2-Acetyl-4,5-dimethoxybenzaldehyde | 132234-11-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Acetyl-4,5-dimethoxybenzaldehyde
• CAS: 132234-11-8
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: OZGCOMKJDDZCMH-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  371.3±42.0 °C(predicted)
• 密度：
  1.152±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-溴-2-(二甲氧基甲基)-4,5-二甲氧基苯 在 sodium hydroxide 、 正丁基锂 、 溶剂黄146 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 27.25h， 生成 2-Acetyl-4,5-dimethoxybenzaldehyde
  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

文献信息

• Broeck, Peter I. Van; Vanderzande, Dirk J.; Kiekens, Eric G., Journal of the Chemical Society. Perkin transactions I, 1991, # 3, p. 639 - 644
  作者：Broeck, Peter I. Van、Vanderzande, Dirk J.、Kiekens, Eric G.、Hoornaert, Georges J.

  DOI：——

  日期：——
• MEEGALLA, SANATH K.;RODRIGO, RUSSELL, J. ORG. CHEM., 56,(1991) N, C. 1882-1888
  作者：MEEGALLA, SANATH K.、RODRIGO, RUSSELL

  DOI：——

  日期：——
• A general synthetic route to isobenzofurans bearing a functionalized C-1 substituent
  作者：Sanath K. Meegalla、Russell Rodrigo

  DOI：10.1021/jo00005a040

  日期：1991.3

  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.