2-deoxykealiiquinone | 1373395-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-deoxykealiiquinone
• 英文别名: 6,7-dimethoxy-4-(4-methoxyphenyl)-1-methyl-1H-naphtho-[2,3-d]imidazole-5,8-dione；6,7-Dimethoxy-4-(4-methoxyphenyl)-1-methylbenzo[f]benzimidazole-5,8-dione；6,7-dimethoxy-4-(4-methoxyphenyl)-1-methylbenzo[f]benzimidazole-5,8-dione
• CAS: 1373395-19-7
• 化学式: C₂₁H₁₈N₂O₅
• 分子量: 378.384
• InChiKey: BPQZWCILIAWVSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲醇 、 6,7-dihydroxy-4-(4-methoxyphenyl)-1-methyl-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 1.0h， 以64%的产率得到2-deoxykealiiquinone
  参考文献：
  名称：

  7'-去甲基酮基醌的全合成

  摘要：

  通过应用含咪唑烯炔的分子内 Diels-Alder 反应，完成了海洋生物碱 kealiiquinone 类似物的全合成。内酯加合物的氧化芳构化和N-甲基化通过咪唑鎓盐促进 C2-氧化。通过在 KCN 存在下与乙二醛反应，实现内酯向苯二醛衍生物的转化，然后转化为二羟基苯醌。乙烯基二酸的酯化和脱保护提供了 7'-去甲基酮基醌。

  DOI：

  10.1021/ol300704w

文献信息

• Total Synthesis of 7′-Desmethylkealiiquinone
  作者：Heather M. Lima、Rasapalli Sivappa、Muhammed Yousufuddin、Carl J. Lovely

  DOI：10.1021/ol300704w

  日期：2012.5.4

  The total synthesis of an analogue of the marine alkaloid kealiiquinone has been completed through application of an intramolecular Diels–Alder reaction of an imidazole-containing enyne. Oxidative aromatization of the lactone adduct and N-methylation facilitates C2-oxidation via the imidazolium salt. Conversion of the lactone to the phthalaldehyde derivative and then to the dihydroxybenzoquinone was

  通过应用含咪唑烯炔的分子内 Diels-Alder 反应，完成了海洋生物碱 kealiiquinone 类似物的全合成。内酯加合物的氧化芳构化和N-甲基化通过咪唑鎓盐促进 C2-氧化。通过在 KCN 存在下与乙二醛反应，实现内酯向苯二醛衍生物的转化，然后转化为二羟基苯醌。乙烯基二酸的酯化和脱保护提供了 7'-去甲基酮基醌。
• Total syntheses and cytotoxicity of kealiiquinone, 2-deoxy-2-aminokealiiquinone and analogs
  作者：Jayanta Das、Arunoday Bhan、Subhrangsu S. Mandal、Carl J. Lovely

  DOI：10.1016/j.bmcl.2013.08.093

  日期：2013.11

  Concise syntheses of two Leucetta-derived naphthimidazole alkaloids, kealiiquinone and 2-deoxy-2-aminokealiiquinone, are described based on a biosynthetic-guided hypothesis. Advanced intermediates containing the full naphthimidazole framework are constructed through Friedel-Crafts chemistry followed by oxidation of the electron rich C-ring with hydrogen peroxide. The cytotoxicity of these alkaloids in a breast cancer cell line along with several closely related marine-derived natural products kealiinines A-C and analogs are reported. (c) 2013 Elsevier Ltd. All rights reserved.
• Total Synthesis of 7′-Desmethylkealiiquinone, 4′-Desmethoxykealiiquinone, and 2-Deoxykealiiquinone
  作者：Heather M. Lima、Rasapalli Sivappa、Muhammed Yousufuddin、Carl J. Lovely

  DOI：10.1021/jo4027337

  日期：2014.3.21

  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.