benzyl-methyl-(3-p-tolylprop-2-ynyl)-amine

• 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: benzyl-methyl-(3-p-tolylprop-2-ynyl)-amine
• 英文别名: N-benzyl-N-methyl-3-(p-tolyl)prop-2-yn-1-amine；N-benzyl-N-methyl-3-(4-methylphenyl)prop-2-yn-1-amine
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: ALSGTVNKJATZEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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,N-二甲基苄胺 、 4-甲苯基乙炔 在 叔丁基过氧化氢 、 Cu₆Se_4.5 作用下， 以 水 为溶剂， 反应 3.0h， 以67%的产率得到benzyl-methyl-(3-p-tolylprop-2-ynyl)-amine
  参考文献：
  名称：

  来自单一来源前体的 Cu6Se4.5 纳米颗粒：用于叔胺与末端炔烃交叉脱氢偶联的可回收高效催化剂

  摘要：

  摘要 首次证明了在叔丁基过氧化氢作为氧化剂存在下，硒化铜纳米催化剂用于叔胺与末端炔烃的高效区域选择性交叉脱氢偶联（CDC）。该催化剂由单一来源的前体 CuSePh 合成的独特的 Cu6Se4.5 纳米粒子组成，所需的量（1 mol%）要低得多，并且可回收多达四个反应循环，活性略有损失。该反应可在无溶剂条件下进行，适用于芳香族、苄基和脂肪族叔胺，并以中等至良好的收率提供炔丙基胺。

  DOI：

  10.1016/j.molcata.2016.06.005

文献信息

• Cu6Se4.5 Nanoparticles from a single source precursor: Recyclable and efficient catalyst for cross-dehydrogenative coupling of tertiary amines with terminal alkynes
  作者：Sonu Gupta、Hemant Joshi、Nidhi Jain、Ajai K. Singh

  DOI：10.1016/j.molcata.2016.06.005

  日期：2016.11

  Abstract The use of copper selenide nanocatalyst for an efficient and regioselective cross-dehydrogenative coupling (CDC) of tertiary amines with terminal alkynes in the presence of tert-butyl hydroperoxide as the oxidant is demonstrated for the first time. The catalyst comprising of unique Cu6Se4.5 nanoparticles synthesized from a single source precursor CuSePh, is required in much lower amount (1 mol%)

  摘要 首次证明了在叔丁基过氧化氢作为氧化剂存在下，硒化铜纳米催化剂用于叔胺与末端炔烃的高效区域选择性交叉脱氢偶联（CDC）。该催化剂由单一来源的前体 CuSePh 合成的独特的 Cu6Se4.5 纳米粒子组成，所需的量（1 mol%）要低得多，并且可回收多达四个反应循环，活性略有损失。该反应可在无溶剂条件下进行，适用于芳香族、苄基和脂肪族叔胺，并以中等至良好的收率提供炔丙基胺。
• Copper-Catalyzed Coupling of Tertiary Aliphatic Amines with Terminal Alkynes to Propargylamines via C−H Activation
  作者：Mingyu Niu、Zhengming Yin、Hua Fu、Yuyang Jiang、Yufen Zhao

  DOI：10.1021/jo800279j

  日期：2008.5.1

  convenient and efficient method for coupling of tertiary aliphatic amines with terminal alkynes to propargylamines via C−H activation. The protocol uses CuBr as the catalyst, NBS as the free radical initiator, CH3CN as the solvent, and the alkynylation was selectively performed on the methyl of tertiary aliphatic amines at 80 °C. This is an economical and practical method for the synthesis of propargylamines

  我们已经开发了一种方便高效的方法，用于通过CH活化将末端脂肪族叔脂肪胺与炔丙基胺偶联。该方案使用CuBr作为催化剂，NBS作为自由基引发剂，CH 3 CN作为溶剂，并在80°C的条件下对脂肪族叔胺的甲基进行了烷基化反应。这是合成炔丙基胺的经济实用的方法。
• A microwave-enhanced, solventless Mannich condensation of terminal alkynes and secondary amines with para-formaldehyde on cuprous iodide doped alumina
  作者：George W. Kabalka、Li-Li Zhou、Lei Wang、Richard M. Pagni

  DOI：10.1016/j.tet.2005.10.049

  日期：2006.1

  A microwave-enhanced, solventless Mannich condensation of terminal alkynes and secondary amines with para-formaidehyde on cuprous iodide doped alumina has been developed. beta-Aminoalkynes are generated in good yields. The reaction can be extended to include a cyclization, which affords 2-substituted benzo[b]furans. The chemoselectivity of the reaction indicates that terminal alkynes are much more reactive than enolizable ketones under the reaction conditions. (c) 2005 Elsevier Ltd. All rights reserved.
• Metal-Free Decarboxylative Three-Component Coupling Reaction for the Synthesis of Propargylamines
  作者：Kyungho Park、Yumi Heo、Sunwoo Lee

  DOI：10.1021/ol401358t

  日期：2013.7.5

  A metal-free decarboxylative three-component coupling reaction was developed. When alkynyl carboxylic acids, paraformaldehyde, and amines were reacted in CH3CN at 65 degrees C for 3 h, the desired propargylamines were obtained in good yields. This coupling reaction also showed good yield in water solvent. This reaction showed higher selectivity toward alkynyl carboxylic acids than a terminal alkyne.
• Oxidative C–C bond formation and C–N bond cleavage catalyzed by complexes of copper(<scp>i</scp>) with acridine based (E N E) pincers (E = S/Se), recyclable as a catalyst
  作者：Sonu Gupta、Pooja Dubey、Ajai K. Singh、Nidhi Jain

  DOI：10.1039/c9dt01766f

  日期：——

  Copper(I) complexes of 4,5-bis((phenylthio/seleno)methyl)acridine, [CuLBr] (C1 and C2) (L = L1/L2; pincer type (E N E) ligand), were synthesized and found to be thermally stable, and moisture and air insensitive. The complexes and ligands were characterized by multinuclei NMR and single crystal X-ray diffraction. In both complexes C1 and C2, ligands L1 and L2 coordinate with Cu in a pincer mode furnishing

  合成并发现了4,5-双（（苯硫基/硒代）甲基），啶的铜（I）配合物[Cu L Br]（C1和C2）（L = L1 / L2；钳型（ENE）配体）具有热稳定性，对湿气和空气不敏感。配合物和配体通过多核NMR和单晶X射线衍射进行表征。在复合物C1和C2中，配体L1和L2与铜以钳位模式配位，提供两个六元螯合环，施主原子的四面体几何形状在铜周围变形。Cu–S和Cu–Se键长（Å）分别为2.2482（17）–2.2979（16）和2.3603（14）–2.4177（13）。这些络合物是未活化的叔胺与未活化的末端炔烃交叉脱氢偶联以及在无氧化溶剂的条件下裂解N，N二甲基苄胺的苄基（C–N）键的有效催化剂。发现反应是高度选择性的，并且未观察到对酸的过度氧化。1.0mol％的低催化负载量足以使这两种转化具有高达五倍的可回收性。