(2S,3R,4aS,8aS)-1-benzyl-3-hydroxy-2-methyl-7-oxodecahydroquinoline ethylene acetal | 908290-43-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,3R,4aS,8aS)-1-benzyl-3-hydroxy-2-methyl-7-oxodecahydroquinoline ethylene acetal
• 英文别名: (2'S,3'R,4'aS,8'aS)-1'-benzyl-2'-methylspiro[1,3-dioxolane-2,7'-2,3,4,4a,5,6,8,8a-octahydroquinoline]-3'-ol
• CAS: 908290-43-7
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: PCCBMPCOQSSQSS-LEUOFYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,4aS,8aS)-1-benzyl-3-hydroxy-2-methyl-7-oxodecahydroquinoline ethylene acetal 在 三氟乙酸酐 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal
  参考文献：
  名称：

  Ring Expansion of Functionalized Octahydroindoles to Enantiopure cis-Decahydroquinolines

  摘要：

  A new synthetic entry to enantiopure cis-decahydroquinolines is reported. Endo and exo derivatives of cis-1-benzyl-2-(hydroxymethyl) octahydroindol-6-one ethylene acetal undergo ring enlargement upon treatment with TFAA and then Et3N (thermodynamic conditions) to give enantiopure 1-benzyl-3-hydroxydecahydroquinolin-7-one derivatives in 77 and 82% yield, respectively. For 2-(1-hydroxyethyl) analogues, the best synthetic result is obtained from the (2S, 1'R) endo isomer, which under kinetic reaction conditions (MsCl, THF, -20 degrees C, then AgOAc at rt) gives the expanded product in 54% yield.

  DOI：

  10.1021/jo060592p
• 作为产物：
  描述：

  (2S,3aS,7aS)-1-benzyl-2-[(1'R)-1-hydroxyethyl]octahydroindol-6-one ethylene acetal 在 甲基磺酰氯 、 三乙胺 、 silver trifluoroacetate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以58%的产率得到(2S,3R,4aS,8aS)-1-benzyl-3-hydroxy-2-methyl-7-oxodecahydroquinoline ethylene acetal
  参考文献：
  名称：

  Ring Expansion of Functionalized Octahydroindoles to Enantiopure cis-Decahydroquinolines

  摘要：

  A new synthetic entry to enantiopure cis-decahydroquinolines is reported. Endo and exo derivatives of cis-1-benzyl-2-(hydroxymethyl) octahydroindol-6-one ethylene acetal undergo ring enlargement upon treatment with TFAA and then Et3N (thermodynamic conditions) to give enantiopure 1-benzyl-3-hydroxydecahydroquinolin-7-one derivatives in 77 and 82% yield, respectively. For 2-(1-hydroxyethyl) analogues, the best synthetic result is obtained from the (2S, 1'R) endo isomer, which under kinetic reaction conditions (MsCl, THF, -20 degrees C, then AgOAc at rt) gives the expanded product in 54% yield.

  DOI：

  10.1021/jo060592p

文献信息

• Ring Expansion of Functionalized Octahydroindoles to Enantiopure <i>cis</i>-Decahydroquinolines
  作者：Marisa Mena、Josep Bonjoch、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1021/jo060592p

  日期：2006.8.1

  A new synthetic entry to enantiopure cis-decahydroquinolines is reported. Endo and exo derivatives of cis-1-benzyl-2-(hydroxymethyl) octahydroindol-6-one ethylene acetal undergo ring enlargement upon treatment with TFAA and then Et3N (thermodynamic conditions) to give enantiopure 1-benzyl-3-hydroxydecahydroquinolin-7-one derivatives in 77 and 82% yield, respectively. For 2-(1-hydroxyethyl) analogues, the best synthetic result is obtained from the (2S, 1'R) endo isomer, which under kinetic reaction conditions (MsCl, THF, -20 degrees C, then AgOAc at rt) gives the expanded product in 54% yield.