2-ethyl-1,3,4-thiazidin-5-one | 1187371-83-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻嗪类
• 英文名称: 2-ethyl-1,3,4-thiazidin-5-one
• CAS: 1187371-83-0
• 化学式: C₅H₁₀N₂OS
• 分子量: 146.213
• InChiKey: ZMHKTINXFQLCRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.13
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-硫基乙酰肼 、 丙醛 以 甲醇 为溶剂， 反应 2.0h， 以75%的产率得到2-ethyl-1,3,4-thiazidin-5-one
  参考文献：
  名称：

  Heterocycles from aroylacetic aldehydes and SH-containing hydrazides

  摘要：

  Condensation products of aroylacetic aldehydes with hydrazides of thioglycolic, 3-mercaptopropionic and 2-mercaptobenzoic acids exist in cyclic 1,3,4-thiadiazine, 1,3,4-thiadiazepine, or 1,3,4-benzothiadiazepine forms arising at the intramolecular addition of the mercapto group to the C=N bond of the initially formed hydrazone tautomer. The appearance of an alternative 5-hydroxy-2-pyrazoline form is favored by introduction of a strong electron-acceptor substituent into the aromatic ring of the 1,3-ketoaldehyde or by going over to benzoylacetone derivatives. In solutions the derivatives of aroylacetic aldehydes and of benzoylacetone show no tendency to tautomeric transition into linear hydrazine or enhydrazine forms.

  DOI：

  10.1134/s1070428009020225

文献信息

• Tautomerism and conformational isomerism of mercaptoacetylhydrazones of aliphatic and aromatic aldehydes
  作者：A. Yu. Ershov、I. V. Lagoda、S. I. Yakimovich、V. V. Pakal’nis、I. V. Zerova、A. V. Dobrodumov、V. V. Shamanin

  DOI：10.1134/s1070428009050030

  日期：2009.5

  Mercaptoacetylhydrazones of aliphatic and aromatic aldehydes exist in the solutions as tautomeric mixtures of open-chain and cyclic 1,3,4-thiadiazine forms. The linear hydrazone form consists of a set of isomers due to the configurational and conformational isomerism. At growing bulk of the alkyl substituent at the C=N bond of the aliphatic aldehydes derivatives decreases the fraction of the cyclic tautomer; therewith the logarithms of the constants of the chain-ring tautomeric equilibrium correlate with the steric constants of the alkyl substituents. In the series of the aromatic aldehydes mercaptoacetylhydrazones the linear tautomer prevails, and the equilibrium position is insignificantlyt affected at variation of the electronic characteristics of the substituents in the aromatic ring.