应的二烯胺中以良好的产率获得酮烯 N,O-硅醚 6a-j。这些酮烯醚不含碱和盐，可自由获得。它们稳定，可以在 -20°C 下存储。这些新型二烯是串联反应的有用试剂。
• Tandem Nucleophilic Addition/Diels-Alder Reaction ofN-ButadienylN,O-Ketene Silyl Acetals with C60: Stereoselective Formation of Bicyclic Octahydroquinolino-1,2,3,4-Tetrahydrobuckminsterfullerenes and Combined NMR Spectroscopic and Computational Evaluation of the Functionalization Reactions
  作者：Yves Rubin、Padma S. Ganapathi、Andreas Franz、Yi-Zhong An、Wenyuan Qian、Reinhard Neier

  DOI：10.1002/(sici)1521-3765(19991105)5:11<3162::aid-chem3162>3.0.co;2-h

  日期：1999.11.5

  We have studied the reactivity of the N,O-ketene N-1,3-butadienyl-N-alkyl-O-silyl acetals 1a-e with C-60 proceeding through a tandem process to give the adducts 2a-e, The addition order of these tandem reactions has been evaluated. The initial nucleophilic Michael-like addition of the electron-rich N,O-ketene acetal moiety proceeds unusually fast at 25 degrees C, followed by an intramolecularly accelerated Diels-Alder step that is highly diastereoselective. The structures of compounds 2a-e were determined from the H-1 and C-13 NMR shifts and from II-II coupling patterns, while their stereochemistry was deduced from 2D T-ROESY NMR experiments. The proposed mechanism for the nucleophilic addition involves single electron transfer followed by radical anion-radical cation recombination. Computational investigations of the reaction pathways, transition states, and conformational energies have been carried out to corroborate the experimental data.