acetic acid 4-oxo-3-prop-2-ynyl-3,4-dihydroquinazolin-2-ylmethyl ester | 823235-10-5

• 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: acetic acid 4-oxo-3-prop-2-ynyl-3,4-dihydroquinazolin-2-ylmethyl ester
• 英文别名: 4(3H)-Quinazolinone, 2-[(acetyloxy)methyl]-3-(2-propynyl)-；(4-oxo-3-prop-2-ynylquinazolin-2-yl)methyl acetate
• CAS: 823235-10-5
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: JUDKEYCCMONCPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  acetic acid 4-oxo-3-prop-2-ynyl-3,4-dihydroquinazolin-2-ylmethyl ester 在 吡啶 、 sodium hydroxide 、 水 、 戴斯-马丁氧化剂 、 dysprosium(III) trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.0h， 生成 色氨酸A
  参考文献：
  名称：

  Intramolecular Hetero Diels−Alder (Povarov) Approach to the Synthesis of the Alkaloids Luotonin A and Camptothecin

  摘要：

  Pyrrolo[3,4-b]quinolines can be formed through the coupling of anilines with N-propargylic substituted heterocyclic aldehydes in the presence of mild Lewis acid catalysts (Ln(OTf)(3)). The coupling proceeds through sequential imine formation and a formal intramolecular aza-Diels-Alder (Povarov) reaction. This approach was applied in a total synthesis of luotonin A and a formal synthesis of camptothecin.

  DOI：

  10.1021/ol0479848
• 作为产物：
  描述：

  acetic acid 4-prop-2-ynylimino-4H-benzo[d][1,3]oxazin-2-ylmethyl ester 在 哌啶 、 silica gel 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以85%的产率得到acetic acid 4-oxo-3-prop-2-ynyl-3,4-dihydroquinazolin-2-ylmethyl ester
  参考文献：
  名称：

  Intramolecular Hetero Diels−Alder (Povarov) Approach to the Synthesis of the Alkaloids Luotonin A and Camptothecin

  摘要：

  Pyrrolo[3,4-b]quinolines can be formed through the coupling of anilines with N-propargylic substituted heterocyclic aldehydes in the presence of mild Lewis acid catalysts (Ln(OTf)(3)). The coupling proceeds through sequential imine formation and a formal intramolecular aza-Diels-Alder (Povarov) reaction. This approach was applied in a total synthesis of luotonin A and a formal synthesis of camptothecin.

  DOI：

  10.1021/ol0479848

文献信息

• Intramolecular Hetero Diels−Alder (Povarov) Approach to the Synthesis of the Alkaloids Luotonin A and Camptothecin
  作者：Heather Twin、Robert A. Batey

  DOI：10.1021/ol0479848

  日期：2004.12.1

  Pyrrolo[3,4-b]quinolines can be formed through the coupling of anilines with N-propargylic substituted heterocyclic aldehydes in the presence of mild Lewis acid catalysts (Ln(OTf)(3)). The coupling proceeds through sequential imine formation and a formal intramolecular aza-Diels-Alder (Povarov) reaction. This approach was applied in a total synthesis of luotonin A and a formal synthesis of camptothecin.