3-(hydroxymethyl)-2-thioxothiazolidin-4-one | 59320-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 3-(hydroxymethyl)-2-thioxothiazolidin-4-one
• 英文别名: 3-hydroxymethylrhodanine；3-Hydroxymethylrhodanine；3-(hydroxymethyl)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 59320-80-8
• 化学式: C₄H₅NO₂S₂
• 分子量: 163.221
• InChiKey: SXTWJIPLUYMRQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  罗丹宁 、 聚合甲醛 以 乙醇 、 水 为溶剂， 生成 3-(hydroxymethyl)-2-thioxothiazolidin-4-one 、 2-(hydroxymethylsulfanyl)-1,3-thiazol-4-one
  参考文献：
  名称：

  Hydroxymethylation of rhodanine

  摘要：

  Rhodanine in alcohol solution reacts with formaldehyde aqueous solution to form 3-hydroxymethylrhodanine. In the presence of triethylamine occurred also bis-hydroxymethylation at 5 position of the thiazolidine ring, but we failed to isolate the 3,5,5-trishydroxymethyl derivative in an individual form. The treatment of crude rhodanine 3,5,5-trishydroxymethyl derivative with benzaldehyde in boron trifluoride etherate leads to thioxo-8-phenyl-7,9-dioxa-1-thia-3-azaspiro[4.5]decan-4-one. The dissolution of the latter in aqueous alkali followed by neutralization with acid gives 5-sulfanyl-2-phenyl-1,3-dioxane-5-carboxylic acid.

  DOI：

  10.1134/s1070363210030230

文献信息

• Hydroxymethylation of rhodanine
  作者：Sun Min’yan’、S. M. Ramsh、S. Yu. Solov’eva、V. I. Zakharov

  DOI：10.1134/s1070363210030230

  日期：2010.3

  Rhodanine in alcohol solution reacts with formaldehyde aqueous solution to form 3-hydroxymethylrhodanine. In the presence of triethylamine occurred also bis-hydroxymethylation at 5 position of the thiazolidine ring, but we failed to isolate the 3,5,5-trishydroxymethyl derivative in an individual form. The treatment of crude rhodanine 3,5,5-trishydroxymethyl derivative with benzaldehyde in boron trifluoride etherate leads to thioxo-8-phenyl-7,9-dioxa-1-thia-3-azaspiro[4.5]decan-4-one. The dissolution of the latter in aqueous alkali followed by neutralization with acid gives 5-sulfanyl-2-phenyl-1,3-dioxane-5-carboxylic acid.