4-(4-methoxyphenyl)-1,3-dimethyl-3,7-dihydro-1H-furo[3,4-f]benzimidazole-2,5-dione | 1572419-17-0

• 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: 4-(4-methoxyphenyl)-1,3-dimethyl-3,7-dihydro-1H-furo[3,4-f]benzimidazole-2,5-dione
• CAS: 1572419-17-0
• 化学式: C₁₈H₁₆N₂O₄
• 分子量: 324.336
• InChiKey: MAFPOXZJQQVHAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  62.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3-benzyl-4-(4-methoxyphenyl)-3,7,7a,8-tetrahydro-5H-furo-[3,4-f]benzimidazol-5-one 在 manganese(IV) oxide 、 sodium hypochlorite 、 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 92.17h， 生成 4-(4-methoxyphenyl)-1,3-dimethyl-3,7-dihydro-1H-furo[3,4-f]benzimidazole-2,5-dione
  参考文献：
  名称：

  Total Synthesis of 7′-Desmethylkealiiquinone, 4′-Desmethoxykealiiquinone, and 2-Deoxykealiiquinone

  摘要：

  Synthetic approaches to the imidazonaphthoquinone core of kealiiquinone and related Leucetta-derived alkaloids are described. The polysubstituted benzimidazole framework can be constructed through intramolecular Diels-Alder reactions of propiolate-derived enynes followed by oxidation. Adjustment of the oxidation state of the thus formed lactone allows introduction of the 2,3-dihydroxybenzoquinone moiety through a presumed benzoin-like condensation between a phthaldehyde derivative and a masked glyoxal equivalent catalyzed by a cyanide ion. Oxidation of the C2-position can be accomplished through application of an operationally simple treatment of an imidazolium salt with bleach, thus producing the corresponding 2-imidazolone. Debenzylation of a late stage intermediate en route to kealiiquinone was compromised by concomitant O-demethylation upon treatment with triflic acid resulting in the formation of non-natural 7'-desmethylkealiiquinone. Other endgame strategies were evaluated; however, these efforts did not lead to completion of a synthesis of kealiiquinone but did provide access to other closely related analogues.

  DOI：

  10.1021/jo4027337