3,4-Bis-(dimethyl-phenyl-silanyl)-cyclobut-3-ene-1,2-dione | 181211-81-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3,4-Bis-(dimethyl-phenyl-silanyl)-cyclobut-3-ene-1,2-dione
• 英文别名: 3,4-Bis[dimethyl(phenyl)silyl]cyclobut-3-ene-1,2-dione
• CAS: 181211-81-4
• 化学式: C₂₀H₂₂O₂Si₂
• 分子量: 350.564
• InChiKey: ODGZVKZOXDFQEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-Bis-(dimethyl-phenyl-silanyl)-cyclobut-3-ene-1,2-dione 以 氘代氯仿 为溶剂， 反应 2.0h， 生成 2,3-Bis-(dimethyl-phenyl-silanyl)-buta-1,3-diene-1,4-dione
  参考文献：
  名称：

  Phenyldimethylsilyl-Substituted Ketenes and Bisketenes

  摘要：

  The phenyldimethylsilyl-substituted monoketene PhMe(2)SiCH=C=O (1) and bisketene (PhMe(2)SiC=C=O)(2) (3) have been prepared and compared to the corresponding Me(3)Si- and t-BuMe(2)Si-substituted species. The C-13, O-17, and Si-29 NMR spectra fit the pattern shown by other silylketenes and provide no evidence for transmission of a substituent effect of the Ph group through the silicon to the ketenyl group, as has been proposed for PhMe(2)Si-substituted radicals. The UV spectrum of 1 does show a longer lambda and greater epsilon than for t-BuMe(2)SiCH=C=O, and this may indicate some interaction of the phenyl group with the ketene chromophore, while the greater reactivity of 1 in hydration compared to t-BuMe(2)SiCH=C=O is ascribed to the inductive effect of the phenyl. The very similar ring-opening reactivity of the bis(phenyldimethylsilyl)cyclobutenedione (6) to form 3 compared to the bis(Me(3)Si) analogues also provides no evidence of a significant interaction of the phenyl with the ketene. A new type of stabilized 1,8-bisketene based on the arylbis(dimethylsilyl) grouping, namely, 1,4-bis(ketenyldimethylsilyl)benzene (12), has been prepared for the first time.

  DOI：

  10.1021/jo9605197
• 作为产物：
  描述：

  bis(phenyldimethylsilyl)acetylene 在 silver trifluoroacetate 、 锌 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 73.5h， 生成 3,4-Bis-(dimethyl-phenyl-silanyl)-cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Phenyldimethylsilyl-Substituted Ketenes and Bisketenes

  摘要：

  The phenyldimethylsilyl-substituted monoketene PhMe(2)SiCH=C=O (1) and bisketene (PhMe(2)SiC=C=O)(2) (3) have been prepared and compared to the corresponding Me(3)Si- and t-BuMe(2)Si-substituted species. The C-13, O-17, and Si-29 NMR spectra fit the pattern shown by other silylketenes and provide no evidence for transmission of a substituent effect of the Ph group through the silicon to the ketenyl group, as has been proposed for PhMe(2)Si-substituted radicals. The UV spectrum of 1 does show a longer lambda and greater epsilon than for t-BuMe(2)SiCH=C=O, and this may indicate some interaction of the phenyl group with the ketene chromophore, while the greater reactivity of 1 in hydration compared to t-BuMe(2)SiCH=C=O is ascribed to the inductive effect of the phenyl. The very similar ring-opening reactivity of the bis(phenyldimethylsilyl)cyclobutenedione (6) to form 3 compared to the bis(Me(3)Si) analogues also provides no evidence of a significant interaction of the phenyl with the ketene. A new type of stabilized 1,8-bisketene based on the arylbis(dimethylsilyl) grouping, namely, 1,4-bis(ketenyldimethylsilyl)benzene (12), has been prepared for the first time.

  DOI：

  10.1021/jo9605197

文献信息

• Phenyldimethylsilyl-Substituted Ketenes and Bisketenes
  作者：Ronghau Liu、Romeo M. Marra、Thomas T. Tidwell

  DOI：10.1021/jo9605197

  日期：1996.1.1

  The phenyldimethylsilyl-substituted monoketene PhMe(2)SiCH=C=O (1) and bisketene (PhMe(2)SiC=C=O)(2) (3) have been prepared and compared to the corresponding Me(3)Si- and t-BuMe(2)Si-substituted species. The C-13, O-17, and Si-29 NMR spectra fit the pattern shown by other silylketenes and provide no evidence for transmission of a substituent effect of the Ph group through the silicon to the ketenyl group, as has been proposed for PhMe(2)Si-substituted radicals. The UV spectrum of 1 does show a longer lambda and greater epsilon than for t-BuMe(2)SiCH=C=O, and this may indicate some interaction of the phenyl group with the ketene chromophore, while the greater reactivity of 1 in hydration compared to t-BuMe(2)SiCH=C=O is ascribed to the inductive effect of the phenyl. The very similar ring-opening reactivity of the bis(phenyldimethylsilyl)cyclobutenedione (6) to form 3 compared to the bis(Me(3)Si) analogues also provides no evidence of a significant interaction of the phenyl with the ketene. A new type of stabilized 1,8-bisketene based on the arylbis(dimethylsilyl) grouping, namely, 1,4-bis(ketenyldimethylsilyl)benzene (12), has been prepared for the first time.