2,6-Bis(1,1-dimethylethyl)-4-methylphenyl 1-((1,1-dimethylethyl)dimethylsiloxy)cycloprop-1-ene-2-carboxylate | 172977-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 2,6-Bis(1,1-dimethylethyl)-4-methylphenyl 1-((1,1-dimethylethyl)dimethylsiloxy)cycloprop-1-ene-2-carboxylate
• 英文别名: (2,6-Ditert-butyl-4-methylphenyl) 2-[tert-butyl(dimethyl)silyl]oxycyclopropene-1-carboxylate
• CAS: 172977-68-3
• 化学式: C₂₅H₄₀O₃Si
• 分子量: 416.676
• InChiKey: GPGJSUPOGDADJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.18
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 2,6-Bis(1,1-dimethylethyl)-4-methylphenyl 1-((1,1-dimethylethyl)dimethylsiloxy)cycloprop-1-ene-2-carboxylate 在 盐酸 作用下， 反应 12.0h， 生成 2,6-Bis(1,1-dimethylethyl)-4-methylphenyl methyl ethane-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis and Chemistry of Donor/Acceptor-Substituted Cyclopropenes

  摘要：

  Rhodium(II) acetate, or trifluoroacetate-catalyzed decomposition of 1-diazo-2-(trialkylsiloxy)propenes with electron-withdrawing groups at the 1-position results in the formation of highly reactive cyclopropenes. These cyclopropenes contain both donor and acceptor substituents on the alkene and are very susceptible to ring opening and fragmentation reactions, Nevertheless, when appropriately functionalized with bulky substituents they can be of sufficient stability to be isolated and characterized.

  DOI：

  10.1021/jo00128a027
• 作为产物：
  描述：

  2,6-di-tert-butyl-4-methylphenyl diazoacetoacetate 在 dirhodium tetraacetate 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,6-Bis(1,1-dimethylethyl)-4-methylphenyl 1-((1,1-dimethylethyl)dimethylsiloxy)cycloprop-1-ene-2-carboxylate
  参考文献：
  名称：

  Synthesis and Chemistry of Donor/Acceptor-Substituted Cyclopropenes

  摘要：

  Rhodium(II) acetate, or trifluoroacetate-catalyzed decomposition of 1-diazo-2-(trialkylsiloxy)propenes with electron-withdrawing groups at the 1-position results in the formation of highly reactive cyclopropenes. These cyclopropenes contain both donor and acceptor substituents on the alkene and are very susceptible to ring opening and fragmentation reactions, Nevertheless, when appropriately functionalized with bulky substituents they can be of sufficient stability to be isolated and characterized.

  DOI：

  10.1021/jo00128a027

文献信息

• Unexpected Catalytic Reactions of Silyl-Protected Enol Diazoacetates with Nitrile Oxides That Form 5-Arylaminofuran-2(3<i>H</i>)-one-4-carboxylates
  作者：Xinfang Xu、Dmitry Shabashov、Peter Y. Zavalij、Michael P. Doyle

  DOI：10.1021/ol203331r

  日期：2012.2.3

  Silyl-protected enol diazoacetates undergo dirhodium(II)-catalyzed reactions with nitrile oxides to form acid-labile ketenimines via dipolar cycloaddition of nitrile oxides to a donor/acceptor cyclopropene and Lossen rearrangement of the dipolar adduct; acid catalysis converts the ketenimine to the furan product.
• Synthesis and Chemistry of Donor/Acceptor-Substituted Cyclopropenes
  作者：Huw M. L. Davies、Jeffrey H. Houser、Craig Thornley

  DOI：10.1021/jo00128a027

  日期：1995.11

  Rhodium(II) acetate, or trifluoroacetate-catalyzed decomposition of 1-diazo-2-(trialkylsiloxy)propenes with electron-withdrawing groups at the 1-position results in the formation of highly reactive cyclopropenes. These cyclopropenes contain both donor and acceptor substituents on the alkene and are very susceptible to ring opening and fragmentation reactions, Nevertheless, when appropriately functionalized with bulky substituents they can be of sufficient stability to be isolated and characterized.