2,6,6-trimethyl-6h-pyran-3-carbothioic acid S-ethyl ester | 188676-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,6,6-trimethyl-6h-pyran-3-carbothioic acid S-ethyl ester
• 英文别名: S-ethyl 2,6,6-trimethylpyran-3-carbothioate
• CAS: 188676-63-3
• 化学式: C₁₁H₁₆O₂S
• 分子量: 212.313
• InChiKey: UCSFRBLZUALZRS-UHFFFAOYSA-N

物化性质

• 沸点：
  302.0±32.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6,6-trimethyl-6h-pyran-3-carbothioic acid S-ethyl ester 、 Arsonium, (4-methoxy-2,4-dioxobutyl)triphenyl-, bromide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以48%的产率得到(1R,5R,6R)-5-Ethylsulfanylcarbonyl-4-methyl-6-(2-methyl-propenyl)-2-oxo-cyclohex-3-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Novel Michael-Wittig reactions of methyl 3-oxo-4-(triphenylarsoranylidene)butanoate and substituted 2H-pyran-5-carboxylates; The synthesis of highly functionalised 2-cyclohexenonedicarboxylates

  摘要：

  Novel Michael-Wittig condensations of methyl 3-oxo-4-(triphenylarsoranylidene)-butanoate 6 and substituted 2,2-dimethyl-2H-pyran-5-carboxylates 5a to 5e gave substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8a to 8e in a mixture of three keto diastereomers and two enol diastereomers. Apart from substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8f to 8g, less hindered substituted 2-methyl-2H-pyran-5-carboxylates 5f and 5g gave the substituted tetrahydrobenzofurans 9f and 9g. 4-Halomethyl-6-oxo-4-cyclohexene 1,1-dicarboxylates 8 were mostly in the enol diastereomeric form. A plausible mechanism is given for the unique formation for these products. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01126-x
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 S-ethyl acetothioacetate 在 sodium benzoate 、 苄基三乙基氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 2,6,6-trimethyl-6h-pyran-3-carbothioic acid S-ethyl ester 、 S-ethyl (2Z)-2-acetyl-5-methylhexa-2,4-dienethioate
  参考文献：
  名称：

  Synthesis of Substituted Alkyl 2H-Pyran-5-carboxylates

  摘要：

  成功合成了取代烷基2H-吡喃-5-羧酸酯3，这一过程是通过取代烷基3-氧代丁酸酯1和共轭醛2反应得到的。

  DOI：

  10.1055/s-1997-1400

文献信息

• Moorhoff, Cornelis M., Journal of Chemical Research, Miniprint, 1997, # 4, p. 866 - 879
  作者：Moorhoff, Cornelis M.

  DOI：——

  日期：——
• Synthesis of Substituted Alkyl 2H-Pyran-5-carboxylates
  作者：Cornelis M. Moorhoff

  DOI：10.1055/s-1997-1400

  日期：1997.6

  The successful synthesis of substituted alkyl 2H-pyran-5-carboxylates 3 from substituted alkyl 3-oxobutanoates 1 and conjugated aldehydes 2 is described.

  成功合成了取代烷基2H-吡喃-5-羧酸酯3，这一过程是通过取代烷基3-氧代丁酸酯1和共轭醛2反应得到的。
• Novel Michael-Wittig reactions of methyl 3-oxo-4-(triphenylarsoranylidene)butanoate and substituted 2H-pyran-5-carboxylates; The synthesis of highly functionalised 2-cyclohexenonedicarboxylates
  作者：Cornelis M. Moorhoff

  DOI：10.1016/s0040-4020(96)01126-x

  日期：1997.2

  Novel Michael-Wittig condensations of methyl 3-oxo-4-(triphenylarsoranylidene)-butanoate 6 and substituted 2,2-dimethyl-2H-pyran-5-carboxylates 5a to 5e gave substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8a to 8e in a mixture of three keto diastereomers and two enol diastereomers. Apart from substituted 4-alkyl-6-oxo-4-cyclohexene-1,3-dicarboxylates 8f to 8g, less hindered substituted 2-methyl-2H-pyran-5-carboxylates 5f and 5g gave the substituted tetrahydrobenzofurans 9f and 9g. 4-Halomethyl-6-oxo-4-cyclohexene 1,1-dicarboxylates 8 were mostly in the enol diastereomeric form. A plausible mechanism is given for the unique formation for these products. (C) 1997, Elsevier Science Ltd.