3-benzoyl-2-methyl-1-(phenylsulfonyl)indole | 143774-59-8

• 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-benzoyl-2-methyl-1-(phenylsulfonyl)indole
• 英文别名: 2-methyl-3-benzoylindole；(2-methyl-1-(phenylsulfonyl)-1H-indol-3-yl)(phenyl)methanone；(2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)(phenyl)methanone；[1-(benzenesulfonyl)-2-methylindol-3-yl]-phenylmethanone
• CAS: 143774-59-8
• 化学式: C₂₂H₁₇NO₃S
• 分子量: 375.448
• InChiKey: CDZUWMUKQWYZDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-2-methyl-1-(phenylsulfonyl)indole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以94%的产率得到3-benzoyl-2-(bromomethyl)-1-(phenylsulfonyl)indole
  参考文献：
  名称：

  SnCl 4介导的2-吲哚甲基新戊酸酯与芳烃和杂芳烃的多米诺反应合成环[ b ]稠合咔唑

  摘要：

  通过SnCl 4介导的一锅芳构化，环化和芳构化反应序列，从3-乙酰基/芳酰基-2-新戊酰氧基甲基吲哚开始开发了芳基和杂芳基环化的环[ b ]咔唑的直接合成方法。起始原料可通过Friedel-Crafts酰化，溴化和吡咯烷化反应从市售2-甲基吲哚轻松获得。值得注意的是，在本多米诺反应方案中，包括杂环系统在内的吸电子/给电子芳基单元具有良好的耐受性。此外，该方法可以扩展为通过2，5-双（2-新戊酰氧基甲基）吡咯的双环合成二苯并呋喃咔唑。

  DOI：

  10.1021/acs.joc.6b01646
• 作为产物：
  描述：

  N-苯磺酸吲哚 在 三氯化铝 、 lithium diisopropyl amide 作用下， 反应 18.0h， 生成 3-benzoyl-2-methyl-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

• An Improved Synthesis of Carbazoles<i>via</i>Domino Reaction of<i>N</i>-Protected-2-methylindoles with DMF-DMA/DMA-DMA
  作者：Radhakrishnan Sureshbabu、Arasambattu K. Mohanakrishnan

  DOI：10.1002/jhet.899

  日期：2012.7

  An efficient synthesis of carbazole analogs has been achieved via interaction of N‐protected‐2‐methylindoles with N,N‐dimethylformamide dimethylacetal as well as N,N‐dimethylacetamide dimethylacetal in the presence of pyrrolidine or 1,4‐diazabicyclo(2.2.2)octane (DABCO).
• PINDUR, ULF;PFEUFFER, LUDWIG, MONATSH. CHEM., 118,(1987) N 8-9, 1031-1038
  作者：PINDUR, ULF、PFEUFFER, LUDWIG

  DOI：——

  日期：——
• Synthesis of Cyclo[<i>b</i>]fused Carbazoles via SnCl₄-Mediated Domino Reaction of 2-Indolylmethylpivalates with Arenes and Heteroarenes
  作者：Velu Saravanan、Thiyagarajan Mageshwaran、Arasambattu K. Mohanakrishnan

  DOI：10.1021/acs.joc.6b01646

  日期：2016.9.16

  cyclo[b]carbazoles has been developed via SnCl4-mediated one-pot arylation, cyclization and aromatization reaction sequence from 3-acetyl/aroyl-2-pivaloyloxymethylindoles. The starting material is easily accessible from commercially available 2-methylindole via Friedel–Crafts acylation, bromination and pivaloylation. Remarkably, electron withdrawing/donating aroyl units including heterocyclic systems are well

  通过SnCl 4介导的一锅芳构化，环化和芳构化反应序列，从3-乙酰基/芳酰基-2-新戊酰氧基甲基吲哚开始开发了芳基和杂芳基环化的环[ b ]咔唑的直接合成方法。起始原料可通过Friedel-Crafts酰化，溴化和吡咯烷化反应从市售2-甲基吲哚轻松获得。值得注意的是，在本多米诺反应方案中，包括杂环系统在内的吸电子/给电子芳基单元具有良好的耐受性。此外，该方法可以扩展为通过2，5-双（2-新戊酰氧基甲基）吡咯的双环合成二苯并呋喃咔唑。
• 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.