4-<<2-(methylamino)ethyl>thio>phenol | 143745-64-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-<<2-(methylamino)ethyl>thio>phenol
• 英文别名: 4-[2-(Methylamino)ethylsulfanyl]phenol
• CAS: 143745-64-6
• 化学式: C₉H₁₃NOS
• 分子量: 183.274
• InChiKey: QEMPSHBMNHQBJN-UHFFFAOYSA-N

物化性质

• 沸点：
  324.5±27.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-2-恶唑烷酮 、 4-羟基苯硫酚 在 lithium chloride 作用下， 以 neat (no solvent) 为溶剂， 以55%的产率得到4-<<2-(methylamino)ethyl>thio>phenol
  参考文献：
  名称：

  The use of 2-oxazolidinones as latent aziridine equivalents. 2. Aminoethylation of aromatic amines, phenols, and thiophenols

  摘要：

  The utility of 2-oxazolidinones 1 as latent, carboxylated aziridine functionalities was examined. Reaction of 2-oxazolidinone (1a), 3-methyl-2-oxazolidinone (1b), 3-(phenylmethyl)-2-oxazolidinone (1c), 3-phenyl-2-oxazolidinone (1d), 4,4-dimethyl-2-oxazolidinone (1e), and 5-ethyl-2-oxazolidinone (1f) with aromatic amine salts, phenol, or thiophenols at elevated temperatures (> 130-degrees-C) afforded aminoethylated adducts. The aminoethylation occurred with concomitant loss of carbon dioxide to furnish variously substituted N-aryl-1,2-ethanediamines 4, 1-(2-phenoxyethyl)-2-imidazolidinone (8), or 2-(arylthio)ethanamines 9 on reactions of 1 with aromatic amine salts, phenol, and thiophenols, respectively. Imidazolidinone 8 is believed to be a secondary reaction product resulting from the condensation of the initially formed 2-phenoxyethanamine with starting oxazolidinone 1a. The aminoethylation reaction did not proceed with aliphatic amine hydrochlorides or alkyl mercaptans. Preliminary mechanistic pathways for these ring openings were also investigated employing a specific, C-5 deuterium-labeled oxazolidinone 1b-d2. Ring-opening experiments of 1b-d2 with N-methylaniline hydrochloride suggest reaction can occur through either a dioxazolinium 5 and/or an aziridinium 6 intermediate. In contrast, reaction of 1b-d2 with thiophenol suggests ring-opening to proceed only via the dioxazolinium pathway.

  DOI：

  10.1021/jo00049a037