2-[(4-methylphenyl)sulfonyl]-1-naphthol | 108980-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[(4-methylphenyl)sulfonyl]-1-naphthol
• 英文别名: 2-[(4-methylphenyl)sulfonyl]naphthalen-1-ol；p-Tolyl-(1-hydroxy-naphth-2-yl)-sulfon；2-[(4-Methylphenyl) sulfonyl]-1-naphthol；2-(4-methylphenyl)sulfonylnaphthalen-1-ol
• CAS: 108980-60-5
• 化学式: C₁₇H₁₄O₃S
• 分子量: 298.362
• InChiKey: ATUMGJBYBVJPKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-naphthyl tosylate 以 氯仿 为溶剂， 反应 0.12h， 以78%的产率得到2-[(4-methylphenyl)sulfonyl]-1-naphthol
  参考文献：
  名称：

  Thia-Fries rearrangement of aryl sulfonates in dry media under microwave activation

  摘要：

  An AlCl3-ZnCl2 mixture supported on silica gel is found to be a new efficient medium for the thia-Fries rearrangement of aryl sulfonates in solvent-free conditions under microwave dielectric heating. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00402-0

文献信息

• Graphite/Methanesulfonic Acid (GMA) as a New Reagent for Sulfonylation of Phenols and Thia-Fries Rearrangement of Aryl Sulfonates to Sulfonylphenols
  作者：Hashem Sharghi、Zahra Shahsavari-Fard

  DOI：10.1002/hlca.200490295

  日期：2005.1

  A new facile method for direct sulfonylation of phenols was developed. Graphite in methanesulfonic acid (GMA) was used to prepare sulfonylphenols by sulfonylation of phenol and naphthalene derivatives with p-toluenesulfonic acid (=4-methylbenzenesulfonic acid) (Table 1) and the thia-Fries rearrangement of aryl sulfonates (Table 4). Mechanistic studies showed that the sulfonylation reaction of phenols

  开发了一种新的直接苯酚磺酰化的简便方法。使用甲磺酸中的石墨（GMA）通过苯酚和萘衍生物与对甲苯磺酸（= 4-甲基苯磺酸）（表1）进行磺酰化以及芳基磺酸盐的硫-弗里斯重排（表4）来制备磺酰基苯酚。机理研究表明，GMA中苯酚的磺酰化反应是通过最初的磺酸盐形成，然后通过分子间机理使芳基磺酸盐的硫-弗里斯重排而发生的（方案3）。
• Al₂O₃/MeSO₃H (AMA) as a New Reagent for the Thia-Fries Rearrangement of Arylsulfonates to Hydroxyaryl Sulfones
  作者：Hashem Sharghi、Zahra Shahsavari-Fard

  DOI：10.1080/104265090929878

  日期：2005.11.1

  A new facile method for this-Fries rearrangement of arylsulfonates has been developed. A variety of arylsulfonates rearrange in excellent yields in the presence of Al2O3/MeSO3H as a new reagent without the use of any solvent.
• Thia-Fries rearrangement of aryl sulfonates in dry media under microwave activation
  作者：Firouz Matloubi Moghaddam、Mohammad G. Dakamin

  DOI：10.1016/s0040-4039(00)00402-0

  日期：2000.4

  An AlCl3-ZnCl2 mixture supported on silica gel is found to be a new efficient medium for the thia-Fries rearrangement of aryl sulfonates in solvent-free conditions under microwave dielectric heating. (C) 2000 Elsevier Science Ltd. All rights reserved.