N-phenyl-1,4-epoxy-1-methyl-4-phenyl-1,2,3,4-tetrahydro-5-(phenylsulfonyl)-2,3-carbazoledicarboximide | 143774-77-0

• 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: N-phenyl-1,4-epoxy-1-methyl-4-phenyl-1,2,3,4-tetrahydro-5-(phenylsulfonyl)-2,3-carbazoledicarboximide
• 英文别名: (1S,11S,12R,16S)-9-(benzenesulfonyl)-1-methyl-11,14-diphenyl-17-oxa-9,14-diazapentacyclo[9.5.1.02,10.03,8.012,16]heptadeca-2(10),3,5,7-tetraene-13,15-dione
• CAS: 143774-77-0；143839-27-4
• 化学式: C₃₃H₂₄N₂O₅S
• 分子量: 560.63
• InChiKey: SRUODGXDGVMFAR-LNXLNJASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  41
• 可旋转键数：
  4
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-ethyl-2-(α-hydroxyphenylmethyl)-1-(phenylsulfonyl)indole 在 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 碳酸氢钠 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 苯 为溶剂， 反应 79.0h， 生成 N-phenyl-1,4-epoxy-1-methyl-4-phenyl-1,2,3,4-tetrahydro-5-(phenylsulfonyl)-2,3-carbazoledicarboximide
  参考文献：
  名称：

  Syntheses and Diels-Alder cycloaddition reactions of 4H-furo[3,4-b]indoles. A regiospecific Diels-Alder synthesis of ellipticine

  摘要：

  Seven examples of the novel 4H-furo[3,4-b]indole ring system (3-9)-a stable, synthetic analogue of indole-2,3-quinodimethane-have been synthesized in 6-8 steps from simple indoles in overall yields of 21-28%. These 4H-furo[3,4-b]indoles undergo Diels-Alder reactions with several dienophiles (dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne), including ethyl acrylate, which reacts regiospecifically with furoindole 4 to afford a single carbazole ester (59). This result, predicted by molecular orbital calculations, was used to design and execute a regiospecific Diels-Alder synthesis of the antitumor alkaloid ellipticine (63). Thus, the trimethylsilyl triflate-induced reaction between furoindole 4 and dihydropyridone 68b is greater-than-or-equal-to 99% regioselective and affords lactam 70b in 89% yield. Further manipulation gives ellipticine (63) with no detectable (<1%) isoellipticine (64) in the crude product.

  DOI：

  10.1021/jo00048a021

文献信息

• Syntheses and Diels-Alder cycloaddition reactions of 4H-furo[3,4-b]indoles. A regiospecific Diels-Alder synthesis of ellipticine
  作者：Gordon W. Gribble、Daniel J. Keavy、Deborah A. Davis、Mark G. Saulnier、Benjamin Pelcman、Timothy C. Barden、Mukund P. Sibi、Erik R. Olson、Joseph J. BelBruno

  DOI：10.1021/jo00048a021

  日期：1992.10

  Seven examples of the novel 4H-furo[3,4-b]indole ring system (3-9)-a stable, synthetic analogue of indole-2,3-quinodimethane-have been synthesized in 6-8 steps from simple indoles in overall yields of 21-28%. These 4H-furo[3,4-b]indoles undergo Diels-Alder reactions with several dienophiles (dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne), including ethyl acrylate, which reacts regiospecifically with furoindole 4 to afford a single carbazole ester (59). This result, predicted by molecular orbital calculations, was used to design and execute a regiospecific Diels-Alder synthesis of the antitumor alkaloid ellipticine (63). Thus, the trimethylsilyl triflate-induced reaction between furoindole 4 and dihydropyridone 68b is greater-than-or-equal-to 99% regioselective and affords lactam 70b in 89% yield. Further manipulation gives ellipticine (63) with no detectable (<1%) isoellipticine (64) in the crude product.