((E)-Buta-1,3-dienyl)-[(Z)-1-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-vinyl]-(4-methoxy-benzyl)-amine | 183311-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ((E)-Buta-1,3-dienyl)-[(Z)-1-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-vinyl]-(4-methoxy-benzyl)-amine
• 英文别名: (1E)-N-[(Z)-1-[tert-butyl(dimethyl)silyl]oxy-2-(4-methoxyphenyl)ethenyl]-N-[(4-methoxyphenyl)methyl]buta-1,3-dien-1-amine
• CAS: 183311-45-7
• 化学式: C₂₇H₃₇NO₃Si
• 分子量: 451.681
• InChiKey: LXHVEHOLOGGGJA-WQOBLJCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.23
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  足球烯 、 ((E)-Buta-1,3-dienyl)-[(Z)-1-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-vinyl]-(4-methoxy-benzyl)-amine 以 甲苯 为溶剂， 以22%的产率得到
  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-甲氧基苯乙酰氯 在 六甲基磷酰三胺 、 N,N-二乙基苯胺 、 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

文献信息

• 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.