3-acetyl-2-methyl-1-(phenylsulfonyl)indole | 113685-33-9

• 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: 3-acetyl-2-methyl-1-(phenylsulfonyl)indole
• 英文别名: 1-phenylsulfonyl-2-methyl-3-acetylindole；1-phenylsulfonyl-3-acetyl-2-methylindole；3-acetyl-2-methyl-1-phenylsulfonylindole；1-Phenylsulfonyl-2-methyl-3-acetylindol；1H-Indole, 3-acetyl-2-methyl-1-(phenylsulfonyl)-；1-[1-(benzenesulfonyl)-2-methylindol-3-yl]ethanone
• CAS: 113685-33-9
• 化学式: C₁₇H₁₅NO₃S
• 分子量: 313.377
• InChiKey: YYVXMNOFNMFPMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  519.6±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：

  3-acetyl-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92%的产率得到3-acetyl-2-(bromomethyl)-1-(phenylsulfonyl)indole
  参考文献：
  名称：

  Calothrixins B及其脱氧类似物的合成与生物学评价

  摘要：

  合成了一系列在“ E”环上带有取代基的邻氨基吡啶B（2）类似物及其缺少醌单元的脱氧喹咔唑。calothrixins的细胞毒性1，2，和15B - p和quinocarbazole类似物针对9个癌细胞系进行了研究。喹咔唑21a和25a抑制人拓扑异构酶II的催化活性。质粒DNA calothrixins裂解能力1，2，和15B - p确定的化合物15H导致DNA裂解的效果与calothrixin A（1）相当。Calothrixin A（1），3-fluorocalothrixin 15h和4- fluoroquino咔唑21b诱导了广泛的DNA损伤，随后凋亡的细胞死亡。光谱和质粒解旋研究证明了喹咔唑结合的插入模式。我们确定了两种有前途的候选药物，即在动物模型中具有低毒性的3-氟calothrixin B 15h及其脱氧衍生物4-氟喹咔唑21b对GI 50为1 nM的NCI-H460细胞系具有有效的细胞毒性。

  DOI：

  10.1021/acs.jmedchem.7b01797
• 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 18.25h， 生成 3-acetyl-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

• Diels-Alder Reactions of (1H-Indol-3-yl)-enacetamides and -endiacetamides: A Selective Access to Acetylamino-Functionalized [b]Annelated Indoles and Carbazoles
  作者：Ulf Pindur、Christian Otto、Michel Molinier、Werner Massa

  DOI：10.1002/hlca.19910740406

  日期：1991.6.19

  Diels-Alder reactions of the (1H-indol-3-yl)-enacetamides and -endiacetamides 1a–d with some carbodieno-philes and 4-phenyl-3H-1,2,4-triazole-3,5(4H)-dione give rise to the novel amino-functionalized carbazole; 4–6 and 8 (Scheme 3). Ethenetetracarbonitrile reacts with 1b to furnish the Michael-type adduct 7 (Scheme 3). Structural aspects of the starting materials 1, which exhibit above all 3-vinyl-1H-indole

  狄尔斯-阿尔德的（1反应ħ -吲哚-3-基）-enacetamides和-endiacetamides 1A - d与一些carbodieno-philes和4-苯基-3- ħ -1,2,4-三唑-3,5-（4- H）-二酮产生新的氨基官能化咔唑；4 – 6和8（方案3）。与Ethenetetracarbonitrile发生反应1B，得到的迈克尔型加成物7（流程3）。原材料1的结构方面，首先表现出3-乙烯基-1 H关于Diels - Alder过程的预测，讨论了对吲哚的反应性。
• Synthesis of N-protected indolaldehydes using modified Hass procedure
  作者：Ramalingam Balamurugan、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2007.08.035

  日期：2007.11

  A detailed study on oxidation of N-protected bromomethylindoles into the respective aldehydes was carried out. Using a modified Hass procedure, synthesis of aryl-/hetero-aryl aldehydes in particular indolaldehydes is achieved in reasonable yields. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of 3-Indolylpyrroles via Base-Mediated Cycloaddition of TOSMIC with Activated Indole-2/3-vinylenes
  作者：Ramalingam Balamurugan、Radhakrishnan Sureshbabu、Ganesan Gobi Rajeshwaran、Arasambattu K. Mohanakrishnan

  DOI：10.1080/00397910802406703

  日期：2009.1.13

  A synthesis of various types of 3-indolylpyrroles is reported involving a base-mediated 1,3-dipolar cycloaddition of TOSMIC with activated indole-2-3-vinylenes.
• Unusual Acetylation of 2-Methyl-1-phenylsulfonylindole
  作者：Jean-Yves Mérour、Béatrice Malapel、Eric Desarbre

  DOI：10.1080/00397919608004636

  日期：1996.9

  Acetylation of 2-methyl-1-phenylsulfonylindole with an excess of aluminium chloride and acetic anhydride afforded exclusively 6-acetyl-3-chloro-2-methylindole and 6-acetyl-3-chloro-2-methyl-1-phenylsulfonylindole.
• Synthesis of substituted carbazoles via electrocyclization of in situ generated enamines from 1-phenylsulfonyl-2/(3)-methyl-3/(2)-vinylindoles and DMF·DMA/DMA·DMA
  作者：Radhakrishnan Sureshbabu、Ramalingam Balamurugan、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.tet.2009.03.010

  日期：2009.5

  Interaction of 2/(3)-methyl-3/(2)-vinylindoles and DMF center dot DMA/DMA center dot DMA at 110 degrees C led to the in situ generation of enamines, which on concurrent electrocyclization followed by subsequent aromatization afforded substituted carbazoles. (C) 2009 Elsevier Ltd. All rights reserved.