1-(4',5'-dimethoxy-2'-formylphenyl)hepta-1,6-dien-3-one | 132233-81-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-(4',5'-dimethoxy-2'-formylphenyl)hepta-1,6-dien-3-one
• 英文别名: 4,5-dimethoxy-2-[(1E)-3-oxohepta-1,6-dienyl]benzaldehyde
• CAS: 132233-81-9
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: HBOLKSXAWPMWJY-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4',5'-dimethoxy-2'-formylphenyl)hepta-1,6-dien-3-one 在 sodium acetate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Dimethyl 4,5-dimethoxy-1-(2-oxohex-5-enyl)-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6,9-tetraene-9,10-dicarboxylate
  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
• 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 作用下， 反应 10.0h， 生成 1-(4',5'-dimethoxy-2'-formylphenyl)hepta-1,6-dien-3-one
  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

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

  DOI：——

  日期：——