(5R,10aS)-5-tert-butyl-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-3-one

• 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: (5R,10aS)-5-tert-butyl-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-3-one
• 英文别名: (5R,10aS)-5-tert-butyl-1,5,10,10a-tetrahydro-[1,3]oxazolo[3,4-b]isoquinolin-3-one
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: UXKHLDKSIHKWIP-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R,10aS)-5-tert-butyl-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-3-one 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以89%的产率得到[(1R,3S)-1-tert-butyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol
  参考文献：
  名称：

  Efficient Direct and Modular Stereoselective Synthesis of Highly Functionalized Tetrahydroisoquinolines and C 2-1,1′-Bitetrahydroisoquinolines

  摘要：

  An efficient modular stereoselective synthesis of highly functionalized tetrahydroisoquinolines and C-2-1,1'-bitetrahydroisoquinolines chiral ligands is disclosed. The synthetic methodology relies on direct stereoselective Pictet-Spengler cyclization between (S)-4-benzyloxazolidin-2-ones and various mono-and dialdehydes using inexpensive sulfuric acid as the catalyst.

  DOI：

  10.1055/s-0034-1378892
• 作为产物：
  描述：

  (S)-4-苄基-2-唑烷酮 、 特戊醛 在 硫酸 作用下， 以 氯仿 为溶剂， 以83%的产率得到(5R,10aS)-5-tert-butyl-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-3-one
  参考文献：
  名称：

  Efficient Direct and Modular Stereoselective Synthesis of Highly Functionalized Tetrahydroisoquinolines and C 2-1,1′-Bitetrahydroisoquinolines

  摘要：

  An efficient modular stereoselective synthesis of highly functionalized tetrahydroisoquinolines and C-2-1,1'-bitetrahydroisoquinolines chiral ligands is disclosed. The synthetic methodology relies on direct stereoselective Pictet-Spengler cyclization between (S)-4-benzyloxazolidin-2-ones and various mono-and dialdehydes using inexpensive sulfuric acid as the catalyst.

  DOI：

  10.1055/s-0034-1378892

文献信息

• Efficient Direct and Modular Stereoselective Synthesis of Highly Functionalized Tetrahydroisoquinolines and C 2-1,1′-Bitetrahydroisoquinolines
  作者：Zaher Judeh、Khong Thinh

  DOI：10.1055/s-0034-1378892

  日期：——

  An efficient modular stereoselective synthesis of highly functionalized tetrahydroisoquinolines and C-2-1,1'-bitetrahydroisoquinolines chiral ligands is disclosed. The synthetic methodology relies on direct stereoselective Pictet-Spengler cyclization between (S)-4-benzyloxazolidin-2-ones and various mono-and dialdehydes using inexpensive sulfuric acid as the catalyst.