6-amino-7-methoxyisoquinoline-3-carboxylic acid methyl ester | 1453081-58-7

• 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: 6-amino-7-methoxyisoquinoline-3-carboxylic acid methyl ester
• 英文别名: Methyl 6-amino-7-methoxyisoquinoline-3-carboxylate
• CAS: 1453081-58-7
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: QLXIIXGBILIXQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-amino-7-methoxyisoquinoline-3-carboxylic acid methyl ester 在 次磷酸 、 溶剂黄146 、 sodium nitrite 作用下， 反应 2.5h， 以65%的产率得到methyl 7-methoxyisoquinoline-3-carboxylate
  参考文献：
  名称：

  Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone

  摘要：

  An alternative pathway for the biosynthesis of the fungal alkaloid necatorone has been studied using fluorine-labeled 3-(2-carboxyphenylamino)-L-tyrosine. Although no incorporation of this compound could be detected in feeding experiments with young specimens of Lactarius necator, an analogous 3-aminotyrosine derivative could be converted synthetically into the oxopyridoacridine core structure of necatorone. In experiments aimed at the synthesis of aaptamine-type alkaloids, an unprecedented cyclization of a 3-aminotyrosine-methyl propiolate adduct to a methyl isoquinoline-3-carboxylate was observed. A mechanism is proposed, in which C3 of the propiolate delivers C1 of the isoquinoline nucleus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.118
• 作为产物：
  描述：

  3-[5-(2-tert-butoxycarbonylamino-2-methoxycarbonylethyl)-2-methoxyphenylamino]acrylic acid methyl ester 在 苯酚 作用下， 反应 2.0h， 生成 6-amino-7-methoxyisoquinoline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Studies on the synthesis and biosynthesis of the fungal alkaloid necatorone

  摘要：

  An alternative pathway for the biosynthesis of the fungal alkaloid necatorone has been studied using fluorine-labeled 3-(2-carboxyphenylamino)-L-tyrosine. Although no incorporation of this compound could be detected in feeding experiments with young specimens of Lactarius necator, an analogous 3-aminotyrosine derivative could be converted synthetically into the oxopyridoacridine core structure of necatorone. In experiments aimed at the synthesis of aaptamine-type alkaloids, an unprecedented cyclization of a 3-aminotyrosine-methyl propiolate adduct to a methyl isoquinoline-3-carboxylate was observed. A mechanism is proposed, in which C3 of the propiolate delivers C1 of the isoquinoline nucleus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.118