Ethyl 3-oxo-3-(5,6,8-trimethoxyquinolin-2-yl)propanoate | 957785-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Ethyl 3-oxo-3-(5,6,8-trimethoxyquinolin-2-yl)propanoate
• CAS: 957785-19-2
• 化学式: C₁₇H₁₉NO₆
• 分子量: 333.341
• InChiKey: DYOOREKYRLFZNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 3-oxo-3-(5,6,8-trimethoxyquinolin-2-yl)propanoate 、 3,4-dimethoxy-(phenylmethoxy)benzaldehyde 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 0.58h， 以49.3%的产率得到Ethyl 1-(3,4-dimethoxy-2-phenylmethoxyphenyl)-3-hydroxy-6,7,9-trimethoxypyrrolo[1,2-a]quinoline-2-carboxylate
  参考文献：
  名称：

  Total Synthesis of Streptonigrone

  摘要：

  A total synthesis of streptonigrone, 1, is described, which incorporates a one-step synthesis of substituted pyridones devised in our laboratory. Other aspects of the synthesis that differentiate the present approach from previous ones are the use of a Conrad - Limpach reaction, rather than the customary Friedlander methodology, to assemble the quinoline segment of 1, and the implementation of an anionic sequence for the functionalization of a key pyridone intermediate.

  DOI：

  10.1021/jo701435p
• 作为产物：
  描述：

  2-[(2,4,5-trimethoxyphenyl)amino]-2-butenedioic acid dimethyl ester 在 palladium on activated charcoal 氢气 、 sodium hydride 、 三乙胺 、 三氯氧磷 作用下， 以 二苯醚 、 乙酸乙酯 、 甲苯 、 苯 为溶剂， 反应 41.75h， 生成 Ethyl 3-oxo-3-(5,6,8-trimethoxyquinolin-2-yl)propanoate
  参考文献：
  名称：

  Total Synthesis of Streptonigrone

  摘要：

  A total synthesis of streptonigrone, 1, is described, which incorporates a one-step synthesis of substituted pyridones devised in our laboratory. Other aspects of the synthesis that differentiate the present approach from previous ones are the use of a Conrad - Limpach reaction, rather than the customary Friedlander methodology, to assemble the quinoline segment of 1, and the implementation of an anionic sequence for the functionalization of a key pyridone intermediate.

  DOI：

  10.1021/jo701435p

文献信息

• Total Synthesis of Streptonigrone
  作者：Bryan K. Chan、Marco A. Ciufolini

  DOI：10.1021/jo701435p

  日期：2007.10.1

  A total synthesis of streptonigrone, 1, is described, which incorporates a one-step synthesis of substituted pyridones devised in our laboratory. Other aspects of the synthesis that differentiate the present approach from previous ones are the use of a Conrad - Limpach reaction, rather than the customary Friedlander methodology, to assemble the quinoline segment of 1, and the implementation of an anionic sequence for the functionalization of a key pyridone intermediate.