2-pentyl-1-tosyl-1H-indole | 1162682-09-8

• 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-pentyl-1-tosyl-1H-indole
• 英文别名: 2-pentyl-N-tosylindole；2-pentyl-1-(4-methylbenzenesulfonyl)-1H-indole；1-(4-Methylphenyl)sulfonyl-2-pentylindole
• CAS: 1162682-09-8
• 化学式: C₂₀H₂₃NO₂S
• 分子量: 341.474
• InChiKey: MCDMUQVYJBNGIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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-(2-(hept-1-yn-1-yl)phenyl)-4-methylbenzenesulfonamide 在 zinc dibromide 作用下， 以 甲苯 为溶剂， 反应 32.0h， 以91%的产率得到2-pentyl-1-tosyl-1H-indole
  参考文献：
  名称：

  Palladium-free zinc-mediated hydroamination of alkynes: efficient synthesis of indoles from 2-akynylaniline derivatives

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.03.210

文献信息

• Copper-Mediated Cyclization−Halogenation and Cyclization−Cyanation Reactions of β-Hydroxyalkynes and <i>o</i>-Alkynylphenols and Anilines
  作者：Nalivela Kumara Swamy、Arife Yazici、Stephen G. Pyne

  DOI：10.1021/jo1005119

  日期：2010.5.21

  The CuX (X = I, Br, Cl, CN)-mediated cyclization−halogenation and cyclization−cyanation reactions of β-hydroxyalkynes and o-alkynylphenol and -aniline derivatives give rise to 3-halo- and 3-cyanofuro[3,2-b]pyrroles, 3-iodo-, 3-bromo-, and 3-cyanobenzofurans, and 3-cyanoindoles, respectively.

  CuX（X = I，Br，Cl，CN）介导的β-羟基炔烃与邻炔基苯酚和-苯胺衍生物的环化-卤化和环化-氰化反应生成3-卤代和3-氰基呋喃[3,2 - b ]吡咯，3-碘，3-溴-和3- cyanobenzofurans和3- cyanoindoles，分别。
• Synthesis of Benzofurans and Indoles from Terminal Alkynes and Iodoaromatics Catalyzed by Recyclable Palladium Nanoparticles Immobilized on Siliceous Mesocellular Foam
  作者：Alexandre Bruneau、Karl P. J. Gustafson、Ning Yuan、Cheuk-Wai Tai、Ingmar Persson、Xiaodong Zou、Jan-E. Bäckvall

  DOI：10.1002/chem.201702614

  日期：2017.9.18

  (Pd0‐AmP‐MCF), for the synthesis of heterocycles. Reaction of o‐iodophenols and protected o‐iodoanilines with acetylenes in the presence of a Pd nanocatalyst produced 2‐substituted benzofurans and indoles, respectively. In general, the catalytic protocol afforded the desired products in good to excellent yields under mild reaction conditions without the addition of ligands. Moreover, the structure

  在本文中，我们报告了一种多相催化剂的利用，该催化剂由硅质介孔泡沫（Pd 0 -AmP-MCF）上负载的Pd纳米颗粒组成，用于杂环的合成。的反应Ó -iodophenols和保护ö与乙炔-iodoanilines在Pd纳米催化剂的存在下生产2-取代的苯并呋喃并吲哚，分别。通常，在温和的反应条件下，无需添加配体，催化方案就能以令人满意的良好收率获得所需的产物。此外，通过扩展的X射线吸收精细结构光谱进一步阐明了所报道的Pd纳米催化剂的结构，并且证明了该催化剂可以多次循环使用，而活性没有明显损失。
• 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.