Tert-butyl-dimethyl-(2,3,5,6-tetramethyl-4-methylsulfinylphenoxy)silane | 173069-09-5

• 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-dimethyl-(2,3,5,6-tetramethyl-4-methylsulfinylphenoxy)silane
• CAS: 173069-09-5
• 化学式: C₁₇H₃₀O₂SSi
• 分子量: 326.576
• InChiKey: BOAHELNKKFEKOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Tert-butyl-dimethyl-(2,3,5,6-tetramethyl-4-methylsulfinylphenoxy)silane 、 三氟乙酸酐 以 氯仿 为溶剂， 反应 0.5h， 以94%的产率得到
  参考文献：
  名称：

  Novel ipso-Substitution of p-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of p-Quinones and Protected p-Dihydroquinones

  摘要：

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.

  DOI：

  10.1021/jo970418o
• 作为产物：
  描述：

  2,3,5,6-四甲基苯酚 在 咪唑 、 三氯化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 Tert-butyl-dimethyl-(2,3,5,6-tetramethyl-4-methylsulfinylphenoxy)silane
  参考文献：
  名称：

  Novel ipso-Substitution of p-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of p-Quinones and Protected p-Dihydroquinones

  摘要：

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.

  DOI：

  10.1021/jo970418o

文献信息

• Pummerer-type rearrangement on aromatic rings: an unprecedented ipso-substitution of the sulfinyl group of p-sulfinylphenyl ethers into oxygen functional groups leading to protected dihydroquinone derivatives
  作者：Shuji Akai、Kiyosei Iio、Yoshifumi Takeda、Hiroshi Ueno、Kayoko Yokogawa、Yasuyuki Kita

  DOI：10.1039/c39950002319

  日期：——

  The treatment of p-(phenylsulfinyl)phenyl ethers 1 with trifluoroacetic anhydride in the presence of styrene selectively caused the direct ipso-substitution of the sulfinyl groups by trifluoroacetoxy groups, giving the protected dihydroquinone derivatives 3 in high to quantitative yields.

  在苯乙烯存在下，用三氟乙酸酐处理对(苯亚磺酰基)苯基醚 1，可选择性地使亚磺酰基直接被三氟乙酰氧基取代，从而得到高产率至定量的受保护二氢醌衍生物 3。
• Novel <i>ipso</i>-Substitution of <i>p</i>-Sulfinylphenols through the Pummerer-Type Reaction:  A Selective and Efficient Synthesis of <i>p</i>-Quinones and Protected <i>p</i>-Dihydroquinones
  作者：Shuji Akai、Yoshifumi Takeda、Kiyosei Iio、Kenji Takahashi、Nobuhisa Fukuda、Yasuyuki Kita

  DOI：10.1021/jo970418o

  日期：1997.8.1

  The treatment of p-sulfinylphenols 3a-q with trifluoroacetic anhydride caused a Pummerer-type reaction on aromatic rings and concomitant desulfurization to give mixtures of the corresponding p-dihydroquinones 9 and p-quinones 10, which were subsequently oxidized under mild conditions to provide high yields of p-quinones 10. On the other hand, the treatment of p-(phenylsulfinyl)-phenyl ethers 6 with trifluoroacetic anhydride in the presence of styrene caused the direct ipso-substitution of the sulfinyl groups into trifluoroacetoxy groups, giving the protected dihydroquinones 14 in high yields. Both types of reactions were generally completed below room temperature within 1 h and compatible with various functional groups such as the allyl, carbonyl, ester, amide, and silyloxy groups. The preparation of the p-sulfinylphenols 3 and the silyl ethers 6 is also described through p-specific thiocyanation of phenols followed by the Grignard reaction and oxidation.