2-ethyl-1-tosyl-1H-indole | 1192805-45-0

• 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-ethyl-1-tosyl-1H-indole
• 英文别名: 2-Ethyl-1-(4-methylphenyl)sulfonylindole
• CAS: 1192805-45-0
• 化学式: C₁₇H₁₇NO₂S
• 分子量: 299.393
• InChiKey: IJTZGZSNYLBEQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethyl-1-tosyl-1H-indole 在 正丁基锂 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 23.83h， 生成 benzyl 2-(2-ethyl-1H-indol-3-yl)acetate
  参考文献：
  名称：

  Design and Synthesis of Indomethacin Analogues That Inhibit P-Glycoprotein and/or Multidrug Resistant Protein without Cox Inhibitory Activity

  摘要：

  We designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug resistance indicated that NSAIDS modulation of multidrug-resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities.

  DOI：

  10.1021/jm301084z
• 作为产物：
  描述：

  N-p-toluenesulfonyl-2-(2-ethylethynyl)aniline 在 caesium carbonate 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以93.5%的产率得到2-ethyl-1-tosyl-1H-indole
  参考文献：
  名称：

  一种N-对甲苯磺酰基-2-取代吲哚类化合物的催化合成方法

  摘要：

  本发明公开的N‑对甲苯磺酰基‑2‑取代吲哚类化合物的催化合成方法，包括：常温常压下，将N‑对甲苯磺酰基‑2‑炔基取代的苯胺溶于乙腈中，N‑对甲苯磺酰基‑2‑炔基取代的苯胺与乙腈的摩尔体积比为1:1mmol/mL，得到N‑对甲苯磺酰基‑2‑炔基取代的苯胺的乙腈溶液；再向乙腈溶液中加入氯化亚铜和碳酸铯，氯化亚铜和碳酸铯的摩尔用量分别为N‑对甲苯磺酰基‑2‑炔基取代的苯胺摩尔用量的5%；之后，室温搅拌6小时，反应生成N‑对甲苯磺酰基‑2‑取代吲哚类化合物。该合成方法的成本低、收率高，其制备1g的N‑对甲苯磺酰基‑2‑取代吲哚类化合物所需催化剂的成本较现有以铑催化剂为催化剂的合成方法降低3个数量级，收率提高至89.1～97.0%。

  公开号：

  CN109651228B

文献信息

• Synthesis of Functionalized Indoles via Palladium-Catalyzed Aerobic Cycloisomerization of <i>o</i>-Allylanilines Using Organic Redox Cocatalyst
  作者：Xiao-Shan Ning、Mei-Mei Wang、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.joc.8b01999

  日期：2018.11.2

  A scalable and practical synthesis of functionalized indoles via Pd-tBuONO cocatalyzed aerobic cycloisomerization of o-allylanilines is reported. Using molecular oxygen as a terminal oxidant, a series of substituted indoles were prepared in moderate to good yields. The avoidance of hazardous oxidants, heavy-metal cocatalysts, and high boiling point solvents such as DMF and DMSO enables this method

  报道了通过Pd- t BuONO共催化邻烯丙基苯胺的好氧环异构化可规模化和实用地合成官能化的吲哚。使用分子氧作为末端氧化剂，以中等至良好的产率制备了一系列取代的吲哚。避免使用有害的氧化剂，重金属助催化剂和高沸点溶剂（例如DMF和DMSO），可使该方法应用于药物合成。吲哚美辛的实用克级合成证明了其应用潜力。
• Aromatic Enamide/Ene Metathesis toward Substituted Indoles and Its Application to the Synthesis of Indomethacins
  作者：Yayoi Kasaya、Kosuke Hoshi、Yukiyoshi Terada、Atsushi Nishida、Satoshi Shuto、Mitsuhiro Arisawa

  DOI：10.1002/ejoc.200900520

  日期：2009.9

  A steric and electronic effect on enamide/ene metathesis, a novel preparation of 2-substituted indoles and 3-substituted indoles using enamide-ene metathesis as a key reaction, and its application to the synthesis of indomethacin are described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  描述了烯酰胺/烯复分解的空间和电子效应，使用烯酰胺 - 烯复分解作为关键反应制备 2-取代吲哚和 3-取代吲哚的新方法，及其在吲哚美辛合成中的应用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Tandem Phospha‐Michael Addition/ <i>N</i> ‐Acylation/ Intramolecular Wittig Reaction of aza‐ <i>o</i> ‐Quinone Methides: Approaches to 2,3‐Disubstituted Indoles
  作者：Ting‐Bi Hua、Fei Chao、Long Wang、Chen‐Yang Yan、Cong Xiao、Qing‐Qing Yang、Wen‐Jing Xiao

  DOI：10.1002/adsc.202000343

  日期：2020.7.16

  A tandem phospha‐Michael addition/N‐acylation/intramolecular Wittig reaction of in situ formed aza‐o‐QMs is disclosed. This approach features high functional group tolerance and provides a convenient and practical access to biologically significant indole derivatives (37 examples, up to 91% yield) under mild reaction conditions.

  一种串联磷迈克尔加成/ Ñ酰化分子内形成的原位Wittig反应氮杂/ ö -QMs中公开。该方法具有高度的官能团耐受性，在温和的反应条件下，可方便实用地获得生物学上重要的吲哚衍生物（37个实例，产率高达91％）。
• A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of <i>N</i>-Tosylaziridines Followed by Copper Powder-Mediated C–N Cyclization/Aromatization
  作者：Masthanvali Sayyad、Yerramsetti Nanaji、Manas K. Ghorai

  DOI：10.1021/acs.joc.5b02251

  日期：2015.12.18

  A simple strategy for the syntheses of 2-alkyl indoles via regioselective ring-opening of 2-(2-haloaryl)-3-alkyl-N-tosylaziridines with thiophenol, followed by copper powder-mediated intramolecular C-N cyclization and subsequent aromatization by the elimination of thiophenol, with good yields is described. Utilizing this protocol, 2-carboxyindole has been synthesized easily.
• Indomethacin Analogues that Enhance Doxorubicin Cytotoxicity in Multidrug Resistant Cells without Cox Inhibitory Activity
  作者：Mitsuhiro Arisawa、Yayoi Kasaya、Tohru Obata、Takuma Sasaki、Mika Ito、Hiroshi Abe、Yoshihiro Ito、Akihito Yamano、Satoshi Shuto

  DOI：10.1021/ml100292y

  日期：2011.5.12

  Conformationally restricted indomethacin analogues were designed and prepared from the corresponding 2-substituted indoles, which were synthesized by a one-pot isomerization/enamide-ene metathesis as the key reaction. Conformational analysis by calculations, NMR studies, and X-ray crystallography suggested that these analogues were conformationally restricted in the s-cis or the s-trans form due to the 2-substituent as expected. Their biological activities on cyclooxygenase-1 (COX-1) inhibition, cyclooxygenase-2 (COX-2) inhibition, and modulation of MRP-1-mediated multidrug resistance (MDR) are described. Some of these indomethacin analogues enhanced doxorubicin cytotoxicity, although they do not have any COX inhibitory activity, which suggests that the MDR-modulating effect of an NSAID can be unassociated with its COX-inhibitory activity. This may be an entry into the combination chemotherapy of doxorubicin with a MDR modulator.