2-(2,4-dinitrophenyl)-1-(2-ethoxy-2-methoxyethyl)-4-prop-2-enoxy-1H-isoquinoline | 170507-77-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2,4-dinitrophenyl)-1-(2-ethoxy-2-methoxyethyl)-4-prop-2-enoxy-1H-isoquinoline
• CAS: 170507-77-4
• 化学式: C₂₃H₂₅N₃O₇
• 分子量: 455.467
• InChiKey: HPFPUSJMZSOBTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(2,4-dinitrophenyl)-1-(2-ethoxy-2-methoxyethyl)-4-prop-2-enoxy-1H-isoquinoline 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 endo-7-Ethoxy-6,7,8,9-tetrahydro-10-(2,4-dinitrophenyl)-9-oxo-5H-benzocyclohepten-5,8-imine 、 exo-7-Methoxy-6,7,8,9-tetrahydro-10-(2,4-dinitrophenyl)-9-oxo-5H-benzocyclohepten-5,8-imine 、 endo-7-Methoxy-6,7,8,9-tetrahydro-10-(2,4-dinitrophenyl)-9-oxo-5H-benzocyclohepten-5,8-imine
  参考文献：
  名称：

  Bradsher Cycloaddition of 4-Alkoxyisoquinolinium Salts as a Route to a Fully Functionalized B Ring of the Angucycline Antibiotics

  摘要：

  The title cycloaddition leads to a more complicated reaction manifold when there is an alkoxy group at C-4 of the isoquinoline salt. Whereas the earlier unsubstituted isoquinoline salts afforded materials from 1,4 cycloaddition, in the present examples, 1,4 and 1,3 cycloaddults are observed. Both simple and alkoxylated substrates yielded one-bond noncycloadduct materials. Careful product analysis suggests that the general mechanistic principles of the Bradsher reaction can account for all the observations in the alkoxyisoquinoline reactions. Cycloadduct 22 was carried through a short sequence to acetal 44, the first synthetic model for the 1-acyl-cis-1,2-dialkoxy-1,2-dihydronaphthalene framework of the sakyomicin class of the angucycline antibiotics.

  DOI：

  10.1021/jo00126a048
• 作为产物：
  描述：

  乙烯基乙醚 、 2-(2,4-Dinitrophenyl)-4-(allyloxy)isoquinolinium chloride 在 silica gel 、 calcium carbonate 作用下， 生成 endo-7-Ethoxy-6,7,8,9-tetrahydro-10-(2,4-dinitrophenyl)-9-oxo-5H-benzocyclohepten-5,8-imine 、 、 2-(2,4-dinitrophenyl)-1-(2-ethoxy-2-methoxyethyl)-4-prop-2-enoxy-1H-isoquinoline
  参考文献：
  名称：

  Bradsher Cycloaddition of 4-Alkoxyisoquinolinium Salts as a Route to a Fully Functionalized B Ring of the Angucycline Antibiotics

  摘要：

  The title cycloaddition leads to a more complicated reaction manifold when there is an alkoxy group at C-4 of the isoquinoline salt. Whereas the earlier unsubstituted isoquinoline salts afforded materials from 1,4 cycloaddition, in the present examples, 1,4 and 1,3 cycloaddults are observed. Both simple and alkoxylated substrates yielded one-bond noncycloadduct materials. Careful product analysis suggests that the general mechanistic principles of the Bradsher reaction can account for all the observations in the alkoxyisoquinoline reactions. Cycloadduct 22 was carried through a short sequence to acetal 44, the first synthetic model for the 1-acyl-cis-1,2-dialkoxy-1,2-dihydronaphthalene framework of the sakyomicin class of the angucycline antibiotics.

  DOI：

  10.1021/jo00126a048

文献信息

• Bradsher Cycloaddition of 4-Alkoxyisoquinolinium Salts as a Route to a Fully Functionalized B Ring of the Angucycline Antibiotics
  作者：Tony E. Nicolas、Richard W. Franck

  DOI：10.1021/jo00126a048

  日期：1995.10

  The title cycloaddition leads to a more complicated reaction manifold when there is an alkoxy group at C-4 of the isoquinoline salt. Whereas the earlier unsubstituted isoquinoline salts afforded materials from 1,4 cycloaddition, in the present examples, 1,4 and 1,3 cycloaddults are observed. Both simple and alkoxylated substrates yielded one-bond noncycloadduct materials. Careful product analysis suggests that the general mechanistic principles of the Bradsher reaction can account for all the observations in the alkoxyisoquinoline reactions. Cycloadduct 22 was carried through a short sequence to acetal 44, the first synthetic model for the 1-acyl-cis-1,2-dialkoxy-1,2-dihydronaphthalene framework of the sakyomicin class of the angucycline antibiotics.