2-acetyl-3-methyl-1-(phenylsulfonyl)indole | 143774-63-4

• 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-methyl-1-(phenylsulfonyl)indole
• 英文别名: 1H-Indole, 2-acetyl-3-methyl-1-(phenylsulfonyl)-；1-[1-(benzenesulfonyl)-3-methylindol-2-yl]ethanone
• CAS: 143774-63-4
• 化学式: C₁₇H₁₅NO₃S
• 分子量: 313.377
• InChiKey: FZOJVCJGKMSWOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-acetyl-3-methyl-1-(phenylsulfonyl)indole 在 aluminum oxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 18-冠醚-6 、 三氟化硼乙醚 、 potassium formate 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 123.0h， 生成 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-苯磺酰基-3-(溴甲基)吲哚 在 polyphosphoric ester 、 Raney-Ni W₂ 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 10.33h， 生成 2-acetyl-3-methyl-1-(phenylsulfonyl)indole
  参考文献：
  名称：

  Mohanakrishnan, A. K.; Srinivasan, P. C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 8, p. 838 - 841

  摘要：

  DOI：

文献信息

• Cyclocondensation Reactions between 2-Acyl-3-indoleacetic Acid Derivatives and Phenylglycinol: Enantioselective Synthesis of 1-Substituted Tetrahydro-β-carboline Alkaloids
  作者：Mercedes Amat、Fabiana Subrizi、Viviane Elias、Núria Llor、Elies Molins、Joan Bosch

  DOI：10.1002/ejoc.201101718

  日期：2012.3

  Cyclocondensation reactions between a variety of 2-acyl-3-indoleacetic acid derivatives and (R)-phenylglycinol were studied. Successful results were obtained from N-alkyl keto acid derivatives. The resulting tetracyclic lactams provide straightforward access to enantiopure 1-substituted tetrahydro-β-carboline alkaloids.

  研究了各种 2-酰基-3-吲哚乙酸衍生物和 (R)-苯基甘氨醇之间的环缩合反应。N-烷基酮酸衍生物获得了成功的结果。由此产生的四环内酰胺提供了直接获取对映体纯 1-取代四氢-β-咔啉生物碱的途径。
• A DIRECT LITHIATION ROUTE TO 2-ACYL-1-(PHENYLSULFONYL)INDOLES
  作者：Jun Jiang、Gordon W. Gribble

  DOI：10.1081/scc-120004854

  日期：2002.1

  2-Acyl-1-(phenylsulfonyl)indoles (3, 7-9) are prepared in 75-84% yield from 1-(phenylsulfonyl)indoles (1, 5) in one operation by treatment of the latter with s-butyllithium followed by inverse quenching of the C-2 lithioindoles with carboxylic acid anhydrides (6).