4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenol | 169216-70-0

• 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: 4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenol
• CAS: 169216-70-0
• 化学式: C₁₆H₁₈O₂S
• 分子量: 274.384
• InChiKey: ZRBGZTXZKOITQT-UHFFFAOYSA-N

物化性质

• 沸点：
  475.3±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(Benzenesulfinyl)-2,3,5,6-tetramethylphenol 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.17h， 生成 杜醌
  参考文献：
  名称：

  Facile and Efficient Sulfenylation Method Using Quinone Mono-O,S-Acetals under Mild Conditions

  摘要：

  A novel sulfenylation method induced by aromatization of quinone mono-O,S-acetals is described. These sulfenylation reagents readily react with silyl enolethers or electron rich aromatic compounds to give sulfenylation products under mild conditions. In particular, O,S-acetal 2j, which possesses a pentafluorophenylthio function, is the most effective reagent from the standpoint of the adaptability for various substrates.

  DOI：

  10.1021/jo001710q
• 作为产物：
  描述：

  sodium benzenesulfonate 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氯化铝 、 氯化亚砜 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 4-(Benzenesulfinyl)-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

文献信息

• A novel efficient sulfenylation method using quinone mono-O,S-acetals under mild conditions
  作者：Masato Matsugi、Kentoku Gotanda、Kenji Murata、Yasuyuki Kita

  DOI：10.1039/a702912h

  日期：——

  A novel method for sulfenylation induced by aromatization of quinone mono-O,S-acetals is described.

  一种通过醌单-O,S-乙缩醛芳构化诱导硫醚化的新型方法被报道出来。
• An efficient synthesis of p-quinones utilizing a novel Pummerer-type rearrangement of p-sulfinylphenols
  作者：Shuji Akai、Yoshifumi Takeda、Kiyosei Iio、Yutaka Yoshida、Yasuyuki Kita

  DOI：10.1039/c39950001013

  日期：——

  Treatment of the p-sulfinylphenol derivatives 1 and 5 with trifluoroacetic anhydride causes a Pummerer-type rearrangement on aromatic rings and concomitant desulfurization to give 1 : 1 mixtures of the corresponding p-quinones and p-dihydroquinones, which are subjected to mild oxidation to provide high yields of p-quinones 3 and 7.

  对亚磺酰基苯酚衍生物 1 和 5 经三氟乙酸酐处理后，会在芳香环上发生普默尔型重排反应，同时发生脱硫反应，从而得到 1 : 1 的相应对醌和对二氢醌混合物。
• Some Recent Advances in Pummerer-type Reactions
  作者：Yasuyuki Kita

  DOI：10.1080/10426509708545516

  日期：1997.1.1

  first successful Pummerer-type reaction of the aromatic ring. In this review, we describe 1) the asymmetric Pummerer-type rearrangement induced by an O-silylated ketene acetal, 2) the asymmetric Pummerer-type rearrangement induced by an ethoxy vinyl acetate, 3) the additive-Pummerer-type reaction, 4) the asymmetric Pummerer-type cyclization induced by an O-silylated ketene acetal, and 5) the aromatic

  亚砜与酸酐的普默勒重排是合成 α 取代硫化物的有用方法，从合成和机械的角度来看都引起了相当大的关注。近年来，我们开发了两种新颖且重要的Pummerer型反应；i) 具有高度对映体过量的手性非外消旋亚砜的不对称 Pummerer 型反应，以及 ii) 芳香环的第一个成功的 Pummerer 型反应。在这篇综述中，我们描述了 1) 由 O-甲硅烷基化乙烯酮缩醛引起的不对称 Pummerer 型重排，2) 由乙氧基乙酸乙烯酯引起的不对称 Pummerer 型重排，3) 添加剂-Pummerer 型反应，4)由O-甲硅烷基化乙烯酮缩醛诱导的不对称Pummerer型环化，
• 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