methyl (2S,3aR,7aR)-1-benzyl-6-oxooctahydroindole-2-carboxylate ethylene acetal | 908290-16-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,3aR,7aR)-1-benzyl-6-oxooctahydroindole-2-carboxylate ethylene acetal
• 英文别名: methyl (2'S,3'aR,7'aR)-1'-benzylspiro[1,3-dioxolane-2,6'-3,3a,4,5,7,7a-hexahydro-2H-indole]-2'-carboxylate
• CAS: 908290-16-4
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: DPTSTIPVWWEPEM-IXDOHACOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S,3aR,7aR)-1-benzyl-6-oxooctahydroindole-2-carboxylate ethylene acetal 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 8.17h， 生成 (2S,3aR,7aR)-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：

  乙二醇 、 methyl (2S,3aR,7aR)-1-benzyl-6-oxo-octahydroindole-2-carboxylate 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 methyl (2S,3aR,7aR)-1-benzyl-6-oxooctahydroindole-2-carboxylate 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.