3-chloro-4-(2-hydroxyethylsulfanyl)-5-methoxyfuran-2(5H)-one | 1150099-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-chloro-4-(2-hydroxyethylsulfanyl)-5-methoxyfuran-2(5H)-one
• 英文别名: 3-Chloro-4-(2-hydroxyethylsulfanyl)-5-methoxy-furan-2(5h)-one；4-chloro-3-(2-hydroxyethylsulfanyl)-2-methoxy-2H-furan-5-one
• CAS: 1150099-98-1
• 化学式: C₇H₉ClO₄S
• 分子量: 224.665
• InChiKey: NEYQJTNKPOHSAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-dichloro-5-methoxy-2-(5H)furanone 、 2-巯基乙醇 在 三乙胺 作用下， 以 丙酮 为溶剂， 反应 60.0h， 以58%的产率得到3-chloro-4-(2-hydroxyethylsulfanyl)-5-methoxyfuran-2(5H)-one
  参考文献：
  名称：

  Reactions of 2-sulfanylethanol with mucochloric acid and its derivatives

  摘要：

  Mucochloric acid reacted with 2-sulfanylethanol in the presence of triethylamine to give 3-chloro-5-hydroxy-4-(2-hydroxyethylsulfanyl)furan-2(5H)-one which underwent acid-catalyzed cyclization to 7-chloro-2,3,4a,6-tetrahydrofuro[2,3-b][1,4]oxathiin-6-one. Likewise, reactions of 5H)-alkoxy-3,4-dichlorofuran-2(5H-ones with 2-sulfanylethanol in the presence of triethylamine involved replacement of chlorine in position 4 of the furan ring with formation of the corresponding 4-(2-hydroxyethylsulfanyl) derivatives. The reaction of mucochloric acid with 2-sulfanylethanol in excess aqueous potassium hydroxide resulted in the formation of an acyclic product, 3,(2-hydroxyethylsulfanyl)-2-chloroprop-2-enoic acid. The structure of 7-chloro-2,3,4a,6-tetrzhydrofluro[2,3-b][1,4]oxathiin-6-one and 3-(2-hydroxyethylsulfanyl)-2-chloroprop-2-enoic acid was proved by X-ray analysis.

  DOI：

  10.1134/s1070428008080204

文献信息

• Reactions of 2-sulfanylethanol with mucochloric acid and its derivatives
  作者：N. F. Devyatova、L. S. Kosolapova、A. R. Kurbangalieva、E. A. Berdnikov、O. A. Lodochnikova、I. A. Litvinov、G. A. Chmutova

  DOI：10.1134/s1070428008080204

  日期：2008.8

  Mucochloric acid reacted with 2-sulfanylethanol in the presence of triethylamine to give 3-chloro-5-hydroxy-4-(2-hydroxyethylsulfanyl)furan-2(5H)-one which underwent acid-catalyzed cyclization to 7-chloro-2,3,4a,6-tetrahydrofuro[2,3-b][1,4]oxathiin-6-one. Likewise, reactions of 5H)-alkoxy-3,4-dichlorofuran-2(5H-ones with 2-sulfanylethanol in the presence of triethylamine involved replacement of chlorine in position 4 of the furan ring with formation of the corresponding 4-(2-hydroxyethylsulfanyl) derivatives. The reaction of mucochloric acid with 2-sulfanylethanol in excess aqueous potassium hydroxide resulted in the formation of an acyclic product, 3,(2-hydroxyethylsulfanyl)-2-chloroprop-2-enoic acid. The structure of 7-chloro-2,3,4a,6-tetrzhydrofluro[2,3-b][1,4]oxathiin-6-one and 3-(2-hydroxyethylsulfanyl)-2-chloroprop-2-enoic acid was proved by X-ray analysis.