tert-Butyl-dimethyl-[2,3,5,6-tetramethyl-4-(2-methyl-propane-2-sulfinyl)-phenoxy]-silane | 173069-08-4

• 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-(2-methyl-propane-2-sulfinyl)-phenoxy]-silane
• 英文别名: tert-butyl-(4-tert-butylsulfinyl-2,3,5,6-tetramethylphenoxy)-dimethylsilane
• CAS: 173069-08-4
• 化学式: C₂₀H₃₆O₂SSi
• 分子量: 368.656
• InChiKey: HJMDWDXZBNYKRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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-(2-methyl-propane-2-sulfinyl)-phenoxy]-silane 在 四丁基氟化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 6.0h， 生成 4-Tert-butylsulfinyl-2,3,5,6-tetramethylphenol
  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：

  tert-Butyl-(4-tert-butylsulfanyl-2,3,5,6-tetramethyl-phenoxy)-dimethyl-silane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 tert-Butyl-dimethyl-[2,3,5,6-tetramethyl-4-(2-methyl-propane-2-sulfinyl)-phenoxy]-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。