2-hydroxymethyl-3-prop-2-ynyl-3H-quinazolin-4-one | 823235-13-8

• 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-hydroxymethyl-3-prop-2-ynyl-3H-quinazolin-4-one
• 英文别名: 2-(Hydroxymethyl)-3-(prop-2-yn-1-yl)quinazolin-4(3H)-one；2-(hydroxymethyl)-3-prop-2-ynylquinazolin-4-one
• CAS: 823235-13-8
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: MOICXSQMJLJLSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-3-prop-2-ynyl-3H-quinazolin-4-one 在 吡啶 、 戴斯-马丁氧化剂 、 dysprosium(III) trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 29.0h， 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-oxo-3-prop-2-ynyl-3,4-dihydroquinazolin-2-ylmethyl ester 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以83%的产率得到2-hydroxymethyl-3-prop-2-ynyl-3H-quinazolin-4-one
  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.