1-[1-(3-氯苯基)-3-苯基丙-2-炔基]哌啶 | 592521-50-1

• 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
• 中文名称: 1-[1-(3-氯苯基)-3-苯基丙-2-炔基]哌啶
• 英文名称: 1-(1-(3-chlorophenyl)-3-phenylprop-2-yn-1-yl) piperidine
• 英文别名: N-(1-(3-chlorophenyl)-3-phenyl-2-propynyl)piperidine；N-[1-(3-chlorophenyl)-3-phenyl-2-propynyl]piperidine；Piperidine, 1-[1-(3-chlorophenyl)-3-phenyl-2-propynyl]-；1-[1-(3-chlorophenyl)-3-phenylprop-2-ynyl]piperidine
• CAS: 592521-50-1
• 化学式: C₂₀H₂₀ClN
• 分子量: 309.838
• InChiKey: BGIDOLBKFJYBEB-UHFFFAOYSA-N

物化性质

• 沸点：
  422.9±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-(3-chloro-selenobenzoyl)piperidine 、 苯乙炔 在 铜 作用下， 反应 4.0h， 以80%的产率得到1-[1-(3-氯苯基)-3-苯基丙-2-炔基]哌啶
  参考文献：
  名称：

  Copper(0)-Induced Deselenative Insertion of N,N-Disubstituted Selenoamides into Acetylenic C−H Bond Leading to Propargylamines

  摘要：

  Upon heating at 110 degrees C in the presence of copper(0) powder, terminal acetylenes undergo a novel deselenative C-H bond insertion reaction of N,N-substituted selenoamides, affording the corresponding propargylamines in good to excellent yields, selectively.

  DOI：

  10.1021/ol9001976

文献信息

• Manganese(<scp>ii</scp>) chloride catalyzed highly efficient one-pot synthesis of propargylamines and fused triazoles via three-component coupling reaction under solvent-free condition
  作者：Shakil N. Afraj、Chinpiao Chen、Gene-Hsian Lee

  DOI：10.1039/c4ra03232b

  日期：——

  A one-pot green and highly efficient method for the synthesis of propargylamines and diastereoselective synthesis of fused triazoles via three-component coupling in the presence of manganese(II) chloride as a catalyst and a catalyst-free 1,3-dipolar cycloaddition reaction, respectively, without using a co-catalyst or activator is reported. This methodology is efficient, eco-friendly, operationally

  一锅绿色高效的炔丙胺合成和稠合三唑的非对映选择性合成方法，该方法在氯化锰（II）作为催化剂和无催化剂的1,3-偶极环加成反应下，通过三组分偶联进行，分别报道了不使用助催化剂或活化剂的情况。这种方法对于涉及芳族，脂族和杂环醛的反应而言是高效，环保的，操作简单且有效的，并且可以轻松获得高产率的炔丙基胺，高产率的熔融三唑和非对映选择性。
• Ag2CO3-catalyzed efficient synthesis of internal or terminal propargylicamines and chalcones via A3-coupling under solvent-free condition
  作者：Ningbo Li、Shitang Xu、Xueyan Wang、Li Xu、Jie Qiao、Zhiwu Liang、Xinhua Xu

  DOI：10.1016/j.cclet.2021.04.026

  日期：2021.12

  or terminal propargylamines and chalcones via A3-coupling reaction of aldehydes, amines, and alkynes catalyzed by an easily available catalyst Ag2CO3 under solvent-free condition. The reaction proceeded smoothly to deliver various products in good-to-excellent yields with good functional group tolerance. Gram-scale preparation, bioactive molecule synthesis and asymmetric substrates have been demonstrated

  几个简单，快速和实用的协议已被开发来合成内部或末端炔丙胺和查耳酮通过甲3 -耦合醛，胺的反应，和炔由容易获得的催化剂催化的Ag 2 CO 3无溶剂条件下进行。反应进行得很顺利，以良好的收率和良好的官能团耐受性提供了各种产品。已经证明了克级制备，生物活性分子合成和不对称底物。此外，已经提出了合成不同产物的合理机制。
• The First Cobalt-Catalyzed Transformation of Alkynyl C-H Bond: Aldehyde-Alkyne-Amine (A³) Coupling
  作者：Chao-Jun Li、Wen-Wen Chen、Hai-Peng Bi

  DOI：10.1055/s-0029-1219173

  日期：2010.2

  The first highly effective cobalt-catalyzed reaction of terminal alkynes was developed. The reaction of alkynes with aldehyde and amine generated a diverse range of propargyl amines in excellent yields by this method.

  首次开发了高效的钴催化末端炔烃反应。通过这种方法，炔烃与醛和胺的反应生成了多种多样的丙炔胺，产率优异。
• Efficient three-component coupling catalysed by mesoporous copper–aluminum based nanocomposites
  作者：Jana Dulle、K. Thirunavukkarasu、Marjo C. Mittelmeijer-Hazeleger、Daria V. Andreeva、N. Raveendran Shiju、Gadi Rothenberg

  DOI：10.1039/c3gc36607c

  日期：——

  Traditional synthesis methods for propargylamines have several drawbacks. A recently developed alternative route is the so-called “A3 coupling” in which an alkyne, an aldehyde, and an amine are coupled together. Typically, these reactions are catalysed by homogeneous gold salts, organogold complexes or silver salts. But these homogeneous catalysts are expensive and their separation is difficult. Here we report the discovery that solid Cu/Al/oxide mesoporous “sponges” are excellent A3 coupling catalysts. These materials are robust, inexpensive, and easy to make. They give good to excellent yields (87–97%) for a wide range of substrates. Being heterogeneous, these catalysts are also easy to handle and separate from the reaction mixture, and can be recycled with no loss of activity.

  传统的丙炔胺合成方法存在一些缺点。最近开发的一种替代路线是所谓的“A3偶联”，在该过程中，一种炔烃、一种醛和一种胺被偶联在一起。通常，这些反应是由均相金盐、有机金络合物或银盐催化的。但这些均相催化剂成本高且分离困难。在这里，我们报告了固体Cu/Al/氧化物介孔“海绵”作为优秀的A3偶联催化剂的发现。这些材料坚固、廉价且易于制作。它们对广泛的底物提供良好到优异的产率（87-97%）。作为非均相催化剂，这些催化剂也易于处理和从反应混合物中分离，且能在不损失活性的情况下重复使用。
• Engineering metal–organic frameworks immobilize gold catalysts for highly efficient one-pot synthesis of propargylamines
  作者：Liu Lili、Zhang Xin、Gao Jinsen、Xu Chunming

  DOI：10.1039/c2gc35284b

  日期：——

  heterogeneous catalysts have been of extreme interest since they could bridge the gap between homogeneous and heterogeneous catalysis. We have designed and synthesized gold functionalized IRMOF-3 catalysts by post-covalent modification (PM) and one-pot (OP) synthesis methods. The gold functionalized IRMOF-3 catalysts provide an efficient, economic, and novel route for the one-pot synthesis of structurally

  异质性工程金属有机框架（MOF） 催化剂由于它们可以弥合均相催化和非均相催化之间的差距，因此一直备受关注。我们已经设计并合成了金功能化的IRMOF-3催化剂通过共价后修饰（PM）和一锅法（OP）合成方法。黄金功能化IRMOF-3催化剂通过三组分偶联反应为结构上不同的炔丙基胺的一锅合成提供了一种有效，经济和新颖的途径炔烃， 胺， 和 醛（A 3）没有任何添加剂或惰性气氛。这催化剂对它们进行了深入表征，以了解它们的结构与属性之间的关系。结果表明4.6％Au / IRMOF-3催化剂通过PM法制得的，含有一部分阳离子金（Au 3+ / Au 0 = 0.2），与通过OP法制得的3.2％或0.6％Au / IRMOF-3相比，其催化活性高得多。前者的结晶度比后两者低得多催化剂。值得注意的是，Au / IRMOF-3的催化活性催化剂在适中的反应温度（150°C）下可以显着提高。全部Au / IRMOF-3催化剂