3,5,8-triacetoxyisoquinoline | 80662-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3,5,8-triacetoxyisoquinoline
• 英文别名: (3,8-Diacetyloxyisoquinolin-5-yl) acetate
• CAS: 80662-18-6
• 化学式: C₁₅H₁₃NO₆
• 分子量: 303.271
• InChiKey: BWIWRQOWBBQVSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.79
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  甲亚胺酸,N-[1-[[(1,1-二甲基乙基)二甲基甲硅烷基]氧代]乙烯基]-,(1,1-二甲基乙基)二甲基甲硅烷基酯,(1E)- 、 对苯醌 、 乙酸酐 在 吡啶 作用下， 生成 3,5,8-triacetoxyisoquinoline
  参考文献：
  名称：

  A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy

  摘要：

  :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01149-1

文献信息

• A Diels-Alder route to pyridone and piperidone derivatives
  作者：Francy Sainte、Beatrice Serckx-Poncin、Anne Marie Hesbain-Frisque、Leon Ghosez

  DOI：10.1021/ja00369a049

  日期：1982.3
• SAINTE, F.;SERCKS-PONCIN, B.;HESBAIN-FRISQUE, A. -M.;GHOSEZ, L., J. AMER. CHEM. SOC., 1982, 104, N 5, 1428-1430
  作者：SAINTE, F.、SERCKS-PONCIN, B.、HESBAIN-FRISQUE, A. -M.、GHOSEZ, L.

  DOI：——

  日期：——
• A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy
  作者：Lon Ghosez、Eric Jnoff、Philippe Bayard、Francy Sainte、Renaud Beaudegnies

  DOI：10.1016/s0040-4020(98)01149-1

  日期：1999.3

  :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.