1-benzyl-4-hydroxy-2-phenyl-2,3-dihydroindole | 1620143-05-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-benzyl-4-hydroxy-2-phenyl-2,3-dihydroindole
• 英文别名: 1-Benzyl-2-phenyl-2,3-dihydroindol-4-ol
• CAS: 1620143-05-6
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: VPDMCDVDGXICPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-4-hydroxy-2-phenyl-2,3-dihydroindole 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以93%的产率得到1-benzyl-4-tert-butyldimethylsilyloxy-2-phenylindole
  参考文献：
  名称：

  Ring-Opening Cyclization of Cyclohexane-1,3-dione-2-spirocyclopropanes with Amines: Rapid Access to 2-Substituted 4-Hydroxyindole

  摘要：

  An efficient ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes with primary amines has been developed. The reaction proceeded at room temperature without any additives to provide 2-substituted tetrahydroindol-4-ones in good to excellent yields without the formation of the 3-substituted isomers. The obtained product was readily converted into a 2-substituted 4-hydroxyindole derivative via a synthetically useful indoline intermediate.

  DOI：

  10.1021/ol501837b
• 作为产物：
  描述：

  1-phenylspiro[2.5]octane-4,8-dione 在 copper(ll) bromide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 5.5h， 生成 1-benzyl-4-hydroxy-2-phenyl-2,3-dihydroindole
  参考文献：
  名称：

  Ring-Opening Cyclization of Cyclohexane-1,3-dione-2-spirocyclopropanes with Amines: Rapid Access to 2-Substituted 4-Hydroxyindole

  摘要：

  An efficient ring-opening cyclization of cyclohexane-1,3-dione-2-spirocyclopropanes with primary amines has been developed. The reaction proceeded at room temperature without any additives to provide 2-substituted tetrahydroindol-4-ones in good to excellent yields without the formation of the 3-substituted isomers. The obtained product was readily converted into a 2-substituted 4-hydroxyindole derivative via a synthetically useful indoline intermediate.

  DOI：

  10.1021/ol501837b