3-Ethoxycarbonylmethyl-6,8-dihydroxy-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester | 141501-52-2

• 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-Ethoxycarbonylmethyl-6,8-dihydroxy-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester
• 英文别名: ethyl 3-(2-ethoxy-2-oxoethyl)-6,8-dihydroxy-1-oxo-2H-isoquinoline-4-carboxylate
• CAS: 141501-52-2
• 化学式: C₁₆H₁₇NO₇
• 分子量: 335.313
• InChiKey: HYPWAIBPKCLCON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-Acetyl-2,4-bis-ethoxycarbonylmethyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以75%的产率得到3-Ethoxycarbonylmethyl-6,8-dihydroxy-1-oxo-1,2-dihydro-isoquinoline-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  A Versatile New Method for Synthesis of Isoquinolines; 6,8-Dihydroxyisoquinoline Derivatives from 6-Methyl-1,3-oxazin-4-ones

  摘要：

  A versatile method for synthesis of isoquinolone derivatives (4a-h) from 2-substituted 6-methyl-4H-1,3-oxazin-4-ones (1a-h) is described. Transformation of 1a-h with diethyl acetonedicarboxylate (2) in the presence of potassium tert-butoxide afforded 6-substituted 3-acetyl-5-ethoxycarbonyl-4-ethoxycarbonylmethylene-2-pyridones (3a-h) in excellent yields. Dieckmann-type cyclization of 3a-h with sodium ethoxide in ethanol produced the corresponding isoquinolone derivatives (4a-h) in good yields, respectively.

  DOI：

  10.3987/com-91-s75

文献信息

• [EN] ISOCARBOSTIRYL COMPOUNDS AND ANTITUMOR USE THEREOF
  申请人：SYNPHAR LABORATORIES, INC.

  公开号：WO1992003419A1

  公开（公告）日：1992-03-05

  (EN) Alkyl 3-substituted-6,8-dihydroxy-1(2H)-oxoisoquinoline-4-carboxylates, such as ethyl 6,8-dihydroxy-3-phenyl-1(2H)-oxoisoquinoline-4-carboxylate, exhibit cytotoxicity against a wide variety of tumor cell lines, and can thus be used to treat cancer such as leukemias and carcinomas.(FR) 3-substitué-6,8-dihydroxy-1(2H)-oxoisoquinoléine-4-carboxylates d'alkyle, par exemple 6,8-dihydroxy-3-phényle-1(2H)-oxoisoquinoléine-4-carboxylate d'éthyle, présente une cytotoxicité dirigée contre une grande diversité de lignées de cellules tumorales, et peuvent donc s'utiliser pour le traitement des cancers, par exemple les leucémies et les carcinomes.
• A Versatile New Method for Synthesis of Isoquinolines; 6,8-Dihydroxyisoquinoline Derivatives from 6-Methyl-1,3-oxazin-4-ones
  作者：Yutaka Yamamoto、Yasuo Morita、Osamu Ohmukai

  DOI：10.3987/com-91-s75

  日期：——

  A versatile method for synthesis of isoquinolone derivatives (4a-h) from 2-substituted 6-methyl-4H-1,3-oxazin-4-ones (1a-h) is described. Transformation of 1a-h with diethyl acetonedicarboxylate (2) in the presence of potassium tert-butoxide afforded 6-substituted 3-acetyl-5-ethoxycarbonyl-4-ethoxycarbonylmethylene-2-pyridones (3a-h) in excellent yields. Dieckmann-type cyclization of 3a-h with sodium ethoxide in ethanol produced the corresponding isoquinolone derivatives (4a-h) in good yields, respectively.