5,6,8-trimethoxyquinoline-2-carboxylic acid methyl ester | 957785-10-3

• 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: 5,6,8-trimethoxyquinoline-2-carboxylic acid methyl ester
• 英文别名: Methyl 5,6,8-trimethoxyquinoline-2-carboxylate
• CAS: 957785-10-3
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: XSRDZSSXEUQNTR-UHFFFAOYSA-N

物化性质

• 熔点：
  164-165.5 °C
• 沸点：
  427.7±40.0 °C(predicted)
• 密度：
  1.223±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6,8-trimethoxyquinoline-2-carboxylic acid methyl ester 在 sodium hydroxide 、 potassium tert-butylate 、 一氯化碘 、 sodium hydride 、 potassium carbonate 、 silver carbonate 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 138.0h， 生成 2-[5,6,8-trimethoxy-2-quinolinyl]-4-[3,4-dimethoxy-2-(phenylmethoxy)phenyl]-6-benzyloxy-5-methyl-3-iodopyridine
  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：

  4-chloro-5,6,8-trimethoxyquinoline-2-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 0.75h， 以100%的产率得到5,6,8-trimethoxyquinoline-2-carboxylic acid methyl ester
  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.