methyl 4-(thietane-3-yloxy)benzoate | 647033-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(thietane-3-yloxy)benzoate
• 英文别名: Benzoic acid, 4-(3-thietanyloxy)-, methyl ester；methyl 4-(thietan-3-yloxy)benzoate
• CAS: 647033-03-2
• 化学式: C₁₁H₁₂O₃S
• 分子量: 224.28
• InChiKey: JJIRFPSSCUJUMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(thietane-3-yloxy)benzoate 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以93%的产率得到4-(thietane-3-yloxy)benzoic acid
  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
• 作为产物：
  描述：

  2-(氯甲基)环硫乙烷 、 sodium methylparaben 以 甲醇 、 水 为溶剂， 反应 2.0h， 以68%的产率得到methyl 4-(thietane-3-yloxy)benzoate
  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.