3-benzyl-6,7-dihydroxy-4-phenyl-1H-naphtho[2,3-d]imidazole-5,8-dione | 1572418-99-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-benzyl-6,7-dihydroxy-4-phenyl-1H-naphtho[2,3-d]imidazole-5,8-dione
• CAS: 1572418-99-5
• 化学式: C₂₄H₁₆N₂O₄
• 分子量: 396.402
• InChiKey: SEUYJMHPTQXYII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  92.42
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-benzyl-6,7-dihydroxy-4-phenyl-1H-naphtho[2,3-d]imidazole-5,8-dione 在 三甲基硅烷化重氮甲烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 以54%的产率得到3-benzyl-6,7-dimethoxy-4-phenyl-1H-naphtho[2,3-d]imidazole-5,8-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
• 作为产物：
  描述：

  [3-benzyl-4-phenyl-1H-benzimidazole-5,6-diyl]dimethanol 在 potassium cyanide 、 N-叔丁基苯硫腈氯化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.75h， 生成 3-benzyl-6,7-dihydroxy-4-phenyl-1H-naphtho[2,3-d]imidazole-5,8-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