4-(3-phenyl-1-phenylethynyl-prop-2-ynyl)morpholine | 853995-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(3-phenyl-1-phenylethynyl-prop-2-ynyl)morpholine
• 英文别名: 4-(1,5-diphenylpenta-1,4-diyn-3-yl)morpholine；4-(1,5-diphenylpent-1,4-diynyl)morpholine；4-(1,5-Diphenylpenta-1,4-diyn-3-yl)morpholine
• CAS: 853995-38-7
• 化学式: C₂₁H₁₉NO
• 分子量: 301.388
• InChiKey: CVLJKOZONYOSNW-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  449.9±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙炔 以 甲苯 为溶剂， 反应 3.0h， 生成 4-(3-phenyl-1-phenylethynyl-prop-2-ynyl)morpholine
  参考文献：
  名称：

  通过在N，N-双取代的甲酰胺和N，O-缩醛中添加炔基二甲基铝试剂合成N，N-二取代的3-氨基-1,4-二炔和3-氨基-1-炔

  摘要：

  将一系列炔基二甲基铝试剂添加到N，N-二取代的甲酰胺及其缩醛中，以提供相应的N，N-二取代的3-氨基-1,4-二炔。同样，这些试剂平稳地添加到N，O-乙缩醛中，得到相应的N，N-二取代的3-amino-1-ynes。

  DOI：

  10.1002/ejoc.201402464

文献信息

• Copper-Catalyzed A3-Coupling: Synthesis of 3-Amino-1,4-diynes
  作者：Yoon-Jeong Choi、Hye-Young Jang

  DOI：10.1002/ejoc.201600343

  日期：2016.6

  the synthesis of 3-amino-1,4-diynes. Although metal-catalyzed A3-coupling reactions have been extensively used to synthesize various propargylamines, the A3-coupling for the synthesis of 3-amino-1,4-diynes has been rarely reported. In this study, various symmetrical 3-amino-1,4-diynes were synthesized by the sequential Cu-catalyzed dealkynylation of propargyl aldehydes followed by A3-coupling. Unsymmetrical

  研究了铜催化的 A3（胺、醛和炔）偶联反应以合成 3-氨基-1,4-二炔。尽管金属催化的 A3-偶联反应已被广泛用于合成各种炔丙胺，但很少报道用于合成 3-氨基-1,4-二炔的 A3-偶联反应。在这项研究中，通过连续铜催化炔丙醛脱炔化和 A3 偶联合成了各种对称的 3-氨基-1,4-二炔。不对称的 3-氨基-1,4-二炔也通过铜催化的 A3 偶联以 49-85% 的产率合成。
• Sequential Addition Reactions of Two Molecules of Grignard Reagents to Thioformamides
  作者：Toshiaki Murai、Kazuki Ui、Narengerile

  DOI：10.1021/jo900915n

  日期：2009.8.7

  Sequential addition reactions of two molecules of Grignard reagents to thioformamides were found to yield tertiary amines in an efficient manner. The addition of two different Grignard reagents can be accomplished by using one equivalent of arylmagnesium reagent in the first step. In the second step, a variety of reagents such as alkyl, alkenyl, aryl, and alkynyl reagents were used to afford the corresponding

  发现两个分子的格氏试剂与硫代甲酰胺的顺序加成反应可以有效地产生叔胺。可以通过在第一步中使用一当量的芳基镁试剂来完成两种不同的格氏试剂的添加。在第二步中，使用各种试剂（例如烷基，烯基，芳基和炔基试剂）以高收率或高收率得到相应的胺。
• Addition reaction of zinc acetylides to thioiminium salts leading to 3-amino-1-sulfenyl-1,4-enynes
  作者：Toshiaki Murai、Yukiyasu Ohta、Yuichiro Mutoh

  DOI：10.1016/j.tetlet.2005.03.166

  日期：2005.5

  The reaction of thioiminium salts with zinc acetylides took place at 60 °C to give 3-amino-1-sulfenyl-1,4-enynes in moderate to good yields. Two molecules of acetylides were incorporated into the products. Nucleophilic attack of zinc acetylides to thioiminium salts may initially occur to form alkynyl S,N-acetals, followed by their [1,3]-rearrangement to give 3-sulfenyl-1-aminoallenes.

  硫亚亚胺盐与乙炔锌的反应在60°C进行，以中等至良好的收率得到3-氨基-1-亚磺酰基-1,4-烯炔。将两个乙炔分子掺入产物中。乙炔锌对硫亚胺盐的亲核攻击可能首先发生，形成炔基S，N-乙缩醛，然后进行[1,3]重排，生成3-亚磺基-1-氨基丙烯。
• Copper-Catalyzed Coupling Reaction of C−OMe Bonds Adjacent to a Nitrogen Atom with Terminal Alkynes
  作者：Bangben Yao、Yuhong Zhang、Yong Li

  DOI：10.1021/jo1007898

  日期：2010.7.2

  The cross coupling of the C-OMe bond adjacent to a nitrogen atom in dialkoxy-N,N-dialkylmethanamines with terminal alkynes was efficiently approached in the presence of copper catalyst under mild conditions to give 3-amino-1,4-diynes in good yields. The reaction is promoted by phosphine ligands and the chemistry provides a simple and efficient route to 3-amino-1,4-diynes. Importantly, the Michael addition occurred with as-prepared 3-amino-1,4-diynes to give the useful Michael-adducts containing tert-alkylamines in a very convenient way. Further studies revealed that (E)-1,5-diarylpent-1-en-4-yn-3-one was formed through the rearrangement by using the neutral alumina column, and the corresponding imine 2-(1,5-diphenylpent-2-en-4-ynylideneamino)ethanol was obtained in the presence of AgOTf.
• Synthesis of<i>N</i>,<i>N</i>-Disubstituted 3-Amino-1,4-diynes and 3-Amino-1-ynes by Addition of Alkynyldimethylaluminum Reagents to<i>N</i>,<i>N</i>-Disubstituted Formamides and N,O-Acetals
  作者：Balaji L. Korbad、Sang-Hyeup Lee

  DOI：10.1002/ejoc.201402464

  日期：2014.8

  A range of alkynyldimethylaluminum reagents were added to N,N‐disubstituted formamides and the their acetals to provide the corresponding N,N‐disubstituted 3‐amino‐1,4‐diynes. Also, these reagents smoothly underwent the addition to N,O‐acetals to give the corresponding N,N‐disubstituted 3‐amino‐1‐ynes.

  将一系列炔基二甲基铝试剂添加到N，N-二取代的甲酰胺及其缩醛中，以提供相应的N，N-二取代的3-氨基-1,4-二炔。同样，这些试剂平稳地添加到N，O-乙缩醛中，得到相应的N，N-二取代的3-amino-1-ynes。