2-propyl-1-tosyl-1H-indole | 1162682-08-7

• 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-propyl-1-tosyl-1H-indole
• 英文别名: 1-(4-Methylphenyl)sulfonyl-2-propylindole；1-(4-methylphenyl)sulfonyl-2-propylindole
• CAS: 1162682-08-7
• 化学式: C₁₈H₁₉NO₂S
• 分子量: 313.42
• InChiKey: NTHMEGBBFYAASD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-tosyl-2-(propylethynyl)aniline 在 C₄₀H₄₃N₄OScSi 作用下， 反应 3.0h， 以87%的产率得到2-propyl-1-tosyl-1H-indole
  参考文献：
  名称：

  不对称辅助串联催化：加氢胺化反应，然后由单个手性N，N，N'，N'-四齿吡啶基甲胺基配体进行不对称Friedel-Crafts反应

  摘要：

  随着人们对稀土元素的不对称催化的兴趣不断提高，手性配体无疑将成为催化剂中最有价值的单元。本文报道了在不对称辅助串联催化方案中使用多任务手性配体的概念的第一个证据，该方案先后结合了金属催化过程和有机催化过程。在该方案中，通过简单添加HCl，将新设计的第一个反应的稀土催化剂的手性配体转化为新型的手性有机催化剂，用于第二个转化。观察到串联序列中的一些对映体诱导-炔烃加氢胺化，然后进行对映选择性的Friedel-Crafts烷基化反应，证实了手性N，N，N'，N'-四齿配体及其吡啶基甲胺支架的重要性。

  DOI：

  10.1002/cctc.201600604

文献信息

• An efficient synthesis of indoles via a CuMgAl-LDH-catalyzed cyclization of 2-alkynylsulfonanilides
  作者：Sheng-Yan Zhang、Shan-Gang Sun、Yu-Shuang Guo、Xiao-Fan Lu、Dian-Shun Guo

  DOI：10.1016/j.tetlet.2018.09.009

  日期：2018.10

  A highly efficient method for the synthesis of indoles has been successfully developed via a CuMgAl-LDH-catalyzed intramolecular annulation reaction of 2-alkynylsulfonanilides. This CuMgAl-LDH catalyst features facile preparation, recovery, and reuse at least seven times without a marked loss in the catalytic activity, as well as the unique dual activation. Moreover, the crystal structures and Hirshfeld

  通过CuMgAl-LDH催化的2-炔基磺酰苯胺的分子内环化反应已成功开发了一种高效的吲哚合成方法。这种CuMgAl-LDH催化剂的特征是易于制备，回收和重复使用至少7次，而催化活性没有明显损失，并且具有独特的双重活化作用。此外，还介绍了典型的吲哚化合物的晶体结构和Hirshfeld表面分析。
• Selenium-Catalyzed Oxidative C(sp²)–H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles
  作者：Stefan Ortgies、Alexander Breder

  DOI：10.1021/acs.orglett.5b01156

  日期：2015.6.5

  A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp2)–H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily accessible ortho-vinyl anilines and vinylated aminopyridines, respectively. The procedure exploits the pronounced

  报道了一种使用N-氟苯磺酰亚胺作为末端氧化剂直接，分子内胺化C（sp 2）-H键的新的硒催化方案。该方法能够容易地形成分别衍生自容易获得的邻乙烯基苯胺和乙烯基化氨基吡啶的多种多样的功能化的吲哚和氮杂吲哚。该方法利用硒亲电试剂的显着的亲碳性来催化烯烃的活化，并导致高产率且具有出色的官能团耐受性的C（sp 2）–N键形成。
• 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.
• Palladium-free zinc-mediated hydroamination of alkynes: efficient synthesis of indoles from 2-akynylaniline derivatives
  作者：Kentaro Okuma、Jun-ichi Seto、Ken-ichi Sakaguchi、Saori Ozaki、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.1016/j.tetlet.2009.03.210

  日期：2009.6

  Reaction of 2-phenylethynyl N-tosylanilide prepared by Pd-free procedure with ZnBr(2) (3 equiv) in refluxing toluene gave N-tosyl-2-phenylindole in 93% yield. Treatment of 2-phenylethynylaniline with ZnBr(2) (1 equiv) in refluxing toluene resulted in the formation of 2-phenylindole in 91% yield. Catalytic ZnBr(2) (0.05 equiv) effectively reacted with 2-alkynylanilines to afford 2-substituted indoles in high yields. Thus, complete Pd-free zinc catalyzed hydroamination of 2-alkynylanilines was achieved. (C) 2009 Elsevier Ltd. All rights reserved.