N,N'-[(4-nitrophenyl)methylene]bisacrylamide | 1422278-86-1

• 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: N,N'-[(4-nitrophenyl)methylene]bisacrylamide
• 英文别名: N,N'-(4-nitrophenylmethylene)diacrylamide；N-[(4-nitrophenyl)-(prop-2-enoylamino)methyl]prop-2-enamide
• CAS: 1422278-86-1
• 化学式: C₁₃H₁₃N₃O₄
• 分子量: 275.264
• InChiKey: KSOHVDFIKCYTEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 丙烯酰胺 在 N,N,N',N'-tetramethylethylene-diaminium-N,N'-disulfonic acid trifluoroacetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 以91%的产率得到N,N'-[(4-nitrophenyl)methylene]bisacrylamide
  参考文献：
  名称：

  N,N,N′,N′-Tetramethylethylene-diaminium-N,N′-disulfonic acid trifluoroacetate and pyridinium-N-sulfonic acid hydrogen sulfate as highly effective dual-functional catalysts for the preparation of N,N′-alkylidene bisamides

  摘要：

  在这项研究中，Brønsted酸性离子液体N,N,N′,N′-四甲基乙二胺-N,N′-二磺酸三氟乙酸酯([TMEDSA][TFA]2)和吡啶-N-磺酸氢硫酸盐([Py-SO3H][HSO4])被引入作为双功能催化剂，用于在无溶剂条件下通过一次酰胺(2当量)与芳基醛(1当量)的反应绿色、简单和有效地制备N,N′-烷基亚胺。与先前报道的催化剂相比，这些催化剂的反应结果和条件进行了比较。[TMEDSA][TFA]2和[Py-SO3H][HSO4]在反应时间(10-45分钟)、产率(86-98%)、温度和反应条件等两个或更多因素方面优于先前报道的催化剂。此外，提出了基于催化剂双重功能性的可能且有吸引力的机制。

  DOI：

  10.1515/znb-2019-0064

文献信息

• Molybdate and silica sulfuric acids as heterogeneous alternatives for synthesis of gem-bisamides and bisurides from aldehydes and amides, carbamates, nitriles or urea
  作者：Fatemeh Tamaddon、Hossein Kargar-Shooroki、Abbas Ali Jafari

  DOI：10.1016/j.molcata.2012.12.002

  日期：2013.3

  Molybdate sulfuric acid (MSA) and silica sulfuric acid (SSA) has been prepared and used as efficient solid catalysts for the synthesis of gem-bisamides and bisurides via the one-pot three-component reaction of two moles of amides, nitriles, carbamates or urea with aldehydes. The catalytic efficiency of SSA, MSA, or H2SO4 98% per H+ sites as turnover number (TON), turnover frequency (TOF), and atomic economy (AE) was calculated and compared for quantitative evaluation of catalysts. The AE, TON, and TOF factors show the superiority of the SSA versus MSA and H2SO4. Short reaction times, simple work-up, chemoselectivity, low loading, and reusability of solid acid catalysts are extra advantages than current methods reported in the literature with corrosive acidic catalysts. (C) 2012 Elsevier B.V. All rights reserved.
• Synthesis and Cytotoxic Activity of N,N′-(Arylmethylene)bisamides
  作者：Junichi Uenishi、Tatsuhiro Yoshiki、Hirokazu Hirano、Tsuyoshi Ueda、Naoyuki Hoshiya、Hiromi Ii

  DOI：10.1055/s-0034-1380437

  日期：——

  N,N'-(Arylmethylene) bisamides were prepared by an acidcatalyzed reaction of arylaldehydes with cinnamamide or acrylamides. The reaction was carried out in refluxing toluene for a few hours, and simple collection of the precipitate gave the desired products. The bisamides were designed as cytotoxic molecules based on the structure of the potently cytotoxic marine natural product (-)-zampanolide. The activities of the bisamides against two cancer cell lines were evaluated, and several compounds were found to show medium potency with IC50 values in the lower micromolar level.