(S)-(4-oxo-3,4-dihydroquinazolin-2-yl)(phenyl)methyl acetate | 1251849-62-3

• 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: (S)-(4-oxo-3,4-dihydroquinazolin-2-yl)(phenyl)methyl acetate
• 英文别名: 2-(α-Acetoxybenzyl)-4(3H)-quinazolinone
• CAS: 1251849-62-3
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: DWZUBTIXKLTHLE-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-(4-oxo-3,4-dihydroquinazolin-2-yl)(phenyl)methyl acetate 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 苯 为溶剂， 以99%的产率得到(S)-(4-chloroquinazolin-2-yl)(phenyl)methyl acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of (S)-4-aminoquinazoline alcohols

  摘要：

  A simple synthetic method for the preparation of enantiomerically pure (S)-4-aminoquinazoline alcohols from (S)-quinazolinone alcohols by key steps including chlorination, nucleophilic ipso substitution, and deacetylation is presented. Mutagenic and antimutagenic properties of the (S)-4-aminoquinazoline alcohols were investigated by using Salmonella typhimurium TA1535, and Escherichia colt WP2uvrA tester strains at 0.01, 0.1, and 1 mu g/plate concentrations. (S)-4-aminoquinazoline alcohols were found to be genotoxically safe at the tested concentrations. Among the tested (S)-4-aminoquinazoline alcohols, the best antimutagenic activity was obtained with a methyl derivative at 0.1 mu g/plate dose. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.040
• 作为产物：
  描述：

  (S)-2-[hydroxy(phenyl)methyl]quinazolin-4(3H)-one 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到(S)-(4-oxo-3,4-dihydroquinazolin-2-yl)(phenyl)methyl acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of (S)-4-aminoquinazoline alcohols

  摘要：

  A simple synthetic method for the preparation of enantiomerically pure (S)-4-aminoquinazoline alcohols from (S)-quinazolinone alcohols by key steps including chlorination, nucleophilic ipso substitution, and deacetylation is presented. Mutagenic and antimutagenic properties of the (S)-4-aminoquinazoline alcohols were investigated by using Salmonella typhimurium TA1535, and Escherichia colt WP2uvrA tester strains at 0.01, 0.1, and 1 mu g/plate concentrations. (S)-4-aminoquinazoline alcohols were found to be genotoxically safe at the tested concentrations. Among the tested (S)-4-aminoquinazoline alcohols, the best antimutagenic activity was obtained with a methyl derivative at 0.1 mu g/plate dose. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.040

文献信息

• Synthesis of Chrysogine, a Metabolite of Penicillium chrysogenum and some related 2-substituted 4-(3H)-Quinazolinones
  作者：Jan Bergman、Anna Brynolf

  DOI：10.1016/s0040-4020(01)86694-1

  日期：1990.1

  Syntheses of both enantiomers of chrysogine, 2-(α-hydroxyethyl)-4(3H)-quinazolinone, 1 from 2-ammobenzamide are reported. Thus reaction of 2-aminobenzamide and optically active α-acetoxypropionyl chloride gave 9, which upon saponification and cyclization induced by aqueous sodium carbonate at room temperature gave chrysogine. The enantiomeric purity of 1 was determined by NMR. Inversion of (-)-(S)-1

  据报道，由2-氨苯甲酰胺合成了金葡胺的两种对映体2-（α-羟乙基）-4（3H）-喹唑啉酮1。因此，2-氨基苯甲酰胺与旋光性α-乙酰氧基丙酰氯的反应得到9，其在室温下由碳酸钠水溶液诱导的皂化和环化后得到金柳胺。通过NMR确定1的对映体纯度。使用Mitsunobo反应将（-）-（S）-1转化，得到（+）-（R）-1。的还原2 -乙酰基-4（3H）-qumazolinone 2与面包酵母，得到的S-对映体1。可以扩展使用的环化方法，并且还报道了许多2-（α-羟基）烷基-4-（3H）-喹唑啉酮。