2-methyl-2,2'-bi(1,3-oxathiolane)

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 2-methyl-2,2'-bi(1,3-oxathiolane)
• 英文别名: 2,2'-Bi-1,3-oxathiolane, 2-methyl-；2-methyl-2-(1,3-oxathiolan-2-yl)-1,3-oxathiolane
• 化学式: C₇H₁₂O₂S₂
• 分子量: 192.303
• InChiKey: MNSOXUUZUDONGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙氧基丙-2-烯醛 、 2-巯基乙醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以100%的产率得到2-methyl-2,2'-bi(1,3-oxathiolane)
  参考文献：
  名称：

  摘要：

  The reaction between 2-alkoxypropenals and 2-mercaptoethanol was studied at 20 and 60degreesC by means of H-1 NMR and GC-MS methods. Under kinetically controlled conditions (20degreesC, 7-30 days) with no catalyst the addition of 2-mercaptoethanol to 2-alkoxypropenals occurs along Markownikoff rule. The arising 2'-hydroxyethylthio-2-alkoxypropanal undergoes isomerization into the 2-hydroxy-3-alkoxy-3-methyl-1,4-oxathiane that at heating in the presence of catalytic amounts of acids is converted into 2-methyl-2-formyl-1, 3-oxathiolane. The reaction of 2-alkoxypropenals with 2-mercaptoethanol at heating (60degreesC, 3 h) in the presence of acids affords 2-methyl-2,2'-bi(1,3-oxathiolane) even at 2-mercaptoethanol deficit. At the double excess of the latter the 2-methyl-2,2'-bi(1,3-oxathiolane) was obtained in quantitative yield. The presumable schemes of conversion of 2-hydroxy-3-alkoxy-3-methyl-1,4-oxathiane into 2-methyl-2-formyl-1,3-oxathiolane and 2-acetyl-1,3-oxathiolane are discussed.

  DOI：

  10.1023/a:1013909715161

文献信息

• ——
  作者：N. A. Keiko、E. A. Funtikova、L. G. Stepanova、Yu. A. Chuvashev、A. I. Albanov、M. G. Voronkov

  DOI：10.1023/a:1013909715161

  日期：——

  The reaction between 2-alkoxypropenals and 2-mercaptoethanol was studied at 20 and 60degreesC by means of H-1 NMR and GC-MS methods. Under kinetically controlled conditions (20degreesC, 7-30 days) with no catalyst the addition of 2-mercaptoethanol to 2-alkoxypropenals occurs along Markownikoff rule. The arising 2'-hydroxyethylthio-2-alkoxypropanal undergoes isomerization into the 2-hydroxy-3-alkoxy-3-methyl-1,4-oxathiane that at heating in the presence of catalytic amounts of acids is converted into 2-methyl-2-formyl-1, 3-oxathiolane. The reaction of 2-alkoxypropenals with 2-mercaptoethanol at heating (60degreesC, 3 h) in the presence of acids affords 2-methyl-2,2'-bi(1,3-oxathiolane) even at 2-mercaptoethanol deficit. At the double excess of the latter the 2-methyl-2,2'-bi(1,3-oxathiolane) was obtained in quantitative yield. The presumable schemes of conversion of 2-hydroxy-3-alkoxy-3-methyl-1,4-oxathiane into 2-methyl-2-formyl-1,3-oxathiolane and 2-acetyl-1,3-oxathiolane are discussed.