(R)-2-((4S,5S)-4,5-Bis-hydroxymethyl-2-methyl-[1,3]dioxolan-2-yl)-1-(4-methoxy-phenyl)-2,3-dihydro-1H-pyridin-4-one | 259249-40-6

• 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: (R)-2-((4S,5S)-4,5-Bis-hydroxymethyl-2-methyl-[1,3]dioxolan-2-yl)-1-(4-methoxy-phenyl)-2,3-dihydro-1H-pyridin-4-one
• CAS: 259249-40-6
• 化学式: C₁₈H₂₃NO₆
• 分子量: 349.384
• InChiKey: MUPQWXQFQSIHTQ-YESZJQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.46
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  叔丁基二苯基氯硅烷 、 (R)-2-((4S,5S)-4,5-Bis-hydroxymethyl-2-methyl-[1,3]dioxolan-2-yl)-1-(4-methoxy-phenyl)-2,3-dihydro-1H-pyridin-4-one 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到(R)-2-[(4S,5S)-4,5-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-[1,3]dioxolan-2-yl]-1-(4-methoxy-phenyl)-2,3-dihydro-1H-pyridin-4-one
  参考文献：
  名称：

  Stereospecific Synthesis of Piperidine Skeleton by [4+2] Cycloaddition, Leading to the Synthesis of Piperidines of Biological Interests

  摘要：

  [4+2] Cycloaddition reaction between a chiral imine possessing an auxiliary derived from tartaric acid and Danishefsky diene was studied, and the reaction promoted by boron trifluoride etherate gave 2,3-dehydropiperidin-4-one in a stereospecific manner. The adduct thus obtained was converted into (S)-coniine derivatives without loss of the stereochemical integrity.

  DOI：

  10.3987/com-99-s47
• 作为产物：
  描述：

  (4S,5S)-4,5-Dimethoxymethyl-2-(N-p-methoxyphenyl)iminomethyl-2-methyl-1,3-dioxolane 在 二氯乙基铝 、 三溴化硼 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 0.67h， 生成 (R)-2-((4S,5S)-4,5-Bis-hydroxymethyl-2-methyl-[1,3]dioxolan-2-yl)-1-(4-methoxy-phenyl)-2,3-dihydro-1H-pyridin-4-one
  参考文献：
  名称：

  Stereospecific Synthesis of Piperidine Skeleton by [4+2] Cycloaddition, Leading to the Synthesis of Piperidines of Biological Interests

  摘要：

  [4+2] Cycloaddition reaction between a chiral imine possessing an auxiliary derived from tartaric acid and Danishefsky diene was studied, and the reaction promoted by boron trifluoride etherate gave 2,3-dehydropiperidin-4-one in a stereospecific manner. The adduct thus obtained was converted into (S)-coniine derivatives without loss of the stereochemical integrity.

  DOI：

  10.3987/com-99-s47