3-acetyl-6-methoxy-N-(toluenesulfonyl)indole | 265111-02-2

• 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-6-methoxy-N-(toluenesulfonyl)indole
• 英文别名: 1-[6-Methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]ethanone；1-[6-methoxy-1-(4-methylphenyl)sulfonylindol-3-yl]ethanone
• CAS: 265111-02-2
• 化学式: C₁₈H₁₇NO₄S
• 分子量: 343.403
• InChiKey: ZOZUJPGTWSMFAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.37
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-acetyl-6-methoxy-N-(toluenesulfonyl)indole 在 silver hexafluoroantimonate 、 正丁基锂 、 (S)-DTBM-segphos(AuCl)₂ 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 15.88h， 生成
  参考文献：
  名称：

  Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[b]indoles

  摘要：

  A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These: studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.

  DOI：

  10.1021/jacs.5b00613
• 作为产物：
  描述：

  6-甲氧基吲哚-3-甲醛 在 4-二甲氨基吡啶 、 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 3-acetyl-6-methoxy-N-(toluenesulfonyl)indole
  参考文献：
  名称：

  Gold(I)-Catalyzed Dearomative Rautenstrauch Rearrangement: Enantioselective Access to Cyclopenta[b]indoles

  摘要：

  A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These: studies show vast difference in enantioselectivity in the reactions of propargyl acetates and propargyl acetals in the chiral ligand-controlled Rautenstrauch reaction.

  DOI：

  10.1021/jacs.5b00613

文献信息

• A radical addition and cyclization relay promoted by Mn(OAc)3⋅2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study
  作者：Meng-Meng Xu、Lu-Yao Kou、Xiao-Guang Bao、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1016/j.cclet.2021.02.001

  日期：2021.6

  Novel and efficient Mn(OAc)3⋅2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

  新型高效的 Mn(OAc) 3 ⋅2H 2 O 促进了 3-吲哚甲醇和亚磷酸酯的自由基加成-[4 + 1] 环化中继，以中等至良好的产率提供了 1,2-氧杂磷并吲哚衍生物。基于实验和计算研究，提出了一种涉及自由基加成和分子内环化级联的机制。
• Syntheses and cytotoxicity evaluation of bis(indolyl)thiazole, bis(indolyl)pyrazinone and bis(indolyl)pyrazine: analogues of cytotoxic marine bis(indole) alkaloid
  作者：Biao Jiang、Xiao-Hui Gu

  DOI：10.1016/s0968-0896(99)00290-4

  日期：2000.2

  2,4-Bis(3'-indolyl)thiazoles, 3,5-bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis(3'-indolyl)pyrazine were synthesized and evaluated for cytotoxic activity against diverse human cancer cell lines by the National Cancer Institute. These compounds demonstrated significant inhibitory effects in the growth of a range of cancer cell lines. 2,4-Bis(3'-indolyl)thiazole displayed selective cytotoxicity against certain leukemia cell lines with GI(50) values in the low micromolar range while the substituted derivatives showed a broad spectrum of cytotoxic activity. 3,5-Bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis[3'-(N-methyl-indolyl)]pyrazine possessed strong inhibitory activity against a wide range of human tumor cell lines. The mechanism of action remained unknown. The results suggested that 2,4-bis(3'-indolyl)thiazoles, 3,5-bis(3'-indolyl)-2(1H)pyrazinone and 3,6-bis[3'-(N-methyl-indolyl)] pyrazine offer potential as lead compounds for the discovery of anticancer agents. (C) 2000 Elsevier Science Ltd. All rights reserved.