1-Hydroxy-6,7-dimethoxy-4-nitromethyl-naphthalene-2,3-dicarboxylic acid dimethyl ester | 132234-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Hydroxy-6,7-dimethoxy-4-nitromethyl-naphthalene-2,3-dicarboxylic acid dimethyl ester
• CAS: 132234-08-3
• 化学式: C₁₇H₁₇NO₉
• 分子量: 379.323
• InChiKey: BDYFEFSHUUBGHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  134.43
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  4,5-dimethoxy-2-(dimethoxymethyl)benzaldehyde 在 sodium hydroxide 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 12.25h， 生成 1-Hydroxy-6,7-dimethoxy-4-nitromethyl-naphthalene-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  A general synthetic route to isobenzofurans bearing a functionalized C-1 substituent

  摘要：

  Aromatic o-formyl acetals undergo base-catalyzed Claisen-Schmidt condensation with nitro compounds, ketones, methyl acetate, and acetonitrile to produce functionalized styrenes. Hydrolysis of the acetal and cyclization of the product in methanol provide methoxy phthalans 8 which are used to generate isobenzofurans bearing a functionalized substituent at C-1. The Diels-Alder reactions of these isobenzofurans with several dienophiles have been studied. Conjugated exo-methylene phthalans 20 have been isolated, and an unusual elimination of nitrous acid from nitroalkyl phthalans 8E and 8F has been observed.

  DOI：

  10.1021/jo00005a040