methyl 3,3-dimethyl-9-oxo-2,4-dioxabicyclo[3.3.1]nonane-7α-carboxylate | 1254050-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,3-dimethyl-9-oxo-2,4-dioxabicyclo[3.3.1]nonane-7α-carboxylate
• CAS: 1254050-15-1
• 化学式: C₁₁H₁₆O₅
• 分子量: 228.245
• InChiKey: CEDQIBAEMVUHIO-RNLVFQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 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：
  0.82
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3,3-dimethyl-9-oxo-2,4-dioxabicyclo[3.3.1]nonane-7α-carboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以77%的产率得到methyl 3,3-dimethyl-9-oxo-2,4-dioxabicyclo[3.3.1]nonane-7β-carboxylate
  参考文献：
  名称：

  Stereoselective α,α′-Annelation Reactions of 1,3-Dioxan-5-ones

  摘要：

  Pyrrolidine enamines derived from three 1,3-dioxan-5-ones undergo (alpha,alpha'-annelation reactions with methyl alpha-(bromomethyl)acrylate to produce bridged 2,4-dioxabicyclo[3.3.1]-nonane ring systems with complete stereocontrol. Stereochemical outcomes have been rationalized based on steric and stereoelectronic interactions in intermediate boat-like conformations of the 1,3-dioxane ring and subsequent kinetic protonation to set an axial ester group on the cyclohexanone ring. Base-mediated ester epimerization provides the stereochemical array found in the highly oxygenated cyclohexane ring of phyllaemblic acid and glochicoccins B and D.

  DOI：

  10.1021/jo101531b
• 作为产物：
  描述：

  1-(2,2-dimethyl-4H-1,3-dioxin-5-yl)pyrrolidine 、 2-(溴甲基)丙烯酸甲酯 在 三乙胺 、 水 作用下， 以 乙腈 为溶剂， 反应 21.0h， 以0.353 g的产率得到methyl 3,3-dimethyl-9-oxo-2,4-dioxabicyclo[3.3.1]nonane-7α-carboxylate
  参考文献：
  名称：

  Stereoselective α,α′-Annelation Reactions of 1,3-Dioxan-5-ones

  摘要：

  Pyrrolidine enamines derived from three 1,3-dioxan-5-ones undergo (alpha,alpha'-annelation reactions with methyl alpha-(bromomethyl)acrylate to produce bridged 2,4-dioxabicyclo[3.3.1]-nonane ring systems with complete stereocontrol. Stereochemical outcomes have been rationalized based on steric and stereoelectronic interactions in intermediate boat-like conformations of the 1,3-dioxane ring and subsequent kinetic protonation to set an axial ester group on the cyclohexanone ring. Base-mediated ester epimerization provides the stereochemical array found in the highly oxygenated cyclohexane ring of phyllaemblic acid and glochicoccins B and D.

  DOI：

  10.1021/jo101531b