methyl 4-<<(tert-butyldimethylsilyl)oxy>methyl>dithiobenzoate | 148064-90-8

• 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: methyl 4-<<(tert-butyldimethylsilyl)oxy>methyl>dithiobenzoate
• 英文别名: Methyl 4-[[tert-butyl(dimethyl)silyl]oxymethyl]benzenecarbodithioate
• CAS: 148064-90-8
• 化学式: C₁₅H₂₄OS₂Si
• 分子量: 312.572
• InChiKey: AGXFDBOAUSEUPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-phenyl-4-(methylthio)but-3-en-2-one 、 methyl 4-<<(tert-butyldimethylsilyl)oxy>methyl>dithiobenzoate 在 t-BOK 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到2-phenyl-6-<<<(4-tert-butyldimethylsilyl)oxy>methyl>phenyl>-4-H-thiopyran-4-one
  参考文献：
  名称：

  Synthesis of 2,6-diaryl-4H-thiopyran-4-ones

  摘要：

  A novel synthesis of 2,6-diaryl-4H-thiopyran-4-ones has been developed. The title compounds were prepared by two sequential thio-Claisen condensations of a dialkyl ketone and two dithioesters. The intermediate beta-thioxo ketone from the first condensation was converted to the corresponding beta-(methylthio) enone for both protection and reactivity purposes. Facile addition-elimination of the methylthio moiety by a beta-thioxo ketone enolate generated in the second thio-Claisen condensation afforded the desired heterocycle. This new method is rapid and simple with the only requirement being moderate substituent alkaline stability.

  DOI：

  10.1021/jo00063a023
• 作为产物：
  描述：

  4-溴苄醇 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 4-<<(tert-butyldimethylsilyl)oxy>methyl>dithiobenzoate
  参考文献：
  名称：

  Synthesis of 2,6-diaryl-4H-thiopyran-4-ones

  摘要：

  A novel synthesis of 2,6-diaryl-4H-thiopyran-4-ones has been developed. The title compounds were prepared by two sequential thio-Claisen condensations of a dialkyl ketone and two dithioesters. The intermediate beta-thioxo ketone from the first condensation was converted to the corresponding beta-(methylthio) enone for both protection and reactivity purposes. Facile addition-elimination of the methylthio moiety by a beta-thioxo ketone enolate generated in the second thio-Claisen condensation afforded the desired heterocycle. This new method is rapid and simple with the only requirement being moderate substituent alkaline stability.

  DOI：

  10.1021/jo00063a023

文献信息

• Boaz Neil W., Fox Kristine M., J. Org. Chem., 58 (1993) N 11, S 3042-3045
  作者：Boaz Neil W., Fox Kristine M.

  DOI：——

  日期：——
• Synthesis of 2,6-diaryl-4H-thiopyran-4-ones
  作者：Neil W. Boaz、Kristine M. Fox

  DOI：10.1021/jo00063a023

  日期：1993.5

  A novel synthesis of 2,6-diaryl-4H-thiopyran-4-ones has been developed. The title compounds were prepared by two sequential thio-Claisen condensations of a dialkyl ketone and two dithioesters. The intermediate beta-thioxo ketone from the first condensation was converted to the corresponding beta-(methylthio) enone for both protection and reactivity purposes. Facile addition-elimination of the methylthio moiety by a beta-thioxo ketone enolate generated in the second thio-Claisen condensation afforded the desired heterocycle. This new method is rapid and simple with the only requirement being moderate substituent alkaline stability.