(S)-1-(4-chloroquinazolin-2-yl)ethyl acetate | 1251849-64-5

• 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)-1-(4-chloroquinazolin-2-yl)ethyl acetate
• 英文别名: [(1S)-1-(4-chloroquinazolin-2-yl)ethyl] acetate
• CAS: 1251849-64-5
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: LXRJFIAWPFQORL-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-chloroquinazolin-2-yl)ethyl acetate 在 氨 、 水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成
  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)-1-(4-oxo-3,4-dihydroquinazolin-2-yl)ethyl acetate 在 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 苯 为溶剂， 以97%的产率得到(S)-1-(4-chloroquinazolin-2-yl)ethyl 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 and Catalytic Asymmetric Applications of Quinazolinol Ligands
  作者：Sabri Ulukanli、Idris Karakaya、Semistan Karabuga、Mehmet Mart、Ramazan Altundas

  DOI：10.1055/s-0035-1561584

  日期：——

  range of chiral quinazolinol ligands were efficiently synthesized and subsequently investigated for catalytic chiral induction in both the asymmetric phenylation of aryl aldehydes and the asymmetric epoxidation of chalcones. Encouragingly, high enantioselectivities (up to 95%) and yields (up to 98%) were achieved under the optimized reaction conditions. A range of chiral quinazolinol ligands were efficiently

  摘要 有效地合成了一系列手性喹唑啉醇配体，随后研究了其在芳基醛的不对称苯基化和查耳酮的不对称环氧化中的催化手性诱导作用。令人鼓舞的是，在优化的反应条件下，实现了高对映选择性（最高95％）和产率（最高98％）。 有效地合成了一系列手性喹唑啉醇配体，随后研究了其在芳基醛的不对称苯基化和查耳酮的不对称环氧化中的催化手性诱导作用。令人鼓舞的是，在优化的反应条件下，实现了高对映选择性（最高95％）和产率（最高98％）。
• Synthesis of quinazoline based chiral ligands and application in the enantioselective addition of phenylacetylene to aldehydes
  作者：Idris Karakaya、Semistan Karabuga、Ramazan Altundas、Sabri Ulukanli

  DOI：10.1016/j.tet.2014.08.067

  日期：2014.11

  Five novel 4-phenylquinazolinols were synthesised in three steps. Their application as ligands in the titanium tetraisopropoxide promoted catalytic enantioselective addition of phenylacetylene to a variety of aldehydes gave propargylic alcohols. Under the optimised reaction conditions, the best enantioselectivity was obtained using L-lactic acid derived 4-phenylquinazolinol and apart from the cyclohexylcarbaldehyde derivative, 16 propargylic alcohols were then synthesised in moderate to excellent enantiomeric excess from 53% to 97%. (C) 2014 Elsevier Ltd. All rights reserved.