Methyl 4-nitro-4-(3,5,6-trimethoxy-1,3-dihydro-2-benzofuran-1-yl)pentanoate | 132234-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: Methyl 4-nitro-4-(3,5,6-trimethoxy-1,3-dihydro-2-benzofuran-1-yl)pentanoate
• CAS: 132234-09-4
• 化学式: C₁₇H₂₃NO₈
• 分子量: 369.372
• InChiKey: OTMYSOYUXQHVEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 4-nitro-4-(3,5,6-trimethoxy-1,3-dihydro-2-benzofuran-1-yl)pentanoate 在 偶氮二异丁腈 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 Dimethyl 4,5-dimethoxy-1-(5-methoxy-5-oxopentan-2-yl)-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：

  4,5-dimethoxy-2-(dimethoxymethyl)benzaldehyde 在 ammonium acetate 、 sodium acetate 、 苄基三甲基氢氧化铵 、 叔丁醇 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 22.03h， 生成 Methyl 4-nitro-4-(3,5,6-trimethoxy-1,3-dihydro-2-benzofuran-1-yl)pentanoate
  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：——