2,2,-dimethyl-3-phenoxythietane | 647033-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2,-dimethyl-3-phenoxythietane
• 英文别名: Thietane, 2,2-dimethyl-3-phenoxy-；2,2-dimethyl-3-phenoxythietane
• CAS: 647033-00-9
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: FXCKQBMDYNVJGU-UHFFFAOYSA-N

物化性质

• 沸点：
  279.8±33.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  sodium phenoxide 、 2,2-dimethyl-3-(chloromethyl)thiirane 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 bis(3-methyl-2-buten-1-yl)disulfide 、 2,2,-dimethyl-3-phenoxythietane
  参考文献：
  名称：

  摘要：

  (alpha-Chloroalkyl)thiiranes react with sodium phenolates at heating in water-alcohol mixtures furnishing phenoxymethylthiiranes, 3-phenoxythietanes (resulting from thiirane-thietane rearrangement), or their mixture. The increased polarity of solvent favors the thiirane-thietane rearrangement. 2,2-Dimethyl-3-(chloromethyl)thiirane forms an exclusion for it does not afford (phenoxymethyl)thiirane even in anhydrous ethanol. Diastereomeric erythro- and threo-(1-chloroethyl)thiiranes react stereospecifically giving 2-methyl-3-phenoxymethylthiiranes or 2-methyl-3-phenoxythietanes of trans- and cis-configuration respectively. Specific features of these reactions are discussed from the viewpoint of solvent polarity effect on the competition between formal chlorine substitution along "recyclization" mechanism or through thiirane-thietane rearrangement.

  DOI：

  10.1023/a:1025592320130

文献信息

• ——
  作者：A. A. Tomashevskii、V. V. Sokolov、A. A. Potekhin

  DOI：10.1023/a:1025592320130

  日期：——

  (alpha-Chloroalkyl)thiiranes react with sodium phenolates at heating in water-alcohol mixtures furnishing phenoxymethylthiiranes, 3-phenoxythietanes (resulting from thiirane-thietane rearrangement), or their mixture. The increased polarity of solvent favors the thiirane-thietane rearrangement. 2,2-Dimethyl-3-(chloromethyl)thiirane forms an exclusion for it does not afford (phenoxymethyl)thiirane even in anhydrous ethanol. Diastereomeric erythro- and threo-(1-chloroethyl)thiiranes react stereospecifically giving 2-methyl-3-phenoxymethylthiiranes or 2-methyl-3-phenoxythietanes of trans- and cis-configuration respectively. Specific features of these reactions are discussed from the viewpoint of solvent polarity effect on the competition between formal chlorine substitution along "recyclization" mechanism or through thiirane-thietane rearrangement.