(3-methyl-1-(phenylsulfonyl)-1H-indol-2-yl)(phenyl)methanone | 77507-53-0

• 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: (3-methyl-1-(phenylsulfonyl)-1H-indol-2-yl)(phenyl)methanone
• 英文别名: (1-phenylsulfonyl-3-methyl-1H-indol-2-yl)(phenyl)methanone；2-benzoyl-3-methyl-1-(phenylsulfonyl)indole；Phenyl(3-methyl-1-phenylsulfonyl-1H-indol-2-yl)methanone；[1-(benzenesulfonyl)-3-methylindol-2-yl]-phenylmethanone
• CAS: 77507-53-0
• 化学式: C₂₂H₁₇NO₃S
• 分子量: 375.448
• InChiKey: PIHDDBQGTOHRRS-UHFFFAOYSA-N

物化性质

• 沸点：
  566.4±42.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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-methyl-1-(phenylsulfonyl)-1H-indol-2-yl)(phenyl)methanone 在 aluminum oxide 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 18-冠醚-6 、 potassium formate 作用下， 以 四氯化碳 为溶剂， 反应 55.5h， 生成 2-benzoyl-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
• 作为产物：
  描述：

  N-(苯基磺酰基)-3-甲基吲哚 在 manganese(IV) oxide 、 仲丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 生成 (3-methyl-1-(phenylsulfonyl)-1H-indol-2-yl)(phenyl)methanone
  参考文献：
  名称：

  A DIRECT LITHIATION ROUTE TO 2-ACYL-1-(PHENYLSULFONYL)INDOLES

  摘要：

  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).

  DOI：

  10.1081/scc-120004854

文献信息

• Construction of pyrrole- and indole-fused CF3-piperazine derivatives
  作者：Yu-Ting Tian、Yu-Wei Zong、Jing Nie、Fa-Guang Zhang、Jun-An Ma

  DOI：10.1016/j.jfluchem.2019.109361

  日期：2019.10

  yields with excellent chemoselectivities via a Pictet-Spengler reaction under mild and operationally simple conditions. The synthetic utility of this protocol was further extended by the facile preparation of indole-fused CF3-1,4-diazocane and enantioenriched CF3-piperazines via a vinylogous Pictet-Spengler reaction and an asymmetric Pictet-Spengler reaction, respectively.

  在温和且操作简单的条件下，通过Pictet-Spengler反应以中等至良好的产率和优异的化学选择性构建了一系列吡咯和吲哚稠合的三氟甲基官能化哌嗪衍生物。通过分别通过乙烯基的Pictet-Spengler反应和不对称的Pictet-Spengler反应，容易地制备吲哚稠合的CF 3 -1，4-重氮烷和对映体富集的CF 3-哌嗪，进一步扩展了该方案的合成用途。
• One-Pot Synthesis of 1-Phenylsulfonyl-2-aroylindoles
  作者：Vasudevan Dhayalan、Ganapathy Panchapakesan、Arasambattu K. Mohanakrishnan

  DOI：10.1080/00397911.2010.525333

  日期：2012.2.1

  Interaction of phenylsulfonyl-2-aminobenzaldehyde with 2-bromo-1-phenylethanones in the presence of K2CO3 followed by acid-catalyzed dehydration led to the formation of 1-phenylsulfonyl-2-aroylindoles.
• New synthesis of the antitumor 6H-pyrido[4,3-b]carbazole alkaloid ellipticine
  作者：Shinzo Kano、Eiichi Sugino、Shiroshi Shibuya、Satoshi Hibino

  DOI：10.1021/jo00327a031

  日期：1981.7
• 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.
• 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).