4-methoxy-N,N-di(prop-2-ynyl)benzenamine | 22774-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxy-N,N-di(prop-2-ynyl)benzenamine
• 英文别名: 4-methoxy-N,N-di(prop-2-yn-1-yl)aniline；(4-methoxyphenyl)diprop-2-ynylamine；N,N-Dipropargyl-p-anisidin；4-methoxy-N,N-bis(prop-2-ynyl)aniline
• CAS: 22774-34-1
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: ZZXPCOAQQIBQIX-UHFFFAOYSA-N

物化性质

• 熔点：
  52-53 °C(Solvent: Methanol)
• 沸点：
  317.4±37.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methoxy-N,N-di(prop-2-ynyl)benzenamine 在 氧气 作用下， 以 丙酮 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以73%的产率得到
  参考文献：
  名称：

  Visible-light-induced oxidative formylation of N-alkyl-N-(prop-2-yn-1-yl)anilines with molecular oxygen in the absence of an external photosensitizer

  摘要：

  可见光诱导的氧化甲酰化反应，使用分子氧在温和的反应条件下，无需外部光敏剂，对N-烷基-N-(丙-2-炔-1-基)苯胺进行了研究。

  DOI：

  10.1039/c7cc03693k
• 作为产物：
  描述：

  炔丙基苯磺酸 、 甲氧苯胺 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 4-methoxy-N,N-di(prop-2-ynyl)benzenamine
  参考文献：
  名称：

  Vizgert,R.V. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 914 - 919

  摘要：

  DOI：

文献信息

• Highly selective N-Alkylation of amines promoted on silica: An efficient and recyclable surface
  作者：Basudeb Basu、Susmita Paul、Ashis K. Nanda

  DOI：10.1039/b905878h

  日期：——

  N-Alkylation of amines suffers from competing over alkylations. At the same time, use of strong base and other harsh conditions greatly limits providing a practical, generalized and selective procedure. Activated silica gel has been found to promote N-alkylations of amines. Here, we studied N-alkylation of amines with various types of alkyl halides, which finally constitute practical, highly selective and eco-friendly conditions for mono- or bis-alkylated amines at ambient temperature with recyclability of silica.

  胺类的N-烷基化面临竞争性过烷基化的问题。同时，强碱和其他苛刻条件的使用大大限制了提供实际、普遍和选择性的程序。研究发现活化硅胶能够促进胺类的N-烷基化。在此，我们研究了与各种烷基卤化物作用的胺类N-烷基化，最终构建了在环境温度下、具有可再生硅胶的单烷基或双烷基化胺的实用、高选择性和环保条件。
• Intermolecular and Intramolecular Pauson–Khand Reactions of Functionalized Allenes
  作者：Álvaro González-Gómez、Loreto Añorbe、Amalia Poblador、Gema Domínguez、Javier Pérez-Castells

  DOI：10.1002/ejoc.200701038

  日期：2008.3

  Pauson–Khand reactions of functionalized allenes with different alkynes give cyclopentenones with generally high regio- and stereoselectivities. The allenes react through their external double bonds, giving cyclopentenones with exocyclic double bond at their β positions and predominantly with E stereochemistry. Some intramolecular reactions with allenynes connected through aromatic rings are described

  具有不同炔烃的官能化丙二烯的 Pauson-Khand 反应产生具有通常高区域选择性和立体选择性的环戊烯酮。丙二烯通过它们的外部双键反应，得到在其 β 位置具有环外双键的环戊烯酮，主要是 E 立体化学。描述了通过芳环连接的丙炔的一些分子内反应。这些以中等至良好的产率得到相应的杂环。
• Direct and Selective N-Monoalkynylation and N-Monoalkenylation of Anilines with Alky(e)nyl Methanesulfonates Using Methylmagnesium Bromide as a Base
  作者：Yoshihiro Yoshida、Yoo Tanabe

  DOI：10.1055/s-1997-1225

  日期：1997.5

  Several anilines were directly N-monoalkynylated and N-monoalkenylated with alkynyl methanesulfonates and alkenyl methanesulfonates, respectively, using methylmagnesium bromide as a base in good yields with high selectivities.

  以甲基溴化镁为碱，分别用炔基甲烷磺酸盐和烯基甲烷磺酸盐直接对几种苯胺进行了 N-单炔基化和 N-单烯炔基化，收率高，选择性强。
• A highly efficient tandem [3 + 2] “click” cycloaddition/6-<i>exo</i>-cyclization strategy for the construction of triazole fused pyrazines
  作者：Biswajit Roy、Debashis Mondal、Joydev Hatai、Subhajit Bandyopadhyay

  DOI：10.1039/c4ra12489h

  日期：——

  The pharmaceutically important tetrahydro-[1,2,3]triazolopyrazine heterocyclic architecture has been synthesized via a concise tandem “click”/6-exo-dig cyclization strategy under mild conditions in mixed aqueous–organic media.

  具有药用价值的四氢-[1,2,3]三唑吡嗪杂环结构已通过在混合水-有机介质中，在温和条件下利用简洁的串联“点击”/6-外向环化策略合成。
• Synthesis of polyfunctional triethoxysilanes by ‘click silylation’
  作者：Gurjaspreet Singh、Satinderpal Singh Mangat、Jandeep Singh、Aanchal Arora、Ramesh K. Sharma

  DOI：10.1016/j.tetlet.2013.12.037

  日期：2014.1

  The copper-catalyzed 'click silylation' has been exploited for the chemical modification of gamma-azidopropyltriethoxysilane (AzPTES) with a wide range of terminal alkynes (la-lv) in a one-pot operation. The novel 1,2,3-triazole-triethoxysilane derivatives (2a-2v) were synthesized by this procedure and comprehensively characterized by IR spectra, H-1 and C-13 NMR, and HRMS studies. (C) 2013 Elsevier Ltd. All rights reserved.