dimethyl (1R,8S,9R,10S)-1-(cyanomethyl)-4,5-dimethoxy-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6-triene-9,10-dicarboxylate | 132234-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl (1R,8S,9R,10S)-1-(cyanomethyl)-4,5-dimethoxy-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6-triene-9,10-dicarboxylate
• CAS: 132234-16-3；132339-04-9；132339-05-0
• 化学式: C₁₈H₁₉NO₇
• 分子量: 361.351
• InChiKey: HZQAMSAADUEGMJ-ADAWSYLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  8

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 氢氧化钾 、 正丁基锂 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 生成 dimethyl (1R,8S,9R,10S)-1-(cyanomethyl)-4,5-dimethoxy-11-oxatricyclo[6.2.1.02,7]undeca-2,4,6-triene-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

文献信息

• 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.