1-(Furan-2-yl)-1,2,3,4-tetrahydroisoquinolin-6-ol | 1258843-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1-(Furan-2-yl)-1,2,3,4-tetrahydroisoquinolin-6-ol
• CAS: 1258843-36-5
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: WJVVKJOTJGLYCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  糠醛 、 间羟基苯乙胺 在 Ca(hfip)₂ 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到1-(Furan-2-yl)-1,2,3,4-tetrahydroisoquinolin-6-ol
  参考文献：
  名称：

  Calcium-Promoted Pictet-Spengler Reactions of Ketones and Aldehydes

  摘要：

  Calcium bis-1,1,1,3,3,3-hexafluoroisopropoxide is shown to be an effective catalyst for Pictet-Spengler reactions of 3-hydroxyphenethylamine and 3-hydroxy-4-methoxyphenethylamine with various aldehydes and ketones. Previous Lewis acid catalyzed Pictet-Spengler reactions of unactivated ketones typically require two separate reactions (imine formation, cyclization) to obtain the same results. The reactions described within directly provide 1,1'-disubstituted tetrahydroisoquinolines from the corresponding amine and ketone. These rare examples of Pictet-Spengler reactions of unactivated ketones demonstrate the unique nature of calcium as a Lewis acid catalyst.

  DOI：

  10.1021/jo1019283

文献信息

• Calcium-Promoted Pictet-Spengler Reactions of Ketones and Aldehydes
  作者：Matthew J. Vanden Eynden、Kamala Kunchithapatham、James P. Stambuli

  DOI：10.1021/jo1019283

  日期：2010.12.17

  Calcium bis-1,1,1,3,3,3-hexafluoroisopropoxide is shown to be an effective catalyst for Pictet-Spengler reactions of 3-hydroxyphenethylamine and 3-hydroxy-4-methoxyphenethylamine with various aldehydes and ketones. Previous Lewis acid catalyzed Pictet-Spengler reactions of unactivated ketones typically require two separate reactions (imine formation, cyclization) to obtain the same results. The reactions described within directly provide 1,1'-disubstituted tetrahydroisoquinolines from the corresponding amine and ketone. These rare examples of Pictet-Spengler reactions of unactivated ketones demonstrate the unique nature of calcium as a Lewis acid catalyst.