(5R,10aS)-5-propyl-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-propyl-1,5,10,10a-tetrahydro<1,3>oxazolo<3,4-b>isoquinolin-3-one
• 英文别名: (5R,10aS)-5-propyl-1,5,10,10a-tetrahydro[1,3]oxazolo[3,4-b]isoquinolin-3-one；(5R,10aS)-5-propyl-1,5,10,10a-tetrahydro-[1,3]oxazolo[3,4-b]isoquinolin-3-one
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: DXPCTMYRHYOCQL-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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-propyl-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85%的产率得到(1R,3S)-1-propyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline
  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：

  (4S,1'R)-3-[1-(phenylsulfonyl)butyl]-4-benzyloxazolidin-2-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.83h， 以98%的产率得到(5R,10aS)-5-propyl-1,5,10,10a-tetrahydro<1,3>oxazolo<3,4-b>isoquinolin-3-one
  参考文献：
  名称：

  Reactivity of chiral exocyclic N-acyliminium ions with aromatic derivatives

  摘要：

  Chiral N-acyliminium ions obtained from optically active N-[1-(phenylsulfonyl)alkyl]oxazolidin-2-ones at low temperature in the presence of titanium tetrachloride react with electron-rich aromatic compounds to afford the corresponding adducts in good yields and variable diastereoselectivities. Chemoselective cleavage of the oxazolidin-2-one ring with lithium/ammonia affords the corresponding benzylamines in enantioenriched form. The utilization of 4-benzyloxazolidin-2-one as a chiral auxiliary leads to intramolecular cyclization with exclusive formation of one diastereomer. The obtained tricyclic derivatives possess the core structure of some aza analogs of the anticancer drug podophyllotoxin. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00123-x

文献信息

• Stereospecific synthesis of oxazolo[3,4-b]tetrahydroisoquinolin-3-ones, analogs of podophyllotoxin, via benzotriazole methodology
  作者：Alan R. Katritzky、Justo Cobo-Domingo、Baozhen Yang、Peter J. Steel

  DOI：10.1016/s0957-4166(98)00506-0

  日期：1999.1

  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.