4-(thietan-3-yloxy)benzaldehyde | 647033-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(thietan-3-yloxy)benzaldehyde
• CAS: 647033-02-1
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: PCMONHNUJSIDBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(氯甲基)环硫乙烷 、 4-羟基苯甲醛钠盐 以 甲醇 、 水 为溶剂， 反应 2.0h， 以69%的产率得到4-(thietan-3-yloxy)benzaldehyde
  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.