5-methoxy-2-phenyl-1-tosyl-1H-indole | 910896-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-methoxy-2-phenyl-1-tosyl-1H-indole
• 英文别名: 5-Methoxy-1-(4-methylphenyl)sulfonyl-2-phenylindole
• CAS: 910896-38-7
• 化学式: C₂₂H₁₉NO₃S
• 分子量: 377.464
• InChiKey: RXDSCYNOQFXRNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2-iodo-4-methoxyphenyl)-4-methylbenzenesulfonamide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 [1,1'-二(二叔丁基膦)二茂铁]合二氯钯(II) 、 三乙胺 、 三苯基膦 、 四甲基胍 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 5-methoxy-2-phenyl-1-tosyl-1H-indole
  参考文献：
  名称：

  Tandem Sonogashira-Hagihara Coupling/Cycloisomerization Reactions of Ethynylboronic Acid MIDA Ester to Afford 2-Heterocyclic Boronic Acid MIDA Esters: A Concise Route to Benzofurans, Indoles, Furopyridines and Pyrrolopyridines

  摘要：

  A one-pot process that provides direct access to 2-heterocyclic MIDA (N-methyliminodiacetic acid) boronates has been developed. The reaction of 2-iodophenols or 2-iodoanilines with ethynylboronic acid MIDA ester readily afforded 2-substituted heterocyclic compounds. Amidine and phosphazene bases, especially TMG (1,1,3,3-tetramethylguanidine) assumed an important role in the tandem Sonogashira-Hagihara coupling/cycloisomerization reactions.

  DOI：

  10.3987/com-17-13723

文献信息

• Silver(I)-Mediated CH Amination of 2-Alkenylanilines: Unique Solvent-Dependent Migratory Aptitude
  作者：So Won Youn、Tae Yun Ko、Min Jung Jang、Su San Jang

  DOI：10.1002/adsc.201400759

  日期：2015.1.12

  A highly effective silver(I)‐mediated CH amination of 2‐alkenylanilines has been developed to afford a diverse range of substituted indoles. High functional group tolerance, broad substrate scope, simple/fast/high‐yielding reaction, and recovery/reuse of the inexpensive silver oxidant are noteworthy. Furthermore, an uncommon migratory process of β‐monosubstituted 2‐alkenylanilines with solvent‐dependence

  已开发出一种高效的银（I）介导的2-烯基苯胺的CH胺化反应，以提供各种取代的吲哚。值得注意的是，高官能团耐受性，广泛的底物范围，简单/快速/高产率的反应以及廉价的银氧化剂的回收/再利用。此外，还证明了具有溶剂依赖性的β-单取代2-烯基苯胺的不常见迁移过程。
• 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。
• DMSO/SOCl₂-mediated C(sp²)–H amination: switchable synthesis of 3-unsubstituted indole and 3-methylthioindole derivatives
  作者：Jingran Zhang、Xiaoxian Li、Xuemin Li、Haofeng Shi、Fengxia Sun、Yunfei Du

  DOI：10.1039/d0cc07453e

  日期：——

  The reaction of 2-alkenylanilines with SOCl2 in DMSO was found to selectively afford 3-unsubstituted indoles and 3-methylthioindoles. This switchable approach was found to be temperature-dependent: at room temperature, the reaction afforded 3-unsubstituted indoles through intramolecular cyclization and elimination; while at higher temperature, the reaction gave 3-methylthioindoles via further electrophilic

  发现2-烯基苯胺与SOCl 2在DMSO中的反应选择性地提供3-未取代的吲哚和3-甲基硫代吲哚。发现这种可转换的方法是温度依赖性的：在室温下，该反应通过分子内环化和消除得到3-未取代的吲哚；在较高温度下，反应通过进一步的亲电甲基硫醇化反应生成3-甲基硫吲哚。
• Nickel-Catalyzed Arylative Additions on 2-Alkynyl-<i>N</i> -Arylsulfonylanilides to Construct Functionalized Indoles
  作者：Christopher N. Voth、Gregory R. Dake

  DOI：10.1002/ejoc.201901835

  日期：2020.2.14

  The addition of aryl iodides to 2‐alkynyl‐N‐sulfonylanilides to form 2,3‐difunctionalized N‐arylsulfonylindoles can be catalyzed using a nickel catalyst ligated to a bis(cyclohexanyl)phosphinoferrocene. A variety of nickel complexes can be used as precatalysts including a complex derived from inexpensive NiCl2·6H2O. Electron‐rich aryl iodides are superior partners in this transformation.

  可以使用连接至双（环己基）膦基二茂铁的镍催化剂来催化将芳基碘化物添加到2-炔基-N-磺酰腈中以形成2,3-二官能化的N-芳基磺酰吲哚。多种镍络合物可用作预催化剂，包括衍生自廉价NiCl 2 · 6H 2 O的络合物。富电子芳基碘化物是该转化过程中的最佳伙伴。
• 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％）。