1,4-bis(p-propionamidophenyl)butadiyne | 847900-39-4

• 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: 1,4-bis(p-propionamidophenyl)butadiyne
• 英文别名: N-[4-[4-[4-(propanoylamino)phenyl]buta-1,3-diynyl]phenyl]propanamide
• CAS: 847900-39-4
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: VKYGMWKMOOGORM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-乙炔基苯胺 在 copper diacetate 作用下， 以 吡啶 为溶剂， 生成 1,4-bis(p-propionamidophenyl)butadiyne
  参考文献：
  名称：

  Schizophyllan Can Act as a One-dimensional Host to Construct Poly(diacetylene) Nanofibers

  摘要：

  裂褶菌素与1,4-双(对氨基苯基)丁炔结合，并作为一维载体，通过紫外线照射产生纤维状聚二亚乙基聚合体。

  DOI：

  10.1246/cl.2005.40

文献信息

• Schizophyllan Can Act as a One-dimensional Host to Construct Poly(diacetylene) Nanofibers
  作者：Teruaki Hasegawa、Shuichi Haraguchi、Munenori Numata、Tomohisa Fujisawa、Chun Li、Kenji Kaneko、Kazuo Sakurai、Seiji Shinkai

  DOI：10.1246/cl.2005.40

  日期：2005.1

  Schizophyllan binds 1,4-bis(p-amidophenyl)butadiyne and acts as a one-dimensional host to produce fibrous polydiacetylene assemblies through UV-irradiation.

  裂褶菌素与1,4-双(对氨基苯基)丁炔结合，并作为一维载体，通过紫外线照射产生纤维状聚二亚乙基聚合体。
• Poly(diacetylene)-nanofibers can be fabricated through photo-irradiation using natural polysaccharide schizophyllan as a one-dimensional mold
  作者：Teruaki Hasegawa、Shuichi Haraguchi、Munenori Numata、Chun Li、Ah-Hyun Bae、Tomohisa Fujisawa、Kenji Kaneko、Kazuo Sakurai、Seiji Shinkai

  DOI：10.1039/b510646j

  日期：——

  Schizophyllan interacts with various 1,4-diphenylbutadiyne derivatives to induce their chirally-twisted packing. A series of referential experiments using other polysaccharides (amylose, pullulan, dextran, etc.) and a carbohydrate-appended detergent (dodecyl-β-D-glucopyranoside) indicates that these 1,4-diphenylbutadiyne derivatives are accommodated within a tubular cavity constructed by a helical superstructure of schizophyllan. In these 1,4-diphenylbutadiyne derivatives, 1,4-bis(p-propionamidophenyl)butadiyne can be easily polymerized through UV-irradiation, in which schizophyllan acts as a one-dimensional mold to produce the corresponding poly(diacetylene)s with fibrous morphologies. Detailed investigations on this unique approach to prepare the nanofibers revealed that it includes two individual processes, that is, 1) UV-mediated polymerization of encapsulated 1,4-bis(p-propionamidophenyl)butadiyne to produce immature nanofibers and 2) their reorganization through hydrophobic interfiber interactions into ordered nanofibers. The other 1,4-diphenylbutadiyne derivatives could not be polymerized through UV-irradiation, indicating that the p-propionamido-functionalities play substantial roles for a suitable packing of the monomer for the polymerization. The other 1,4-diphenylbutadiyne derivatives, however, can be also polymerized through γ-ray irradiation in the presence of schizophyllan to give the corresponding poly(diacetylene)-nanofibers, emphasizing the wide applicability of the schizophyllan-based strategy for polymerization of various 1,4-diphenylbutadiyne derivatives.

  水苏碱与各种 1,4-二苯基丁二炔衍生物相互作用，诱导它们的手性扭曲包装。使用其他多糖（直链淀粉、聚戊聚糖、葡聚糖等）和碳水化合物添加的去垢剂（十二烷基-β-D-吡喃葡萄糖苷）进行的一系列参照实验表明，这些 1,4-二苯基丁二炔衍生物被容纳在由螺旋形上部结构的五味子叶兰构建的管状空腔中。在这些 1,4-二苯基丁二炔衍生物中，1,4-双（对丙酰氨基苯基）丁二炔可以通过紫外线照射轻松聚合，其中五味子叶兰充当了一维模具，生产出相应的具有纤维状形态的聚（二乙炔）。对这种制备纳米纤维的独特方法进行的详细研究表明，它包括两个独立的过程，即：1）紫外线介导的封装 1,4-双（对丙酰氨基苯基）丁二炔聚合，生成未成熟的纳米纤维；2）通过疏水性纤维间相互作用使其重组为有序的纳米纤维。其他 1,4-二苯基丁二炔衍生物无法通过紫外线辐照聚合，这表明对丙酰胺基官能团对单体的适当聚合起着重要作用。然而，其他 1,4-二苯基丁二炔衍生物也可以在裂殖叶兰存在下通过γ射线辐照聚合，得到相应的聚（二乙炔）纳米纤维，这强调了基于裂殖叶兰的策略在聚合各种 1,4-二苯基丁二炔衍生物中的广泛适用性。