N-methyl-3-(4'-methylphenyl)-2-propynylamine | 761000-55-9

• 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-methyl-3-(4'-methylphenyl)-2-propynylamine
• 英文别名: N-methyl-3-(p-tolyl)prop-2-yn-1-amine；N-methyl-3-(4-methylphenyl)prop-2-yn-1-amine
• CAS: 761000-55-9
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: GELGDRWWPYTATD-UHFFFAOYSA-N

物化性质

• 沸点：
  245.9±33.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-methyl-3-(4'-methylphenyl)-2-propynylamine 、 potassium N-cyano-2-fluorobenzamide 在 三甲基氯硅烷 作用下， 以 乙腈 为溶剂， 反应 1.17h， 以68%的产率得到2-fluoro-N-(N-methyl-N-(3-(p-tolyl)prop-2-yn-1-yl)carbamimidoyl)benzamide
  参考文献：
  名称：

  Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines

  摘要：

  A regioselective base-mediated cyclization of mono-N-acylpropargylguanidines is reported. A related Ag(I)-catalyzed hydroamination strategy was recently employed to yield N-3-Cbz-protected ene-guanidines, which found utility in the synthesis of naamidine A. Herein, we report the base-catalyzed hydroamination of mono-N-acylpropargylguanidines, which proceeds with the opposite regiochemistry to deliver isomerized N-2-acyl-2-aminoimidazoles with broad substrate scope, circumventing the problematic regiospecific acylation of free 2-aminoimidazoles.

  DOI：

  10.1021/acs.joc.7b00639
• 作为产物：
  描述：

  4-甲苯基乙炔 在 四(三苯基膦)钯 、 1,3-二甲基巴比妥酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 84.0h， 生成 N-methyl-3-(4'-methylphenyl)-2-propynylamine
  参考文献：
  名称：

  Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines

  摘要：

  A regioselective base-mediated cyclization of mono-N-acylpropargylguanidines is reported. A related Ag(I)-catalyzed hydroamination strategy was recently employed to yield N-3-Cbz-protected ene-guanidines, which found utility in the synthesis of naamidine A. Herein, we report the base-catalyzed hydroamination of mono-N-acylpropargylguanidines, which proceeds with the opposite regiochemistry to deliver isomerized N-2-acyl-2-aminoimidazoles with broad substrate scope, circumventing the problematic regiospecific acylation of free 2-aminoimidazoles.

  DOI：

  10.1021/acs.joc.7b00639

文献信息

• Efficient and Reusable Metal-Organic Framework Catalysts for Carboxylative Cyclization of Propargylamines with Carbon Dioxide
  作者：Dan Zhao、Xiao-Hui Liu、Chendan Zhu、Yan-Shang Kang、Peng Wang、Zhuangzhi Shi、Yi Lu、Wei-Yin Sun

  DOI：10.1002/cctc.201701190

  日期：2017.12.20

  fix it into valuable chemical products, functionalized dynamic metal–organic frameworks (MOFs) have been utilized not only because of their inherent cavity for accommodating CO2 but also owing to their reversible structural transformations in response to external stimuli for regulating the reaction. Herein, we report a dynamic and functional MOF [Cd3(L)2(BDC)3]2⋅16 DMF (MOF‐1 a; DMF=N,N‐dimethylformamide)

  二氧化碳（CO 2）的捕获和转化对于降低大气中CO 2的浓度很重要。为了有效地捕获CO 2并将其进一步固定在有价值的化学产品中，功能化的动态金属有机框架（MOF）不仅由于其固有的空腔可容纳CO 2而被利用，而且还由于其响应外部刺激而可逆的结构转变而被利用。用于调节反应。此，我们报告一个动态和功能MOF [CD 3（L）2（BDC）3 ] 2 ⋅ 16 DMF（MOF-1 ; DMF = Ñ，Ñ氨基三脚架咪唑配体N 1-（4-（1  H-咪唑-1-基）苄基）-N 1-（2-氨基乙基）乙烷-1,2-二胺（L）与1,4-苯二甲酸（H 2 BDC）与镉盐。MOF-1a不仅显示出空前的高催化活性[起始周转率（TON）高达9300]和广泛的底物范围，用于炔丙基胺与CO 2的羧基环化，而且由于它的动态五重互穿结构。进一步的研究表明，MOF-1 a 与复杂的生物系统相似，它显示出取决于底物大小的选择性催化特性。
• Carboxylative cyclization of propargylic amines with CO2 catalyzed by dendritic N-heterocyclic carbene–gold(I) complexes
  作者：Ken-ichi Fujita、Kensuke Inoue、Junichi Sato、Teruhisa Tsuchimoto、Hiroyuki Yasuda

  DOI：10.1016/j.tet.2016.01.016

  日期：2016.3

  complex. In particular, by employing an amphiphilic dendritic NHC–gold(I) complex having penta(ethylene glycol) units at the peripheral layer as a catalyst, the aqueous media carboxylative cyclization of propargylic amines proceeded smoothly to provide the corresponding 2-oxazolidinone at room temperature under atmospheric pressure of CO2.

  我们准备了几种新型的树枝状N-杂环卡宾（NHC）-金（I）配合物。特别是，通过使用在外围层具有五（乙二醇）单元的两亲树状NHC-金（I）络合物作为催化剂，炔丙基胺的水介质羧基化环化可顺利进行，从而在室温下提供相应的2-恶唑烷酮在CO 2的大气压下。
• A green approach for the synthesis of 2-oxazolidinones using gold(I) complex immobilized on KCC-1 as nanocatalyst at room temperature
  作者：Seyed Mohsen Sadeghzadeh

  DOI：10.1002/aoc.3511

  日期：2016.10

  A novel gold(I)‐containing ionic liquid‐based KCC‐1 catalyst was applied for the cyclization of propargylic amines with CO2 to provide 2‐oxazolidinones. High catalytic activity and ease of recovery from the reaction mixture using an external magnet, and several recycle runs without significant loss in performance are additional eco‐friendly attributes of this catalytic system. Copyright © 2016 John

  一种新型的含金（I）的基于离子液体的KCC-1催化剂用于将炔丙基胺与CO 2进行环化以提供2-恶唑烷酮。此催化系统的其他环保特性是，高催化活性和使用外部磁体易于从反应混合物中回收以及数次循环运行而不会显着降低性能的情况。版权所有©2016 John Wiley＆Sons，Ltd.
• Ni@Pd nanoparticles supported on ionic liquid-functionalized KCC-1 as robust and recyclable nanocatalysts for cycloaddition of propargylic amines and CO₂
  作者：Seyed Mohsen Sadeghzadeh、Rahele Zhiani、Shokufe Emrani

  DOI：10.1002/aoc.3941

  日期：2018.1

  heterogeneous catalyst systems comprised of a fibrous nanosilica‐supported nano‐Ni@Pd‐based ionic liquid (KCC‐1/IL/Ni@Pd) are described for the cyclization of propargylic amines with CO2 to provide 2‐oxazolidinones. KCC‐1 with high surface area was functionalized with IL acting as a robust anchor so that the nano‐Ni@Pd was well dispersed on the fibres of the KCC‐1 microspheres, without aggregation. Because

  描述了一种新型的非均相催化剂体系，该体系由纤维纳米二氧化硅支撑的基于纳米Ni @ Pd的离子液体（KCC-1 / IL / Ni @ Pd）组成，用于将炔丙基胺与CO 2环化以提供2-恶唑烷酮。高表面积的KCC-1被IL用作坚固的锚定物进行了功能化，因此nano-Ni @ Pd很好地分散在KCC-1微球的纤维上，没有聚集。由于IL的放大作用，实现了纳米催化剂的高负载能力。报告的合成方法包括无溶剂条件，操作简便，反应时间短，对环境无害的反应条件，成本效益，高原子经济性和优异的收率等诸多优点，使其成为真正的绿色方案。
• Efficient synthesis of 2-oxazolidinones and quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by tetrabutylammonium fluoride
  作者：Akira Fujii、Hideaki Matsuo、Jun-Chul Choi、Tadahiro Fujitani、Ken-ichi Fujita

  DOI：10.1016/j.tet.2018.04.059

  日期：2018.6

  case, it was also found that the generated 2-oxazolidinones were tautomerized into the corresponding 2-oxazolones due to the basicity of TBAF. In addition, we performed the synthesis of quinazoline-2,4(1H,3H)-dione from 2-aminobenzonitrile and CO2 by using TBAF as a catalyst.

  通过使用氟化四丁基铵（TBAF）作为催化剂，具有内部炔烃的炔丙基胺与CO 2的各种羧基环化反应进行，得到相应的2-恶唑烷酮。在这种情况下，还发现由于TBAF的碱性，所产生的2-恶唑烷酮被互变异构成相应的2-恶唑酮。此外，我们以TBAF为催化剂，由2-氨基苄腈和CO 2合成了喹唑啉-2,4（1 H，3 H）-二酮。