(E)-3-acetylsulfanyl-1-propen-1-ol | 1415555-61-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: (E)-3-acetylsulfanyl-1-propen-1-ol
• 英文别名: S-[(E)-3-hydroxyprop-2-enyl] ethanethioate
• CAS: 1415555-61-1
• 化学式: C₅H₈O₂S
• 分子量: 132.183
• InChiKey: CYLMSTFOMALZJB-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯醛 、 硫代乙酸 以 氘代丙酮 、 二氯甲烷 为溶剂， 反应 0.33h， 以69.3%的产率得到(Z)-3-acetylsulfanyl-1-propen-1-ol
  参考文献：
  名称：

  Reversible Generation of Metastable Enols in the 1,4-Addition of Thioacetic Acid to α,β-Unsaturated Carbonyl Compounds

  摘要：

  Addition of thioacetic acid to reactive alpha,beta-unsaturated carbonyl compounds like acrolein or crotonaldehyde in acetone-d(6) generates metastable (E)- and (Z)-1-alkenols, which tautomerize slowly at ambient temperature. The 1,4-addition of thioacetic acid and crotonaldehyde to (Z)-3-(acetylsulfanyl)-1-propen-1-ol is reversible with K-eq = 5.5 +/- 0.5 L/mol. A concerted, cyclic 1,4-addition mode is proposed to explain the preferred (Z)-stereoselectivity in lower polarity, nonprotic solvents.

  DOI：

  10.1021/jo3021709

文献信息

• Reversible Generation of Metastable Enols in the 1,4-Addition of Thioacetic Acid to α,β-Unsaturated Carbonyl Compounds
  作者：Lukas Hintermann、Aleksej Turočkin

  DOI：10.1021/jo3021709

  日期：2012.12.21

  Addition of thioacetic acid to reactive alpha,beta-unsaturated carbonyl compounds like acrolein or crotonaldehyde in acetone-d(6) generates metastable (E)- and (Z)-1-alkenols, which tautomerize slowly at ambient temperature. The 1,4-addition of thioacetic acid and crotonaldehyde to (Z)-3-(acetylsulfanyl)-1-propen-1-ol is reversible with K-eq = 5.5 +/- 0.5 L/mol. A concerted, cyclic 1,4-addition mode is proposed to explain the preferred (Z)-stereoselectivity in lower polarity, nonprotic solvents.