{(4S,5S)-5-Hydroxymethyl-2-[(R)-8-(4-methoxy-phenyl)-1,4-dithia-8-aza-spiro[4.5]dec-7-yl]-2-methyl-[1,3]dioxolan-4-yl}-methanol | 259249-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: {(4S,5S)-5-Hydroxymethyl-2-[(R)-8-(4-methoxy-phenyl)-1,4-dithia-8-aza-spiro[4.5]dec-7-yl]-2-methyl-[1,3]dioxolan-4-yl}-methanol
• CAS: 259249-38-2
• 化学式: C₂₀H₂₉NO₅S₂
• 分子量: 427.586
• InChiKey: DWWYLQIPRQISTE-OKZBNKHCSA-N

物化性质

• 沸点：
  631.5±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  71.39
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  {(4S,5S)-5-Hydroxymethyl-2-[(R)-8-(4-methoxy-phenyl)-1,4-dithia-8-aza-spiro[4.5]dec-7-yl]-2-methyl-[1,3]dioxolan-4-yl}-methanol 在 四溴化碳 、 Raney Ni W₄ 、 三氟化硼乙醚 、 双(三甲基硅烷基)氨基钾 、 铜 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 1-(4-methoxyphenyl)-2-propylpiperidine
  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：

  (R)-7-[(4S,5S)-4,5-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-[1,3]dioxolan-2-yl]-8-(4-methoxy-phenyl)-1,4-dithia-8-aza-spiro[4.5]decane 在 n-Bu₄NH 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到{(4S,5S)-5-Hydroxymethyl-2-[(R)-8-(4-methoxy-phenyl)-1,4-dithia-8-aza-spiro[4.5]dec-7-yl]-2-methyl-[1,3]dioxolan-4-yl}-methanol
  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