[4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenyl] acetate | 173069-04-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenyl] acetate
• CAS: 173069-04-0
• 化学式: C₁₈H₂₀O₃S
• 分子量: 316.421
• InChiKey: OHXMXYRZEFWCLK-UHFFFAOYSA-N

物化性质

• 沸点：
  469.9±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenyl] acetate 在 三氟乙酸酐 作用下， 以 氘代氯仿 为溶剂， 反应 48.0h， 以10%的产率得到(2,3,5,6-tetramethyl-4-phenylsulfanylphenyl) acetate
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1039/c39950002319
• 作为产物：
  描述：

  苯亚磺酰氯 在 三氯化铝 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 [4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenyl] acetate
  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

• Isolation of the Quinone MonoO,S-Acetal Intermediates of the Aromatic Pummerer-Type Rearrangement ofp-Sulfinylphenols with 1-Ethoxyvinyl Esters
  作者：Yasuyuki Kita、Yoshifumi Tekeda、Masato Matsugi、Kiyosei Iio、Kentoku Gotanda、Kenji Murata、Shuji Akai

  DOI：10.1002/anie.199715291

  日期：1997.8.4