N,N-dimethyl-2-((4-nitrophenyl)ethynyl)aniline | 62167-05-9

• 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: N,N-dimethyl-2-((4-nitrophenyl)ethynyl)aniline
• 英文别名: N,N-dimethyl-2-[2-(4-nitrophenyl)ethynyl]aniline
• CAS: 62167-05-9
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: YPXZKZXPSIEGJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-((4-nitrophenyl)ethynyl)aniline 在 叔丁基过氧化氢 、 copper(l) iodide 、 lithium chloride 、 palladium(II) bromide 作用下， 以 癸烷 、 甲苯 为溶剂， 以73%的产率得到(1-methyl-1H-indol-3-yl) (4-nitrophenyl)methanone
  参考文献：
  名称：

  钯-铜-共催化的分子内氧化偶联：合成3-acylindoles的有效和原子经济的策略。

  摘要：

  展示了一种新的高效催化方法，可在Pd-Cu共催化的氧化条件下合成3-acylindoles。叔丁基氢过氧化物（TBHP）在该方法中不仅充当氧化剂，而且充当氧气源。该方法允许从容易获得的原料中快速且原子经济地组装3-acylindoles，并能耐受各种官能团。

  DOI：

  10.1039/c2cc37805a
• 作为产物：
  描述：

  1-乙炔基-4-硝基苯 、 邻碘-N,N-二甲基苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 生成 N,N-dimethyl-2-((4-nitrophenyl)ethynyl)aniline
  参考文献：
  名称：

  Synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl-N,N-dialkylanilines

  摘要：

  从2-炔基-N,N-二烷基苯胺和磺酰肼合物中合成N-烷基-3-磺酰基吲哚和N-烷基-3-硫基吲哚的分歧合成已被描述。

  DOI：

  10.1039/c7ob00366h

文献信息

• Iron-Facilitated Iodine-Mediated Electrophilic Annulation of N,N-Dimethyl-2-alkynylanilines with Disulfides or Diselenides
  作者：Hui-Ai Du、Ri-Yuan Tang、Chen-Liang Deng、Yan Liu、Jin-Heng Li、Xing-Guo Zhang

  DOI：10.1002/adsc.201100349

  日期：2011.10

  synthesis of N-methyl-3-chalcogeno-indoles has been developed via iodine-mediated electrophilic annulation reactions of 2-alkynylaniline derivatives with disulfides or diselenides. In the presence of iodine and iron, a variety of 2-alkynylanilines selectively underwent the electrophilic annulation with numerous disulfides or diselenides leading to the corresponding 3-sulfenylindoles and 3-selenenylindoles

  通过碘介导的2-炔基苯胺衍生物与二硫化物或二硒化物的亲电子环化反应，已经开发出N-甲基-3-硫属元素吲哚的有效合成方法。在碘和铁的存在下，各种2-炔基苯胺与众多的二硫化物或二硒化物选择性地进行亲电子环化反应，从而以中等至极好的收率得到相应的3-亚磺基吲哚和3-亚硒基吲哚。值得注意的是，铁可以促进反应。
• Palladium-catalyzed synthesis of 2,3-disubstituted indoles <i>via</i> arylation of <i>ortho</i>-alkynylanilines with arylsiloxanes
  作者：Yang-Ting Hsia、Yu-Lin Lu、Rekha Bai、Satpal Singh Badsara、Chin-Fa Lee

  DOI：10.1039/d3ob00961k

  日期：——

  study, we report the electrophilic cyclization of N,N-dimethyl-o-alkynylanilines with arylsiloxanes in the presence of [Pd(OAc)2] and Ag2O catalytic system, which leads to the efficient synthesis of indoles, similar to the one that is obtained through Larock indole synthesis. A range of aryl(trimethoxy)silanes with EDGs and EWGs were successfully utilized for the synthesis of a diverse variety of substituted

  在本研究中，我们报道了在[Pd(OAc) 2 ]和Ag 2 O催化体系存在下，N , N-二甲基邻炔基苯胺与芳基硅氧烷发生亲电环化，从而有效合成吲哚，类似于通过 Larock 吲哚合成获得的一种。一系列具有 EDG 和 EWG 的芳基（三甲氧基）硅烷已成功用于通过C-Si 键断裂合成各种取代吲哚。该方案具有良好的官能团耐受性和广泛的底物范围，能够以 26-88% 的产率提供 2,3-二芳基-N-甲基吲哚。
• Palladium(II)-Catalyzed Tandem Cyclization/C–H Functionalization of Alkynes for the Synthesis of Functionalized Indoles
  作者：Xiao-Feng Xia、Ning Wang、Lu−Lu Zhang、Xian-Rong Song、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/jo301741j

  日期：2012.10.19

  A palladium-catalyzed tandem cyclization/C-H functionalization of two alkynes was accomplished to construct a series of polycyclic functionalized indoles. A range of internal alkynes bearing synthetically useful functional groups were tolerated. A good regioselectivity was observed when alkyl-substituted alkynes were introduced into the reaction system, and a single product was obtained. Molecular oxygen was used as the terminal oxidant in the approach, rendering the reaction more sustainable.
• A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp³ C–H Bond Activation Followed by C–C and C–O Bond Formation
  作者：Anupal Gogoi、Srimanta Guin、Saroj Kumar Rout、Bhisma K. Patel

  DOI：10.1021/ol400692b

  日期：2013.4.19

  An efficient Cu(I)-catalyzed synthesis of 3-aroylindoles has been achieved from o-alkynylated N,N-dimethylamines via a sp(3) C-H bond activation a to the nitrogen atom followed by an intramolecular nucleophilic attack with the alkyne using an aqueous solution of tert-butyl hydroperoxide (TBHP) as the oxidant. In this tandem catalytic synthesis of 3-aroylindoles both C-C and C-O bonds are installed at the expense of two sp(3) C-H bond cleavages.
• Synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles by cascade annulation of 2-alkynyl-N,N-dialkylanilines
  作者：Jatuporn Meesin、Manat Pohmakotr、Vichai Reutrakul、Darunee Soorukram、Pawaret Leowanawat、Chutima Kuhakarn

  DOI：10.1039/c7ob00366h

  日期：——

  Divergent synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles from 2-alkynyl-N,N-dialkylanilines and sulfonyl hydrazides has been described.

  从2-炔基-N,N-二烷基苯胺和磺酰肼合物中合成N-烷基-3-磺酰基吲哚和N-烷基-3-硫基吲哚的分歧合成已被描述。