L-{2-[(2,6-difluoro-phenyl)-(2-methyl-6-nitro-benzoyl)-amino]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: L-{2-[(2,6-difluoro-phenyl)-(2-methyl-6-nitro-benzoyl)-amino]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-(2,6-difluoro-N-(2-methyl-6-nitrobenzoyl)anilino)-1-oxopropan-2-yl]carbamate
• 化学式: C₂₂H₂₃F₂N₃O₆
• 分子量: 463.438
• InChiKey: AQMCGFHNNYPQSD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  L-{2-[(2,6-difluoro-phenyl)-(2-methyl-6-nitro-benzoyl)-amino]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester 在 溶剂黄146 、 锌 作用下， 反应 2.0h， 以4.35 g的产率得到tert-butyl (S)-1-(3-(2,6-difluorophenyl)-5-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)ethylcarbamate
  参考文献：
  名称：

  A Novel Highly Stereoselective Synthesis of 2,3-Disubstituted 3H-Quinazoline-4-one Derivatives

  摘要：

  An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee > 93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.

  DOI：

  10.1021/ol070276c
• 作为产物：
  描述：

  2-甲基-6-硝基苯甲酰氯 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.42h， 生成 L-{2-[(2,6-difluoro-phenyl)-(2-methyl-6-nitro-benzoyl)-amino]-1-methyl-2-oxo-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  A Novel Highly Stereoselective Synthesis of 2,3-Disubstituted 3H-Quinazoline-4-one Derivatives

  摘要：

  An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee > 93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.

  DOI：

  10.1021/ol070276c

文献信息

• [EN] METHOD OF PREPARING 3-PHENYL-2-[9H-PURIN-6-YLAMINO)-METHYL]-3H-QUINAZOLIN-4-ONE AND SUBSTITUTED AND RELATED COMPOUNDS<br/>[FR] MÉTHODE DE PRÉPARATION DU 3-PHÉNYLE-2-[9H-PURINE-6-YLAMINO)-MÉTHYLE]-3H-QUINAZOLINE-4-UN ET COMPOSÉS SUBSTITUÉS ET ASSOCIÉS
  申请人：ICOS CORP

  公开号：WO2005113554A3

  公开（公告）日：2006-04-06
• A Novel Highly Stereoselective Synthesis of 2,3-Disubstituted <i>3H</i>-Quinazoline-4-one Derivatives
  作者：Paul Zhichkin、Edward Kesicki、Jennifer Treiberg、Lisa Bourdon、Matthew Ronsheim、Hua Chee Ooi、Stephen White、Angela Judkins、David Fairfax

  DOI：10.1021/ol070276c

  日期：2007.3.1

  An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee > 93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.