(1S,2S)-4,5-Dimethyl-2-p-tolyl-3,6-dihydro-2H-thiopyran 1-oxide | 106726-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: (1S,2S)-4,5-Dimethyl-2-p-tolyl-3,6-dihydro-2H-thiopyran 1-oxide
• CAS: 106726-56-1；106726-57-2
• 化学式: C₁₄H₁₈OS
• 分子量: 234.362
• InChiKey: BNRUYWAHKLPGKO-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (E)-(4-methylphenyl)methanethial S-oxide 、 2,3-二甲基-1,3-丁二烯 反应 100.0h， 生成 (1R,2S)-4,5-dimethyl-2-(4-methylphenyl)-3,6-dihydro-2H-thiopyran 1-oxide 、 (1S,2S)-4,5-Dimethyl-2-p-tolyl-3,6-dihydro-2H-thiopyran 1-oxide
  参考文献：
  名称：

  Thermal and Lewis acid induced cycloaddition of thioaldehyde S-oxides (monosubstituted sulfines) to dienes. 3

  摘要：

  The stereochemical course of the 1,4-cycloaddition of thioaldehyde S-oxides (monosubstituted sulfines) to 2,3-dimethylbuta-1,3-diene, buta-1,3-diene, and cis- and trans-penta-1,3-diene was investigated. Unexpectedly, the reactions of buta-1,3-diene and 2,3-dimethylbuta-1,3-diene with Z-monoaryl sulfines afforded cis/trans mixtures of the corresponding dihydrothiopyran S-oxides, in which the relative amounts of the two isomers depended upon the initial diene/sulfine ratio. A Z to E isomerization of the dienophiles during the cycloaddition was responsible. On the other hand, Z/E mixtures of aliphatic tert-butyl sulfine gave, with 2,3-dimethylbuta-1,3-diene, only the corresponding trans cycloadduct. Catalysis of the reaction by Lewis acids, heretofore largely unexplored, was also investigated.

  DOI：

  10.1021/jo00007a045