2-thioacetylmethylenethiazolidine | 162149-53-3

• 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: 2-thioacetylmethylenethiazolidine
• 英文别名: (1E)-1-(1,3-thiazolidin-2-ylidene)propane-2-thione
• CAS: 162149-53-3
• 化学式: C₆H₉NS₂
• 分子量: 159.276
• InChiKey: MUMCQQSDRHNXAU-GQCTYLIASA-N

物化性质

• 沸点：
  263.8±50.0 °C(predicted)
• 密度：
  1.295±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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：
  69.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-thioacetylmethylenethiazolidine 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-((E)-2-Methylsulfanyl-propenyl)-4,5-dihydro-thiazole
  参考文献：
  名称：

  Alkylation of Enaminothiones: What causes the observed stereoselectivity?

  摘要：

  Alkylation of the enaminothiones 1 and 5 in the presence of base leads to the products 2 and 6 with preponderant or exclusive Z- configuration about the C=C. Acid catalysed equilibration of 2 leads to a mixture in which the E- isomer predominates, whereas in the case of 6, the Z- form appears to be the thermodynamically favoured one.

  DOI：

  10.1016/0040-4039(95)01989-u
• 作为产物：
  描述：

  (E)-2-(2-oxopropylidene)thiazolidine 在 劳森试剂 作用下， 以 苯 为溶剂， 反应 4.0h， 以85%的产率得到2-thioacetylmethylenethiazolidine
  参考文献：
  名称：

  Conformational preferences of α-functionalised keten-S,N-acetals: Potential role of SO and SS interactions in solution

  摘要：

  PMR spectra of carbonyl compounds 2a-k reveal significant variations in the population off and Z Isomers on changing the solvent from CDCl3 to DMSO-d(6). In non-polar media, the intramolecular N-H....O hydrogen bonded form is exclusively observed. In DMSO-d(6), the alternative Z form is also populated. A similar conformational switch is also noted in the corresponding thiones. Different interpretations are critically analysed. The most consistent explanation is suggested to involvean interplay of N-H....X hydrogen bonding and S...X attractive interaction (X=0,S) in these systems. Ah initio calculations support this interpretation.

  DOI：

  10.1016/0040-4020(94)01023-s

文献信息

• Conformational preferences of α-functionalised keten-S,N-acetals: Potential role of SO and SS interactions in solution
  作者：Arun N. Dixit、K. Venodhar Reddy、Abdul Rakeeb A.S. Deshmukh、Srinivasachari Rajappa、Bishwajit Ganguly、Jayaraman Chandrasekhar

  DOI：10.1016/0040-4020(94)01023-s

  日期：1995.1

  PMR spectra of carbonyl compounds 2a-k reveal significant variations in the population off and Z Isomers on changing the solvent from CDCl3 to DMSO-d(6). In non-polar media, the intramolecular N-H....O hydrogen bonded form is exclusively observed. In DMSO-d(6), the alternative Z form is also populated. A similar conformational switch is also noted in the corresponding thiones. Different interpretations are critically analysed. The most consistent explanation is suggested to involvean interplay of N-H....X hydrogen bonding and S...X attractive interaction (X=0,S) in these systems. Ah initio calculations support this interpretation.
• Alkylation of Enaminothiones: What causes the observed stereoselectivity?
  作者：Laxmikant N. Patkar、Abdul Rakeeb A.S. Deshmukh、Srinivasachari Rajappa

  DOI：10.1016/0040-4039(95)01989-u

  日期：1995.12

  Alkylation of the enaminothiones 1 and 5 in the presence of base leads to the products 2 and 6 with preponderant or exclusive Z- configuration about the C=C. Acid catalysed equilibration of 2 leads to a mixture in which the E- isomer predominates, whereas in the case of 6, the Z- form appears to be the thermodynamically favoured one.