tert-butyl 5-cyano-6-(dimethylamino)-8-(naphthalen-2-yl)-2-oxo-3,4-dihydroquinazoline-1(2H)-carboxylate | 1134262-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: tert-butyl 5-cyano-6-(dimethylamino)-8-(naphthalen-2-yl)-2-oxo-3,4-dihydroquinazoline-1(2H)-carboxylate
• 英文别名: Tert-butyl 5-cyano-6-(dimethylamino)-8-naphthalen-2-yl-2-oxo-3,4-dihydroquinazoline-1-carboxylate；tert-butyl 5-cyano-6-(dimethylamino)-8-naphthalen-2-yl-2-oxo-3,4-dihydroquinazoline-1-carboxylate
• CAS: 1134262-67-1
• 化学式: C₂₆H₂₆N₄O₃
• 分子量: 442.517
• InChiKey: FZCITFCUSPAOMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  、 di-tert-butyl (2-oxopropane-1,3-diyl)dicarbamate 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以72%的产率得到tert-butyl 5-cyano-6-(dimethylamino)-8-(naphthalen-2-yl)-2-oxo-3,4-dihydroquinazoline-1(2H)-carboxylate
  参考文献：
  名称：

  Base dependent purported synthesis of congested 2-aminobenzylamines and tetrahydro-2-oxoquinazolines from 2-pyranones

  摘要：

  An expeditious and concise synthesis of highly congested 2-amino-3-aminomethyl-5-methylsulfanyl/-sec-aminobiphenyl-4-carbonitrile 4 and 1-tert-butoxycarbonyl-6-sec-amino-8-aryl-5-cyano-2-oxo-1,2,3, 4-tetrahydroquinazoline 5 has been delineated through base catalyzed ring transformation of 6-aryl-4-methylsulfanyl/-sec-amino-2H-pyran-2-one-3-carbonitrile 1 with 1,3-bis(tert-butoxycarbonylamino)-2-propanone 2, followed by TFA catalyzed hydrolysis of the intermediate [3-tert-butoxycarbonyl-aminomethyl-4-cyano-5-methylsulfanyl/-sec-aminobiphenyl-2-yl]carbamic acid tert-butyl ester 3 in moderate yield. The mechanism of formation of 5 has been established through isolation and transformation of the intermediate 3 to the 1-tert-butoxycarbonyl-6-sec-amino-8-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydroquinazoline. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.041

文献信息

• Base dependent purported synthesis of congested 2-aminobenzylamines and tetrahydro-2-oxoquinazolines from 2-pyranones
  作者：Farhanullah、Farhana Samrin、Vishnu Ji Ram

  DOI：10.1016/j.tet.2008.12.041

  日期：2009.2

  An expeditious and concise synthesis of highly congested 2-amino-3-aminomethyl-5-methylsulfanyl/-sec-aminobiphenyl-4-carbonitrile 4 and 1-tert-butoxycarbonyl-6-sec-amino-8-aryl-5-cyano-2-oxo-1,2,3, 4-tetrahydroquinazoline 5 has been delineated through base catalyzed ring transformation of 6-aryl-4-methylsulfanyl/-sec-amino-2H-pyran-2-one-3-carbonitrile 1 with 1,3-bis(tert-butoxycarbonylamino)-2-propanone 2, followed by TFA catalyzed hydrolysis of the intermediate [3-tert-butoxycarbonyl-aminomethyl-4-cyano-5-methylsulfanyl/-sec-aminobiphenyl-2-yl]carbamic acid tert-butyl ester 3 in moderate yield. The mechanism of formation of 5 has been established through isolation and transformation of the intermediate 3 to the 1-tert-butoxycarbonyl-6-sec-amino-8-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydroquinazoline. (C) 2009 Elsevier Ltd. All rights reserved.