[4-Hydroxy-3-(3-hydroxypropyl)-2,5,6-trimethylphenyl] thiocyanate | 196944-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: [4-Hydroxy-3-(3-hydroxypropyl)-2,5,6-trimethylphenyl] thiocyanate
• CAS: 196944-53-3
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: LSAQIMQFZHHCMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-Hydroxy-3-(3-hydroxypropyl)-2,5,6-trimethylphenyl] thiocyanate 生成 tert-Butyl-dimethyl-{2,3,5-trimethyl-6-[3-(tetrahydro-pyran-2-yloxy)-propyl]-4-thiocyanato-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
• 作为产物：
  描述：

  2-(3-Hydroxypropyl)-3,5,6-trimethylphenol 、 lead(II) thiocyanate 在 (二氯碘)-苯 作用下， 生成 [4-Hydroxy-3-(3-hydroxypropyl)-2,5,6-trimethylphenyl] thiocyanate
  参考文献：
  名称：

  An Efficient p-Thiocyanation of Phenols and Naphthols Using a Reagent Combination of Phenyliodine Dichloride and Lead(II) Thiocyanate.

  摘要：

  PhICl2 和 Pb(SCN)2 的组合可有效地对各种类型的对未取代苯酚和萘酚 1 进行对选择性硫氰酸化，从而得到对硫氰酸苯酚和萘酚 3。反应在 0°C 至室温下进行，产率高至定量。文中给出了 25 个例子，表明氯基、烯丙基、羰基、酯基、酰胺基和伯羟基等各种官能团与该反应相容。

  DOI：

  10.1248/cpb.45.1887