methyl 1,3,7-trimethoxynaphthalene-2-carboxylate | 944936-91-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl 1,3,7-trimethoxynaphthalene-2-carboxylate
• 英文别名: methyl 1,3,7-trimethoxy-2-naphthoate
• CAS: 944936-91-8
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: YIYQHEAWUCQSLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 1,3,7-trimethoxynaphthalene-2-carboxylate 在 palladium(II) trifluoroacetate 氢氧化钾 、 三氟乙酸 作用下， 以 乙二醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1,3,7-trimethoxynaphthalene
  参考文献：
  名称：

  Development of a Catalytic Aromatic Decarboxylation Reaction

  摘要：

  A palladium-catalyzed aromatic decarboxylation reaction has been developed. With electron-rich aromatic acids, the reaction proceeds efficiently under fairly mild conditions in good yields. The method was useful with complex functionalized substrates containing hindered carboxylic acids.

  DOI：

  10.1021/ol070749f
• 作为产物：
  描述：

  硫酸二甲酯 、 methyl 1,3-dihydroxy-7-methoxynaphthalene-2-carboxylate 在 氢氧化钾 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以38%的产率得到methyl 1,3,7-trimethoxynaphthalene-2-carboxylate
  参考文献：
  名称：

  Development of a Catalytic Aromatic Decarboxylation Reaction

  摘要：

  A palladium-catalyzed aromatic decarboxylation reaction has been developed. With electron-rich aromatic acids, the reaction proceeds efficiently under fairly mild conditions in good yields. The method was useful with complex functionalized substrates containing hindered carboxylic acids.

  DOI：

  10.1021/ol070749f

文献信息

• Perylenequinone Natural Products: Evolution of the Total Synthesis of Cercosporin
  作者：Barbara J. Morgan、Carol A. Mulrooney、Marisa C. Kozlowski

  DOI：10.1021/jo9013854

  日期：2010.1.1

  The evolution of the First total synthesis of perylenequinone cercosporin is described. The key features developed during these efforts include a biscuprate epoxide alkylation, installation of the methylidene acetal, palladium-catalyzed O-arylation, and C3,C3'-decarbonylation. Due to the rapid atropisomerization of the helical axis of cercosporin (at 37 degrees C), the sequencing of these transformations was critical. To this end, the developed protocol enabled the formation of a key advanced intermediate oil preparative scale absent any atropisomerization. Furthermore, the O-arylation proved to be general, and the strategy was used in an improved synthesis of a helical chiral perylenequinone structure.