2-methyl-6-(methylsulfenyl)phenol | 25674-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-methyl-6-(methylsulfenyl)phenol
• 英文别名: 6-Methylmercapto-2-methyl-phenol；2-Metiltio-6-metil-fenolo；2-Methyl-6-(methylthio)phenol；2-methyl-6-methylsulfanylphenol
• CAS: 25674-55-9
• 化学式: C₈H₁₀OS
• mdl: MFCD16999039
• 分子量: 154.233
• InChiKey: MRCQDFNEMYBGIV-UHFFFAOYSA-N

物化性质

• 沸点：
  110-112 °C(Press: 18 Torr)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-6-(methylsulfenyl)phenol 在 四甲基乙二胺 、 仲丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 10.5h， 生成 N,N-diethyl-2-(2-hydroxy-3-methylphenyl)sulfanylacetamide
  参考文献：
  名称：

  定向金属化在合成中的应用。第6部分：在定向金属化条件下导致异环化的新型阴离子重排

  摘要：

  描述了由容易获得的酚的短而有效的合成缩合的1，4-氧杂噻吩-2-酮。该合成过程中的关键步骤是在定向金属化条件下迄今未报道的阴离子重排。重排由甲基硫烷基的侧链的去质子化之后发生ø -氨基甲酸酯定向组金属化而得，并且将反应混合物在室温下保持8-12小时。重排产物的酸介导的环化作用提供[1,4]草苷-2-一。

  DOI：

  10.1016/j.tet.2004.04.033
• 作为产物：
  描述：

  2-甲基-6-硝基苯酚 在 镍 sodium hydroxide 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-methyl-6-(methylsulfenyl)phenol
  参考文献：
  名称：

  Cabiddu,S. et al., Gazzetta Chimica Italiana, 1969, vol. 99, p. 1095 - 1106

  摘要：

  DOI：

文献信息

• Synthetic Routes to Polyheteroacenes:  Characterization of a Heterocyclic Ladder Polymer Containing Phenoxathiinium-type Building Blocks
  作者：Kenichi Oyaizu、Takefumi Mikami、Fumio Mitsuhashi、Eishun Tsuchida

  DOI：10.1021/ma010961d

  日期：2002.1.1

  The synthetic routes to ladder polymers that consist of benzenetetrayl subunits with oxo and methylsulfonio linkages are described. As the key intermediate, poly(phenylene oxide)s having pendant methylsulfenyl groups are prepared by copper-catalyzed oxidative polymerization of the corresponding phenols with O-2. The oxidation of the polymer with an equimolar amount of H2O2 in the presence of acetic acid effects the high-yielding conversion of methylsulfenyl to methylsulfinyl groups without the formation of the undesired methylsulfonyl groups. The superacidified condensation of the resulting polymer (Swern reaction of aryl sulfoxides) under dilution conditions induces the polymer-analogous intramolecular electrophilic ring-closing reaction of the hydroxymethylphenylsulfonium cation onto the adjacent benzene ring to yield the required ladder polymer, which has proved to be a semiconductor with an intrinsic electric conductivity of 2 x 10(-5) S/cm. A comparison of the spectroscopic properties of the ladder polymer with those of the model compounds such as 5-methylphenoxathiinium triflate and phenoxathiin discloses pi -electron delocalization over the methylsulfonio linkages, demonstrating the efficacy of the ladderization for p-pi /d-pi interactions in arylsulfonium moieties. This synthetic approach permits the thio and alkylsulfonio ladder linkages for a variety of phenyl ethers to form in high yields.
• Alkylthiolation of Phenols
  作者：Paul F. Ranken、B. Gary Mckinnie

  DOI：10.1055/s-1984-30744

  日期：——
• RANKEN, P. F.;MCKINNIE, B. G., SYNTHESIS, BRD, 1984, N 2, 117-119
  作者：RANKEN, P. F.、MCKINNIE, B. G.

  DOI：——

  日期：——
• Application of directed metalation in synthesis. Part 6: A novel anionic rearrangement under directed metalation conditions leading to heteroannulation
  作者：Tarun Kanti Pradhan、Chandrani Mukherjee、Sukanta Kamila、Asish De

  DOI：10.1016/j.tet.2004.04.033

  日期：2004.6

  from easily available phenols is described. The key step in this synthesis is a hitherto unreported anionic rearrangement under directed metalation conditions. The rearrangement occurs after side chain deprotonation of a methyl sulfanyl group by an O-carbamate directed metalating group and the reaction mixture is kept at room temperature for 8–12 h. Acid-mediated cyclisation of the rearranged product

  描述了由容易获得的酚的短而有效的合成缩合的1，4-氧杂噻吩-2-酮。该合成过程中的关键步骤是在定向金属化条件下迄今未报道的阴离子重排。重排由甲基硫烷基的侧链的去质子化之后发生ø -氨基甲酸酯定向组金属化而得，并且将反应混合物在室温下保持8-12小时。重排产物的酸介导的环化作用提供[1,4]草苷-2-一。
• Cabiddu,S. et al., Gazzetta Chimica Italiana, 1969, vol. 99, p. 1095 - 1106
  作者：Cabiddu,S. et al.

  DOI：——

  日期：——