6,6-dimethyl-3-(1-o-toluidinoethylidene)tetrahydrothiopyran-2,4-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6,6-dimethyl-3-(1-o-toluidinoethylidene)tetrahydrothiopyran-2,4-dione
• 英文别名: (3E)-6,6-dimethyl-3-[1-(2-methylanilino)ethylidene]thiane-2,4-dione
• 化学式: C₁₆H₁₉NO₂S
• 分子量: 289.398
• InChiKey: SPSJDGSHNQTQPC-SDNWHVSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6,6-dimethyltetrahydrothiopyran-2,4-dione 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲苯 、 苯 为溶剂， 反应 9.5h， 生成 6,6-dimethyl-3-(1-o-toluidinoethylidene)tetrahydrothiopyran-2,4-dione
  参考文献：
  名称：

  摘要：

  The reaction of 3-acetyl-6,6-dimethyltetrahydrothiopyran-2,4-dione with diazomethane furnishes a mixture of 3-acetyl-6,6-dimethyl-4-methoxy-5,6-dihydro-2H-thiopyran-2-one and 3-acetyl-6,6-dimethyl-2-methoxy-5,6-dihydro-2H-thiopyran-4-one in 2: 3 ratio, whereas in reaction with dimethyl sulfate in the presence of potassium carbonate forms a mixture of the same products in 9: 1 ratio. In both reactions the overall yield of ethers amounts to 50%. Treating of regioisomeric enol methyl ethers with pyrrolidine, o-toluidine, and allylamine provides the corresponding endocyclic enaminodiketones.

  DOI：

  10.1023/a:1025544404200

文献信息

• ——
  作者：T. A. Zheldakova、M. V. Budnikova、D. B. Rubinov

  DOI：10.1023/a:1025544404200

  日期：——

  The reaction of 3-acetyl-6,6-dimethyltetrahydrothiopyran-2,4-dione with diazomethane furnishes a mixture of 3-acetyl-6,6-dimethyl-4-methoxy-5,6-dihydro-2H-thiopyran-2-one and 3-acetyl-6,6-dimethyl-2-methoxy-5,6-dihydro-2H-thiopyran-4-one in 2: 3 ratio, whereas in reaction with dimethyl sulfate in the presence of potassium carbonate forms a mixture of the same products in 9: 1 ratio. In both reactions the overall yield of ethers amounts to 50%. Treating of regioisomeric enol methyl ethers with pyrrolidine, o-toluidine, and allylamine provides the corresponding endocyclic enaminodiketones.