tert-Butyl-[3-(3,4-dimethoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane | 153993-01-2

• 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-[3-(3,4-dimethoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane
• 英文别名: Tert-butyl-[4-(3,4-dimethoxyphenyl)but-1-en-2-yloxy]-dimethylsilane
• CAS: 153993-01-2
• 化学式: C₁₈H₃₀O₃Si
• 分子量: 322.52
• InChiKey: AKXBUERQOGVGGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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-[3-(3,4-dimethoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane 在 萘-1,4-二腈 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以10%的产率得到4-(3,4-二甲氧基苯基)丁烷-2-酮
  参考文献：
  名称：

  甲硅烷基醚的分子内亲核加成反应到光敏电子转移（PET）生成的芳烃自由基阳离子上：一种基于非试剂的新型碳环化反应：

  摘要：

  通过向PET生成的芳烃自由基阳离子分子内添加甲硅烷基醚的新碳环化策略已被报道。

  DOI：

  10.1016/0040-4039(93)88123-z
• 作为产物：
  描述：

  4-(3,4-二甲氧基苯基)-3-丁烯-2-酮 在 palladium on activated charcoal 氢气 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.33h， 生成 tert-Butyl-[3-(3,4-dimethoxy-phenyl)-1-methylene-propoxy]-dimethyl-silane
  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

• Intramolecular nucleophilic addition of silylenol ether to photosensitized electron transfer (PET) generated arene radical cations: A novel non-reagent based carboannulation reaction:
  作者：Ganesh Pandey、A. Krishna、K. Girija、M. Karthikeyan

  DOI：10.1016/0040-4039(93)88123-z

  日期：1993.10

  A New carboannulation strategy by intramolecular addition of silylenol ether to PET generated arene radical cation is reported.

  通过向PET生成的芳烃自由基阳离子分子内添加甲硅烷基醚的新碳环化策略已被报道。
• 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.