(4-(bis(ethylthio)methyl)-2-methoxyphenoxy)(tert-butyl)dimethylsilane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4-(bis(ethylthio)methyl)-2-methoxyphenoxy)(tert-butyl)dimethylsilane
• 英文别名: [4-[Bis(ethylsulfanyl)methyl]-2-methoxyphenoxy]-tert-butyl-dimethylsilane
• 化学式: C₁₈H₃₂O₂S₂Si
• 分子量: 372.668
• InChiKey: PHGKWDIZLNTFII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.58
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  O-tert-butyldimethylsilylvanillin 、 乙硫醇 在 [bmim]BF₄ 作用下， 反应 2.0h， 以85%的产率得到(4-(bis(ethylthio)methyl)-2-methoxyphenoxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Eco-friendly and Highly Chemoselective 1,3-Oxathio- and 1,3-Dithioacetalization of Aldehydes Using Ionic Liquids

  摘要：

  室温离子液体首次被用作新型且可回收的反应介质，用于在温和中性条件下将醛选择性转化为相应的1,3-氧硫杂环和二硫杂环衍生物，产率极佳。在这些反应条件下，包括TBDMS、PMB、THP、MOM、苄基、炔丙基醚、乙缩醛、氨基甲酸酯和酯等多种功能性和保护性官能团都能稳定存在。回收的活性离子液体可循环用于后续四到五次反应，活性保持一致。

  DOI：

  10.1246/cl.2003.672

文献信息

• Eco-friendly and Highly Chemoselective 1,3-Oxathio- and 1,3-Dithioacetalization of Aldehydes Using Ionic Liquids
  作者：J. S. Yadav、B. V. S. Reddy、G. Kondaji

  DOI：10.1246/cl.2003.672

  日期：2003.8

  Room temperature ionic liquids have been employed for the first time as novel and recyclable reaction media for the chemoselective conversion of aldehydes into their corresponding 1,3-oxathio- and dithioacetal derivatives in excellent yields under mild and neutral conditions. A wide range of functional and protecting groups such as TBDMS, PMB, THP, MOM, benzyl, propargyl ethers, acetonides, carbamates and esters are survived under these reaction conditions. The recovered activated ionic liquids can be recycled for four to five subsequent runs with consistency in activity.

  室温离子液体首次被用作新型且可回收的反应介质，用于在温和中性条件下将醛选择性转化为相应的1,3-氧硫杂环和二硫杂环衍生物，产率极佳。在这些反应条件下，包括TBDMS、PMB、THP、MOM、苄基、炔丙基醚、乙缩醛、氨基甲酸酯和酯等多种功能性和保护性官能团都能稳定存在。回收的活性离子液体可循环用于后续四到五次反应，活性保持一致。
• Hafnium Trifluoromethanesulfonate (Hafnium Triflate) as a Highly Efficient Catalyst for Chemoselective Thioacetalization and Transthioacetalization of Carbonyl Compounds
  作者：Yan-Chao Wu、Jieping Zhu

  DOI：10.1021/jo8021988

  日期：2008.12.5

  A range of carbonyl compounds including aliphatic and aromatic aldehydes and ketones were converted to the corresponding thioacetals in high yields in the presence of a catalytic amount of hafnium trifluoromethanesulfonate (0.1 mol %, room temperature), The mild conditions tolerated various sensitive functional and protecting groups and were racemization-free when applied to alpha-aminoaldehydes. Transacetalization and chemoselective thioacetalization of aromatic aldehydes in the presence of aliphatic aldehydes and ketones were also documented.