1-(2-methoxyphenylthio)-3-(pyridin-3-yl)-2-naphthol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-methoxyphenylthio)-3-(pyridin-3-yl)-2-naphthol
• 英文别名: 1-(2-Methoxyphenyl)sulfanyl-3-pyridin-3-ylnaphthalen-2-ol；1-(2-methoxyphenyl)sulfanyl-3-pyridin-3-ylnaphthalen-2-ol
• 化学式: C₂₂H₁₇NO₂S
• 分子量: 359.448
• InChiKey: DQILBIVDCLMKJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  67.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲氧基萘-2-硼酸 在 吡啶 、 四(三苯基膦)钯 、 氢溴酸 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 1-(2-methoxyphenylthio)-3-(pyridin-3-yl)-2-naphthol
  参考文献：
  名称：

  Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols

  摘要：

  1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl)naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an easy to handle method to synthesize 1-arylthio-2-naphthols. It has been revealed that electron withdrawing groups on the aryl thiol promoted the yields and heterocycle substituents at the 3-position of the naphthalene core are tolerable by the reaction. This reaction can thus serve as a corner stone in the structural diversification of 3-heterocycle substituted 1-arylthio-2-naphthols as potential inhibitors of cytochrome P450. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.111

文献信息

• Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols
  作者：Cornelia M. Grombein、Qingzhong Hu、Ralf Heim、Volker Huch、Rolf W. Hartmann

  DOI：10.1016/j.tetlet.2013.09.111

  日期：2013.11

  1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl)naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an easy to handle method to synthesize 1-arylthio-2-naphthols. It has been revealed that electron withdrawing groups on the aryl thiol promoted the yields and heterocycle substituents at the 3-position of the naphthalene core are tolerable by the reaction. This reaction can thus serve as a corner stone in the structural diversification of 3-heterocycle substituted 1-arylthio-2-naphthols as potential inhibitors of cytochrome P450. (C) 2013 Elsevier Ltd. All rights reserved.