2-[(1S)-1-hydroxyethyl]-3-{(3R)-3-[(1R)-1-hydroxyethyl]-2,2-dimethylaziridin-1-yl}quinazolin-4(3H)-one

• 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: 2-[(1S)-1-hydroxyethyl]-3-{(3R)-3-[(1R)-1-hydroxyethyl]-2,2-dimethylaziridin-1-yl}quinazolin-4(3H)-one
• 英文别名: 2-[(1S)-1-hydroxyethyl]-3-[(3R)-3-[(1R)-1-hydroxyethyl]-2,2-dimethylaziridin-1-yl]quinazolin-4-one
• 化学式: C₁₆H₂₁N₃O₃
• 分子量: 303.361
• InChiKey: ASPUCQYFQYDLFI-MPJSESDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-3-amino-2-(1-hydroxyethyl)quinazolin-4(3H)-one 在 sodium tetrahydroborate 、 碘苯二乙酸 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-[(1S)-1-hydroxyethyl]-3-{(3R)-3-[(1R)-1-hydroxyethyl]-2,2-dimethylaziridin-1-yl}quinazolin-4(3H)-one 、 2-[(1S)-1-hydroxyethyl]-3-{(3R)-3-[(1S)-1-hydroxyethyl]-2,2-dimethylaziridin-1-yl}quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes

  摘要：

  A new class of quinazoline-based enantiomerically pure aziridine diols 4a-d were prepared from the aziridination of mesityl oxide 3 with in situ generated 3-acetoxyaminoquinazolinone (S)-2b followed by NaBH4 reduction. Aziridine diols 4a-d were purified by means of column chromatography on silica gel and their stereochemistries were assigned by X-ray crystallography and NMR analysis. These aziridine diols 4 were evaluated as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes, and ligand (S,R,R)-4a yielded (R)-1-phenylpropanol derivatives with up to 92% ee, while the diastereomer (S,S,R)-4c gave the opposite enantiomers (S)-1-phenylpropanol derivatives with up to 86% ee. The results demonstrate that switching the configuration of the aziridine alcohol moiety in ligand gives a remarkable reversal of enantioselectivity in the asymmetric addition of diethylzinc to aryl aldehydes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.12.011
• 作为试剂：
  描述：

  间溴苯甲醛 、 diethylzinc 在 2-[(1S)-1-hydroxyethyl]-3-{(3R)-3-[(1R)-1-hydroxyethyl]-2,2-dimethylaziridin-1-yl}quinazolin-4(3H)-one 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 48.0h， 以70%的产率得到
  参考文献：
  名称：

  Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes

  摘要：

  A new class of quinazoline-based enantiomerically pure aziridine diols 4a-d were prepared from the aziridination of mesityl oxide 3 with in situ generated 3-acetoxyaminoquinazolinone (S)-2b followed by NaBH4 reduction. Aziridine diols 4a-d were purified by means of column chromatography on silica gel and their stereochemistries were assigned by X-ray crystallography and NMR analysis. These aziridine diols 4 were evaluated as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes, and ligand (S,R,R)-4a yielded (R)-1-phenylpropanol derivatives with up to 92% ee, while the diastereomer (S,S,R)-4c gave the opposite enantiomers (S)-1-phenylpropanol derivatives with up to 86% ee. The results demonstrate that switching the configuration of the aziridine alcohol moiety in ligand gives a remarkable reversal of enantioselectivity in the asymmetric addition of diethylzinc to aryl aldehydes. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.12.011

文献信息

• Synthesis of quinazolinone-based aziridine diols as chiral ligands: dual stereoselectivity in the asymmetric ethylation of aryl aldehydes
  作者：Saffet Celik、Murat Cakici、Hamdullah Kilic、Ertan Sahin

  DOI：10.1016/j.tetasy.2014.12.011

  日期：2015.2

  A new class of quinazoline-based enantiomerically pure aziridine diols 4a-d were prepared from the aziridination of mesityl oxide 3 with in situ generated 3-acetoxyaminoquinazolinone (S)-2b followed by NaBH4 reduction. Aziridine diols 4a-d were purified by means of column chromatography on silica gel and their stereochemistries were assigned by X-ray crystallography and NMR analysis. These aziridine diols 4 were evaluated as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes, and ligand (S,R,R)-4a yielded (R)-1-phenylpropanol derivatives with up to 92% ee, while the diastereomer (S,S,R)-4c gave the opposite enantiomers (S)-1-phenylpropanol derivatives with up to 86% ee. The results demonstrate that switching the configuration of the aziridine alcohol moiety in ligand gives a remarkable reversal of enantioselectivity in the asymmetric addition of diethylzinc to aryl aldehydes. (C) 2015 Elsevier Ltd. All rights reserved.