2-acetyl-3-(hydroxymethyl)-1-(phenylsulfonyl)indole | 143774-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-acetyl-3-(hydroxymethyl)-1-(phenylsulfonyl)indole
• 英文别名: 1-[1-(Benzenesulfonyl)-3-(hydroxymethyl)indol-2-yl]ethanone
• CAS: 143774-65-6
• 化学式: C₁₇H₁₅NO₄S
• 分子量: 329.376
• InChiKey: QNINDYNBSWXOQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-acetyl-3-(hydroxymethyl)-1-(phenylsulfonyl)indole 在 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以79%的产率得到3-methyl-4-(phenylsulfonyl)-4H-furo<3,4-b>indole
  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
• 作为产物：
  描述：

  N-(苯基磺酰基)-3-甲基吲哚 在 manganese(IV) oxide 、 aluminum oxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 18-冠醚-6 、 仲丁基锂 、 potassium formate 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 162.75h， 生成 2-acetyl-3-(hydroxymethyl)-1-(phenylsulfonyl)indole
  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

• Photodesulfonylation of indoles initiated by electron transfer from triethylamine
  作者：Xuechuan Hong、José M. Mejía-Oneto、Stefan France、Albert Padwa

  DOI：10.1016/j.tetlet.2006.01.152

  日期：2006.4

  N-Sulfonyl indoles can be easily deprotected by a photoinduced electron transfer reaction with triethylamine. By using an equivalent amount of n-Bu3SnH in the photolysis medium, it is possible to suppress the competitive photo-Fries like rearrangement by scavenging the phenylsulfonyl radical.

  N-磺酰基吲哚可以通过与三乙胺的光诱导电子转移反应而容易地脱保护。通过在光解介质中使用等量的n -Bu 3 SnH，可以通过清除苯基磺酰基自由基来抑制竞争性的光敏性，如重排。