N-benzyl-1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-amine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-benzyl-1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-amine
• 化学式: C₂₃H₂₁NO
• 分子量: 327.426
• InChiKey: RPTRRGKUHWDNMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-amine 在 二甲基亚砜 、 potassium hydroxide 作用下， 反应 1.0h， 以85%的产率得到5-(4-methoxyphenyl)-2,3-diphenyl-1H-pyrrole
  参考文献：
  名称：

  Base-Mediated Direct Transformation of N-Propargylamines into 2,3,5-Trisubstituted 1H-Pyrroles

  摘要：

  An efficient and base-mediated intramolecular cyclization of N-propargylamines for the synthesis of structurally diversified pyrroles in high yield has been described. The developed methodology is broadly applicable and is tolerated by a variety of functional groups. Key intermediates of natural product discoipyrrole C as well as HMG-CoA-reductase inhibitor have been successfully synthesized using developed chemistry. The proposed mechanism was supported by control experiments.

  DOI：

  10.1021/acs.orglett.8b03112
• 作为产物：
  描述：

  (E)-N-benzyl-1-(4-methoxyphenyl)methanimine 、 苯乙炔 在 三乙胺 、 zinc(II) chloride 、 三甲基氯硅烷 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以62%的产率得到N-benzyl-1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-amine
  参考文献：
  名称：

  Lewis acid promoted alkynylation of imines with terminal alkynes: simple, mild and efficient preparation of propargylic amines

  摘要：

  A mild and efficient addition of terminal alkynes to imines in the presence of ZnCl2, Et3N and TMSCl gives propargylamines in good yields. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01674-5

文献信息

• Synthesis of Fully Substituted Pyrroles through a Copper-Catalyzed Aza-Michael/Claisen Rearrangement/Cyclization Cascade
  作者：Hao Tan、Xue-Fei Jiang、Lu Jiang、Chang Yuan、Xue Tang、Meng-Fan Li、Si-Wei Liu、Si Liu、Hai-Lei Cui

  DOI：10.1055/s-0039-1691577

  日期：2020.4

  We have developed a copper-catalyzed aza-Michael/Claisen rearrangement/cyclization cascade sequence that affords structurally diverse pentasubstituted pyrroles in acceptable to good yields (31–84%).

  我们开发了一种铜催化的氮杂-迈克尔/克莱森重排/环化级联序列，以可接受的良好收率（31-84%）提供结构多样的五取代吡咯。
• Synthesis of Imidazolidin-2-ones and Imidazol-2-ones via Base-Catalyzed Intramolecular Hydroamidation of Propargylic Ureas under Ambient Conditions
  作者：Alessandra Casnati、Antonio Perrone、Paolo P. Mazzeo、Alessia Bacchi、Raffaella Mancuso、Bartolo Gabriele、Raimondo Maggi、Giovanni Maestri、Elena Motti、András Stirling、Nicola Della Ca’

  DOI：10.1021/acs.joc.9b00064

  日期：2019.3.15

  The first organo-catalyzed synthesis of imidazolidin-2-ones and imidazol-2-ones via intramolecular hydroamidation of propargylic ureas is reported. The phosphazene base BEMP turned out to be the most active organo-catalyst compared with guanidine and amidine bases. Excellent chemo- and regioselectivities to five-membered cyclic ureas have been achieved under ambient conditions, with a wide substrate

  据报道，通过炔丙基脲的分子内加氢酰胺化反应，首次有机催化合成了咪唑烷基-2-酮和咪唑-2-酮。与胍和am碱相比，磷腈碱BEMP被证明是活性最高的有机催化剂。在环境条件下，五元环状脲具有出色的化学和区域选择性，具有广泛的底物范围和异常短的反应时间（低至1分钟）。DFT研究表明，碱介导的烯丙酰胺中间体异构化步骤是产生咪唑-2-酮的最可行反应途径。
• Tuning the Reactivity of Isocyano Group: Synthesis of Imidazoles and Imidazoliums from Propargylamines and Isonitriles in the Presence of Multiple Catalysts
  作者：Shuo Tong、Qian Wang、Mei-Xiang Wang、Jieping Zhu

  DOI：10.1002/anie.201410113

  日期：2015.1.19

  tert‐butylisonitrile in the presence of a catalytic amount of both Yb(OTf)3 and AgOTf afforded imidazoles, whereas the same reaction with primary and secondary alkylisonitriles, as well as arylisonitriles, in the presence of three metal salts [Yb(OTf)3/AgOTf/KOTf] resulted in the 1,3,4,5‐tetrasubstituted imidazoliums in excellent yields. Both chiral amines and chiral isonitriles can be used to provide corresponding

  在催化量的Yb（OTf）3和AgOTf的存在下，炔丙基胺与叔丁基异腈的反应得到了咪唑，而在三种金属盐的存在下，伯，仲烷基异腈以及芳基异腈的反应相同。 [Yb（OTf）3 / AgOTf / KOTf]产生1,3,4,5-四取代的咪唑类，产率极高。手性胺和手性异腈均可用于提供相应的手性杂环而没有外消旋作用。在这种多催化体系中，Yb（OTf）3催化了异腈向N的插入胺的H键，AgOTf催化所得的am氮与拴系的三键的5-exo-dig环化反应，而KOTf促进了盐的复分解，从而同时提供了对咪唑鎓的抗衡离子。根据常识，异氰基在这些反应中起极化三键的作用，而不是常规的卡宾样功能。
• Activation of Primary Amines by Copper(I)-Based Lewis Acid Promoters in the Solventless Synthesis of Secondary Propargylamines
  作者：Cristina Cimarelli、Federica Navazio、Federico Rossi、Fabio Del Bello、Enrico Marcantoni

  DOI：10.1055/s-0037-1612253

  日期：2019.6

  reaction provided good yields and a wider applicability, with the added value given by a safer procedure. Primary amines are activated by copper(I)-based Lewis acid promoters in an A3-coupling one-pot solventless reaction with aldehydes and phenylacetylene for the synthesis of secondary propargylamines. The reaction is promoted by a CuSO4/NaI system, a practical precursor of the in situ generated effective

  抽象的 伯胺在与醛和苯乙炔的A 3偶联一锅法无溶剂反应中被基于铜（I）的路易斯酸助催化剂活化，以合成仲炔丙胺。CuSO 4 / NaI系统（原位生成的有效CuI / I 2系统的实用前体）促进了反应，该方法效果很好，但仅在有限的几个示例中有效。一锅两步反应中用CeCl 3 ·7H 2 O取代I 2可以提供良好的收率和更广泛的适用性，并通过更安全的程序获得附加值。 伯胺在与醛和苯乙炔的A 3偶联一锅法无溶剂反应中被基于铜（I）的路易斯酸助催化剂活化，以合成仲炔丙胺。CuSO 4 / NaI系统（原位生成的有效CuI / I 2系统的实用前体）促进了反应，该方法效果很好，但仅在有限的几个示例中有效。一锅两步反应中用CeCl 3 ·7H 2 O取代I 2可以提供良好的收率和更广泛的适用性，并通过更安全的程序获得附加值。
• Boosting Energy‐Transfer Processes via Dispersion Interactions
  作者：Alessandro Cerveri、Gabriele Scarica、Sara Sparascio、Matteo Hoch、Maurizio Chiminelli、Matteo Tegoni、Stefano Protti、Giovanni Maestri

  DOI：10.1002/chem.202304010

  日期：2024.3.12

  We present the generalized beneficial effect of naphthalene and its simple derivatives on energy-transfer reactions. Increased reactions rates and higher yields are achieved for several reactivities, varying substrates, solvents, light sources and photocatalysts. The consistent trend is observed using molar excess of naphthalene or a catalytic amount of tailored bi-naphthyl derivatives. These findings

  我们提出了萘及其简单衍生物对能量转移反应的普遍有益作用。通过多种反应性、不同的底物、溶剂、光源和光催化剂，可以实现更高的反应速率和更高的产率。使用摩尔过量的萘或催化量的定制联萘衍生物观察到一致的趋势。这些发现可广泛用于改进现有方法并减少开发新方法所需的工作量。