1-Chloro-1-phenylsilinan-4-one | 1558028-46-8

• 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: 1-Chloro-1-phenylsilinan-4-one
• 英文别名: 1-chloro-1-phenylsilinan-4-one
• CAS: 1558028-46-8
• 化学式: C₁₁H₁₃ClOSi
• 分子量: 224.762
• InChiKey: HRQMEBZJPOYUGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 盐酸 、 9-硼双环[3.3.1]壬烷 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 1-Chloro-1-phenylsilinan-4-one
  参考文献：
  名称：

  Synthesis of 4-Silacyclohexan-1-ones and (4-Silacyclohexan-1-yl)amines Containing the Silicon Protecting Groups MOP (4-Methoxyphenyl), DMOP (2,4-Dimethoxyphenyl), or TMOP (2,4,6-Trimethoxyphenyl): Versatile Si- and C-Functional Building Blocks for Synthesis

  摘要：

  The 4-silacyclohexanones 1-6 were prepared in convenient multistep syntheses, starting from MeSi(OMe)(3) and PhSi(OMe)(3), respectively. Cleavage of the 4-methoxyphenyl (MOP), 2,6-dimethoxyphenyl (DMOP), and 2,4,6-trimethoxyphenyl (TMOP) protecting groups of 4-6 by treatment with HCl/Et2O in CH2Cl2 at 20 degrees C gives the 4-chloro-4-silacyclohexanone 13. Reductive amination of 1-6 with NH3 or i-PrNH2 yields the respective (4-silacyclohexan-1-yl)amines 7-12. Compounds 1-12 and all new precursors synthesized were characterized by elemental analyses (C, H, N) or mass spectrometric investigations (ESI-HRMS) and by NMR spectroscopic studies (H-1, C-13, Si-29). Compounds 1, 3, 5, and 6 and the precursors (MeO)(2)SiPh-(TMOP) (21) and (CH2=CH)(2)SiPh(TMOP) (27) were additionally characterized by single-crystal X-ray diffraction. Compounds 1-12 with their Si- and C-functional groups represent versatile building blocks for synthesis.

  DOI：

  10.1021/om401208y

文献信息

• Synthesis of 4-Silacyclohexan-1-ones and (4-Silacyclohexan-1-yl)amines Containing the Silicon Protecting Groups MOP (4-Methoxyphenyl), DMOP (2,4-Dimethoxyphenyl), or TMOP (2,4,6-Trimethoxyphenyl): Versatile Si- and C-Functional Building Blocks for Synthesis
  作者：Markus Fischer、Christian Burschka、Reinhold Tacke

  DOI：10.1021/om401208y

  日期：2014.2.24

  The 4-silacyclohexanones 1-6 were prepared in convenient multistep syntheses, starting from MeSi(OMe)(3) and PhSi(OMe)(3), respectively. Cleavage of the 4-methoxyphenyl (MOP), 2,6-dimethoxyphenyl (DMOP), and 2,4,6-trimethoxyphenyl (TMOP) protecting groups of 4-6 by treatment with HCl/Et2O in CH2Cl2 at 20 degrees C gives the 4-chloro-4-silacyclohexanone 13. Reductive amination of 1-6 with NH3 or i-PrNH2 yields the respective (4-silacyclohexan-1-yl)amines 7-12. Compounds 1-12 and all new precursors synthesized were characterized by elemental analyses (C, H, N) or mass spectrometric investigations (ESI-HRMS) and by NMR spectroscopic studies (H-1, C-13, Si-29). Compounds 1, 3, 5, and 6 and the precursors (MeO)(2)SiPh-(TMOP) (21) and (CH2=CH)(2)SiPh(TMOP) (27) were additionally characterized by single-crystal X-ray diffraction. Compounds 1-12 with their Si- and C-functional groups represent versatile building blocks for synthesis.