6,10b-dihydro-10b-methyl-5H-oxazolo[2,3-a]isoquinolin-2,3-dione | 135365-16-1

• 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: 6,10b-dihydro-10b-methyl-5H-oxazolo[2,3-a]isoquinolin-2,3-dione
• 英文别名: 10b-Methyl-5,6-dihydro-[1,3]oxazolo[2,3-a]isoquinoline-2,3-dione
• CAS: 135365-16-1
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: RVMRSFPRTWNPAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,10b-dihydro-10b-methyl-5H-oxazolo[2,3-a]isoquinolin-2,3-dione 在 硫酸 作用下， 以 甲醇 为溶剂， 生成 1-甲基-3,4-二氢异喹啉
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014
• 作为产物：
  描述：

  N-(2-苯乙基)乙酰胺 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 6,10b-dihydro-10b-methyl-5H-oxazolo[2,3-a]isoquinolin-2,3-dione
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014

文献信息

• NOVEL PYRIMIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：YUHAN CORPORATION, LTD.

  公开号：EP1131312A1

  公开（公告）日：2001-09-12
• US6545008B1
  申请人：——

  公开号：US6545008B1

  公开（公告）日：2003-04-08
• [EN] NOVEL PYRIMIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF<br/>[FR] NOUVEAUX DERIVES DE PYRIMIDINE ET LEURS PROCEDES DE PREPARATION
  申请人：YUHAN CORP

  公开号：WO2000029403A1

  公开（公告）日：2000-05-25

  The present invention relates to novel pyrimidine derivatives and pharmaceutically acceptable non-toxic salts thereof which possess an excellent inhibitory activity against gastric acid secretion, a pharmaceutical composition containing the same as an active ingredient, and a process for the preparation thereof.
• A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines
  作者：Robert D. Larsen、Robert A. Reamer、Edward G. Corley、Paul Davis、Edward J. J. Grabowski、Paul J. Reider、Ichiro Shinkai

  DOI：10.1021/jo00021a014

  日期：1991.10

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.