2-(1-tert-Butoxycarbonyl-1H-indol-3-yl)-(4-hydroxy-1H-indol-3-yl)-1-methyl-2,5-dihydro-2,5-dioxopyrrole | 179632-29-2

• 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: 2-(1-tert-Butoxycarbonyl-1H-indol-3-yl)-(4-hydroxy-1H-indol-3-yl)-1-methyl-2,5-dihydro-2,5-dioxopyrrole
• 英文别名: tert-butyl 3-[4-(4-hydroxy-1H-indol-3-yl)-1-methyl-2,5-dioxopyrrol-3-yl]indole-1-carboxylate
• CAS: 179632-29-2
• 化学式: C₂₆H₂₃N₃O₅
• 分子量: 457.486
• InChiKey: LEWSEPGXPOGHBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1-tert-Butoxycarbonyl-1H-indol-3-yl)-(4-hydroxy-1H-indol-3-yl)-1-methyl-2,5-dihydro-2,5-dioxopyrrole 在 palladium diacetate 4-二甲氨基吡啶 、 1,3-双(二苯基膦)丙烷 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N-Methylarcyriacyanin
  参考文献：
  名称：

  Total syntheses of the slime mold alkaloid arcyriacyanin A

  摘要：

  AbstractArcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4′‐biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4‐(triflyloxy)arcyriarubin 8 to N‐methylarcyriacyanin A (2). Thirdly, compound 2 was obtained by a domino Heck reaction between 3‐bromo‐4‐[1‐(tert‐butoxycarbonyl)indol‐3‐yl]‐1‐methylmaleimide (9) and 4‐bromoindole (10). The N‐methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.

  DOI：

  10.1002/chem.19970030112
• 作为产物：
  描述：

  tert-butyl 3-(4-bromo-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole-1-carboxylate 在 Amberlite 15 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 2-(1-tert-Butoxycarbonyl-1H-indol-3-yl)-(4-hydroxy-1H-indol-3-yl)-1-methyl-2,5-dihydro-2,5-dioxopyrrole
  参考文献：
  名称：

  阿霉素A的全合成

  摘要：

  通过酸催化的双吲哚基马来酰亚胺衍生物7合成了煤泥霉菌生物碱阿曲霉素A（1）。

  DOI：

  10.1016/0040-4039(96)00864-7

文献信息

• Total Synthesis of the Slime Mold Alkaloids Arcyroxocin A and B
  作者：Wolfgang Steglich、Guido Mayer、Gregor Wille、Michael Brenner、Kirsten Zeitler

  DOI：10.1055/s-0030-1258340

  日期：2011.1

  The synthesis of the slime mold pigments arcyroxocin A and B is described. The key step in the synthesis is the oxidative ring closure of an N-protected 3-(4-hydroxyindol-3-yl)-4-indol-3-ylmaleimide with DDQ/PPTS, which affords exclusively the desired arcyroxocin derivative. Attempts to obtain the arcyroxocin system from a 3-(4-hydroxyindolyl)-4-(2-oxoindolinyl)maleimide precursor were less successful

  描述了粘液霉菌颜料阿霉素A和B的合成。合成中的关键步骤是N-保护的3-（4-羟基吲哚-3-基）-4-吲哚-3-基马来酰亚胺与DDQ / PPTS的氧化闭环反应，该环仅提供所需的阿曲霉素衍生物。尝试从3-（4-羟基吲哚基）-4-（2-氧代吲哚基）马来酰亚胺前体获得阿曲霉素系统不太成功，并且导致螺二氢吲哚化合物的氧化形成。 粘菌类生物碱-氧化环化-oxocin环形成-阿曲霉素
• Total synthesis of arcyroxocin A
  作者：Guido Mayer、Gregor Wille、Wolfgang Steglich

  DOI：10.1016/0040-4039(96)00864-7

  日期：1996.6

  The slime mould alkaloid arcyroxocin A (1) was synthesized by an acid catalyzed oxidative cyclization of the bisindolylmaleimide derivative 7.

  通过酸催化的双吲哚基马来酰亚胺衍生物7合成了煤泥霉菌生物碱阿曲霉素A（1）。
• Total syntheses of the slime mold alkaloid arcyriacyanin A
  作者：Michael Brenner、Guido Mayer、Andreas Terpin、Wolfgang Steglich

  DOI：10.1002/chem.19970030112

  日期：1997.1

  AbstractArcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4′‐biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4‐(triflyloxy)arcyriarubin 8 to N‐methylarcyriacyanin A (2). Thirdly, compound 2 was obtained by a domino Heck reaction between 3‐bromo‐4‐[1‐(tert‐butoxycarbonyl)indol‐3‐yl]‐1‐methylmaleimide (9) and 4‐bromoindole (10). The N‐methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.