4-bromo-N,N-dimethyl-2-[2-(4-methylphenyl)ethynyl]aniline | 1428872-76-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-bromo-N,N-dimethyl-2-[2-(4-methylphenyl)ethynyl]aniline
• CAS: 1428872-76-7
• 化学式: C₁₇H₁₆BrN
• 分子量: 314.225
• InChiKey: PLBLFHCGBJJHSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-N,N-dimethyl-2-[2-(4-methylphenyl)ethynyl]aniline 在 叔丁基过氧化氢 、 copper(I) bromide 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 以70%的产率得到(5-bromo-1-methyl-1H-indol-3-yl)(p-tolyl)methanone
  参考文献：
  名称：

  A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp³ C–H Bond Activation Followed by C–C and C–O Bond Formation

  摘要：

  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.

  DOI：

  10.1021/ol400692b
• 作为产物：
  描述：

  4-bromo-2-iodo-N,N-dimethylaniline 、 4-甲苯基乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 生成 4-bromo-N,N-dimethyl-2-[2-(4-methylphenyl)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

• 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。
• 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.