tert-butyl-[(Z)-5-(3,4-dimethoxyphenyl)pent-2-en-2-yl]oxy-dimethylsilane | 153993-03-4

• 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: tert-butyl-[(Z)-5-(3,4-dimethoxyphenyl)pent-2-en-2-yl]oxy-dimethylsilane
• CAS: 153993-03-4
• 化学式: C₁₉H₃₂O₃Si
• 分子量: 336.547
• InChiKey: FVGMAFNNMFSBCF-GDNBJRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(Z)-5-(3,4-dimethoxyphenyl)pent-2-en-2-yl]oxy-dimethylsilane 在 萘-1,4-二腈 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 3.33h， 生成 2,3-dimethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-6-one
  参考文献：
  名称：

  New Intramolecular α-Arylation Strategy of Ketones by the Reaction of Silyl Enol Ethers to Photosensitized Electron Transfer Generated Arene Radical Cations:  Construction of Benzannulated and Benzospiroannulated Compounds

  摘要：

  Efficient intramolecular alpha-arylation of ketones is achieved by the reaction of silyl enol ethers to photosensitized electron transfer (PET) generated arene radical cations. The arene radical cations are generated by one-electron transfer from the excited state of the methoxy-substituted arenes to ground-state 1,4-dicyanonaphthalene (DCN). This arylation strategy has provided the unique opportunity of constructing five- (23), six- (18), seven- (25) and eight-membered (27) benzannulated as well as benzospiroannulated (34) compounds. The explanation for the formation of 27 has been advanced by considering the proximity between the arene radical cation and silyl enol ether due to the self-coiling in the aqueous environment.

  DOI：

  10.1021/jo9718612
• 作为产物：
  描述：

  Tert-butyl-[5-(3,4-dimethoxyphenyl)pent-1-en-2-yloxy]-dimethylsilane 在 咪唑 、 萘-1,4-二腈 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 48.0h， 生成 tert-butyl-[(Z)-5-(3,4-dimethoxyphenyl)pent-2-en-2-yl]oxy-dimethylsilane
  参考文献：
  名称：

  New Intramolecular α-Arylation Strategy of Ketones by the Reaction of Silyl Enol Ethers to Photosensitized Electron Transfer Generated Arene Radical Cations:  Construction of Benzannulated and Benzospiroannulated Compounds

  摘要：

  Efficient intramolecular alpha-arylation of ketones is achieved by the reaction of silyl enol ethers to photosensitized electron transfer (PET) generated arene radical cations. The arene radical cations are generated by one-electron transfer from the excited state of the methoxy-substituted arenes to ground-state 1,4-dicyanonaphthalene (DCN). This arylation strategy has provided the unique opportunity of constructing five- (23), six- (18), seven- (25) and eight-membered (27) benzannulated as well as benzospiroannulated (34) compounds. The explanation for the formation of 27 has been advanced by considering the proximity between the arene radical cation and silyl enol ether due to the self-coiling in the aqueous environment.

  DOI：

  10.1021/jo9718612

文献信息

• New Intramolecular α-Arylation Strategy of Ketones by the Reaction of Silyl Enol Ethers to Photosensitized Electron Transfer Generated Arene Radical Cations:  Construction of Benzannulated and Benzospiroannulated Compounds
  作者：Ganesh Pandey、M. Karthikeyan、A. Murugan

  DOI：10.1021/jo9718612

  日期：1998.5.1

  Efficient intramolecular alpha-arylation of ketones is achieved by the reaction of silyl enol ethers to photosensitized electron transfer (PET) generated arene radical cations. The arene radical cations are generated by one-electron transfer from the excited state of the methoxy-substituted arenes to ground-state 1,4-dicyanonaphthalene (DCN). This arylation strategy has provided the unique opportunity of constructing five- (23), six- (18), seven- (25) and eight-membered (27) benzannulated as well as benzospiroannulated (34) compounds. The explanation for the formation of 27 has been advanced by considering the proximity between the arene radical cation and silyl enol ether due to the self-coiling in the aqueous environment.