(5R,10aS)-5-phenyl-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-phenyl-1,5,10,10a-tetrahydro<1,3>oxazolo<3,4-b>isoquinolin-3-one
• 英文别名: (5R,10aS)-5-phenyl-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-3-one；(5R,10aS)-5-phenyl-1,5,10,10a-tetrahydro-[1,3]oxazolo[3,4-b]isoquinolin-3-one
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: HINFITMBBWDBOL-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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-phenyl-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93%的产率得到[(1R,3S)-1-penyl-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 、 苯甲醛 在 T406石油添加剂 、 四氯化钛 、 对甲苯磺酸 作用下， 生成 (5R,10aS)-5-phenyl-1,5,10,10a-tetrahydro<1,3>oxazolo<3,4-b>isoquinolin-3-one
  参考文献：
  名称：

  Stereospecific synthesis of oxazolo[3,4-b]tetrahydroisoquinolin-3-ones, analogs of podophyllotoxin, via benzotriazole methodology

  摘要：

  A stereospecific synthesis of 2-azapodophyllotoxin analogues based on benzotriazole methodology is reported. Intramolecular Friedel-Crafts reactions of benzotriazole Mannich adducts 2/3b-1 afforded 5-substituted oxazolo[3,4-b]tetrahydroisoquinolines 5b-1 as pure stereoisomers. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00506-0

文献信息

• Diastereoselective synthesis of oxazolo[3,4-b]tetrahydroisoquinolin-3-ones via Lewis acid TMSOTf-mediated Pictet–Spengler reaction
  作者：Zhenbei Zhang、Tong-Xin Liu、Qingfeng Liu、Zhiguo Zhang、Guisheng Zhang

  DOI：10.1016/j.tetasy.2013.10.015

  日期：2013.12

  An alternative and efficient method to stereoselectively synthesize oxazolo[3,4-b]tetrahydroisoquinolin-3-ones via a Pictet-Spengler reaction promoted by Lewis acid TMSOTf from readily available (S)-4-benzyl-2-oxazolidinone with various aromatic, aliphatic, and cyclic aldehydes under room temperature is described. (C) 2013 Elsevier Ltd. All rights reserved.