1,4-Dimethyl-4-phenyl-Δ⁴-imidazolin-thion-(2) | 23187-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,4-Dimethyl-4-phenyl-Δ⁴-imidazolin-thion-(2)
• 英文别名: 1,4-Dimethyl-5-phenyl-4-imidazolin-2-thion；1,4-dimethyl-5-phenyl-1,3-dihydro-imidazole-2-thione；3,5-dimethyl-4-phenyl-1H-imidazole-2-thione
• CAS: 23187-13-5
• 化学式: C₁₁H₁₂N₂S
• 分子量: 204.296
• InChiKey: JAMVOCSHBIFPKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4-Dimethyl-4-phenyl-Δ⁴-imidazolin-thion-(2) 、 1,1,3,3-四甲基-5-硫杂-7,8-二氮杂螺[3.4]辛-7-烯-2-酮 以 氯仿 为溶剂， 反应 5.0h， 以82%的产率得到3-<(1,4-dimethyl-5-phenylimidazol-2-yl)thio>-2,2,4,4-tetramethyl-3-(methylthio)cyclobutanone
  参考文献：
  名称：

  Trapping of a Thiocarbonyl Ylide with Imidazolethiones, Pyrimidinethione, and Thioamides

  摘要：

  The reactions of 1,1,3,3-tetramethyl-8-thia-5,6-diazaspirol[3.4]oct-5-en-2-one (1a) with imidazole-2-thiones 3 and pyrimidine-2(1H)-thione (6) in CHCl3 at 40-50 degrees yield 2,2,4,4-tetramethylcyclobutanone dithioacetals of type 4 and 7 respectively, by interception of the intermediate thiocarbonyl ylide 2a (Scheme 2).; product by 1,3-dipolar electrocyclization of 2a. When thioacetamide (8a) and Thiirane 5 is formed as a minor thiobenzamide (8b) are used as trapping reagents. the primary adduct 10 undergoes a spontaneous cyclization by intramolecular nucleophilic addition of the imino group at the carbonyl group to yield bicyclic products of type 9. The structure of 9a has been established by X-ray crystallography.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<290::aid-hlca290>3.0.co;2-p

文献信息

• Trapping of a Thiocarbonyl Ylide with Imidazolethiones, Pyrimidinethione, and Thioamides
  作者：Grzegorz Mlostoń、Tomasz Gendek、Anthony Linden、Heinz Heimgartner

  DOI：10.1002/(sici)1522-2675(19990210)82:2<290::aid-hlca290>3.0.co;2-p

  日期：1999.2.10

  The reactions of 1,1,3,3-tetramethyl-8-thia-5,6-diazaspirol[3.4]oct-5-en-2-one (1a) with imidazole-2-thiones 3 and pyrimidine-2(1H)-thione (6) in CHCl3 at 40-50 degrees yield 2,2,4,4-tetramethylcyclobutanone dithioacetals of type 4 and 7 respectively, by interception of the intermediate thiocarbonyl ylide 2a (Scheme 2).; product by 1,3-dipolar electrocyclization of 2a. When thioacetamide (8a) and Thiirane 5 is formed as a minor thiobenzamide (8b) are used as trapping reagents. the primary adduct 10 undergoes a spontaneous cyclization by intramolecular nucleophilic addition of the imino group at the carbonyl group to yield bicyclic products of type 9. The structure of 9a has been established by X-ray crystallography.