4-(3-(4-methoxyphenyl)prop-2-ynyl)morpholine | 1438890-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(3-(4-methoxyphenyl)prop-2-ynyl)morpholine
• 英文别名: 4-[3-(4-Methoxyphenyl)prop-2-ynyl]morpholine；4-[3-(4-methoxyphenyl)prop-2-ynyl]morpholine
• CAS: 1438890-13-1
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: FZIZRJSJCCCFGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  352.8±37.0 °C(predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吗啉 、 3-(4-甲氧基苯基)丙酸 在 聚合甲醛 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以85%的产率得到4-(3-(4-methoxyphenyl)prop-2-ynyl)morpholine
  参考文献：
  名称：

  Metal-Free Decarboxylative Three-Component Coupling Reaction for the Synthesis of Propargylamines

  摘要：

  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.

  DOI：

  10.1021/ol401358t

文献信息

• Two inorganic–organic hybrid silver-polyoxometalates as reusable catalysts for one-pot synthesis of propargylamines <i>via</i> a three-component coupling reaction at room temperature
  作者：Ming-Yu Dou、Xian-Qiang Huang、Guo-Yu Yang

  DOI：10.1039/d0ce00042f

  日期：——

  Importantly, compound 1 showed high catalytic activities for the three-component coupling reaction of alkynes and secondary amines along with formaldehyde, which resulted in a series of propargylamine derivatives in higher yields (up to 99%). Furthermore, the Ag–POM catalyst was easily recovered by filtration and reused for three cycles without a significant loss in catalytic activity. A tentative mechanism

  通过银络合物和Keggin POM的组合，形成了两种新型的无机-有机银-多金属氧酸盐杂化物[Ag 3 L 2（DMSO）2 ] [PW 12 O 40 ]·4DMSO（1）和[（Ag 2 L 2）2 ] [SiW 12 O 40 ]·10DMSO·2H 2 O（2）（L ＝ 4-（2-吡啶基）-6-（4-吡啶基）-2-氨基嘧啶）被合成和表征。有趣的是，化合物1中的银原子与AgNO模型三配位；但是，化合物2的Ag原子被有机配体的四个N原子包围并显示出扭曲的四面体构型。重要的是，化合物1对炔烃和仲胺与甲醛的三组分偶联反应显示出高催化活性，从而以更高的收率（高达99％）产生了一系列炔丙基胺衍生物。此外，Ag-POM催化剂很容易通过过滤回收，并可以重复使用三个循环而不会显着降低催化活性。还为这种转换提出了一种尝试性机制。
• Construction of Four Copper Coordination Polymers Derived from a Tetra-Pyridyl-Functionalized Calix[4]arene: Synthesis, Structural Diversity, and Catalytic Applications in the A³ (Aldehyde, Alkyne, and Amine) Coupling Reaction
  作者：Cai-Xia Yu、Fei-Long Hu、Meng-Yu Liu、Cai-Wen Zhang、Yun-He Lv、Shu-Kuan Mao、Lei-Lei Liu

  DOI：10.1021/acs.cgd.7b00898

  日期：2017.10.4

  Solvothermal reactions of CuX2 (X = NO3, Cl, Br, I) with tetra-pyridyl-functionalized calix[4]arene at 130 °C afforded four novel coordination polymers, [(CuNO3)2L]·MeOH}n (1), [(CuCl2)L0.5]n (2), [(Cu3Br3)L]n (3), and [(Cu3I3)L]n (4), where L = 25,26,27,28-tetra[(3-pyridylmethyl)oxy]calix[4]arene. All the products were characterized by infrared spectroscopy, thermogravimetric analysis, single-crystal

  CuX 2（X = NO 3，Cl，Br，I）与四吡啶基官能化杯[4]芳烃在130°C的溶剂热反应制得四种新型配位聚合物，[（（CuNO 3）2 L]·MeOH} n（1），[（CuCl 2）L 0.5 ] n（2），[（Cu 3 Br 3）L] n（3）和[（Cu 3 I 3）L] n（4），其中L = 25,26,27,28-四[（3-吡啶基甲基）氧基]杯[4]芳烃。所有产品均通过红外光谱，热重分析，单晶X射线衍射和粉末X射线衍射进行表征。晶体结构分析表明，1拥有由单核[Cu（NO 3）]单元和L个连接基构成的一维（1D）双链，而2个具有1D链，其碗形L配体起着连接连接基的作用。双核[Cu 2 Cl 4 ]单元。化合物3和4具有相似的二维网络，其中每个三核[Cu 3 Br 3 ] / [Cu 3 I3 ]单元充当三个连接节点，通过共享L个配体连接其六个等价物。这些结果表明，不同的阴离
• Dual Catalysis of Gold Nanoclusters: Photocatalytic Cross‐Dehydrogenative Coupling by Cooperation of Superatomic Core and Molecularly Modified Staples**
  作者：Katsuhiro Isozaki、Kenta Iseri、Ryohei Saito、Kyosuke Ueda、Masaharu Nakamura

  DOI：10.1002/anie.202312135

  日期：2024.1.8

  nanoclusters were found to show a dual catalysis toward photocatalytic cross-dehydrogenative coupling reactions between aliphatic tertiary amines and terminal alkynes to produce propargylamine products. The dual catalysis was enabled by the cooperation of the superatomic core and staple moieties for the photooxidation of amines and the carbon-carbon bond formation.

  发现金纳米簇对脂肪族叔胺和末端炔烃之间的光催化交叉脱氢偶联反应显示出双重催化作用，以产生丙炔胺产物。通过超原子核心和主链部分的协同作用，实现胺的光氧化和碳-碳键形成的双重催化作用。
• A copper-free, cross-coupling of terminal alkynes with hetaryl halides
  作者：Pavel Arsenyan、Kira Rubina、Jelena Vasiljeva、Sergey Belyakov

  DOI：10.1016/j.tetlet.2013.09.088

  日期：2013.11

  Substituted ethynyl heterocycles and heteroarylbutenynes are synthesized efficiently in good yields via a copper-free, cross-coupling reaction. (C) 2013 Elsevier Ltd. All rights reserved.
• Efficient One-Pot Synthesis of Propargylamines from Mannich Bases through a Retro-Mannich-Type Fragmentation
  作者：Yunyang Wei、Yefeng Zhu、Huishuang Zhao

  DOI：10.1055/s-0032-1316862

  日期：——

  An efficient one-pot synthesis of propargylamines is achieved by copper-catalyzed coupling of phenylacetylenes with Mannich bases through a chlorine(1+) or bromine(1+) ion-initiated retro-Mannich-type fragmentation under mild conditions. The Mannich bases are easily prepared from an electron-rich phenol, formaldehyde, and an amine. The protocol provides an appealing alternative for the construction of propargylamines by a simple one-pot procedure.