(R)-1,1,1-trichloro-4-((S)-6,8-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-2-ol | 1127645-05-9

• 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: (R)-1,1,1-trichloro-4-((S)-6,8-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-2-ol
• CAS: 1127645-05-9
• 化学式: C₁₅H₂₀Cl₃NO₃
• 分子量: 368.688
• InChiKey: MLAFYTUAICCFPE-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.72
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (R)-1,1,1-trichloro-4-((S)-6,8-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-2-ol 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到tert-butyl (S)-6,8-dimethoxy-1-((R)-4,4,4-trichloro-3-hydroxybutyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde

  摘要：

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.

  DOI：

  10.1021/ol802992m
• 作为产物：
  描述：

  、 3,5-二甲氧基苯乙胺 在 溶剂黄146 作用下， 反应 24.0h， 以42%的产率得到(R)-1,1,1-trichloro-4-((R)-6,8-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)butan-2-ol
  参考文献：
  名称：

  Enantioselective Synthesis of Schulzeines B and C via a β-Lactone-Derived Surrogate for Bishomoserine Aldehyde

  摘要：

  Enantioselective syntheses of the glucosidase inhibitors schulzeines B and C were achieved by employing a Pictet-Spengler reaction of a beta-lactone-derived masked bishomoserine aldehyde. Subsequent Corey-Link reaction unveiled an alpha-azido acid enabling cyclization to the delta-lactam fused tetrahydroisoquinoline. An efficient synthesis of the trisulfate-bearing side chain featured a Noyori hydrogenation and a Sharpless dihydroxylation. An unexpected reaction of a pendant amine during a Corey-Link process opens avenues for the synthesis of proline and related amino acid derivatives.

  DOI：

  10.1021/ol802992m