N-(buta-2,3-dienyl)furan-2-carboxamide | 1310558-71-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(buta-2,3-dienyl)furan-2-carboxamide
• 英文别名: N-(buta-2,3-dien-1-yl)-2-furamide
• CAS: 1310558-71-4
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: BEIMPUOCWQRSHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(buta-2,3-dienyl)furan-2-carboxamide 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以65%的产率得到5-(1-bromovinyl)-2-(furan-2-yl)-4,5-dihydrooxazole
  参考文献：
  名称：

  N-溴代琥珀酰亚胺对N-（Buta-2,3-二烯基）酰胺的亲电环化反应及其应用研究

  摘要：

  AbstractAn efficient protocol for the synthesis of oxazoline and bisoxazoline derivatives via electrophilic cyclization of N‐(buta‐2,3‐dienyl)amides with N‐bromosuccinimide (NBS) at room temperature has been developed. Synthetic transformations of the obtained oxazolines have been successfully performed due to the presence of vinyl bromide units comprising an elimination reaction and a copper(I)‐catalyzed CN coupling reaction using diethylamine (Et2NH) as the ligand.magnified image

  DOI：

  10.1002/adsc.201300959
• 作为产物：
  描述：

  聚合甲醛 、 N-(prop-2-yn-1-yl)furan-2-carboxamide 在 copper(l) iodide 、 二环己胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以72%的产率得到N-(buta-2,3-dienyl)furan-2-carboxamide
  参考文献：
  名称：

  由末端N-炔丙基酰胺 有效合成N-（buta-2,3- dienyl）酰胺及其对恶唑啉衍生物的合成潜力†

  摘要：

  一系列Ñ -allenyl酰胺被方便地从制备Ñ -propargyl以良好至优异的产率的酰胺通过该组中开发了一种改进的方法。已经开发了在有机碘化物存在下这些制备的N-烯丙基酰胺的钯催化偶联-环化反应，从而有效地提供了恶唑啉衍生物。

  DOI：

  10.1039/c2ob26291f

文献信息

• Efficient synthesis of N-(buta-2,3-dienyl) amides from terminal N-propargyl amides and their synthetic potential towards oxazoline derivatives
  作者：Bo Chen、Nan Wang、Wu Fan、Shengming Ma

  DOI：10.1039/c2ob26291f

  日期：——

  A series of N-allenyl amides was prepared conveniently from N-propargyl amides in good to excellent yields via a modified procedure developed in this group. The palladium-catalyzed coupling–cyclization of these prepared N-allenyl amides in the presence of organic iodides has been developed affording the oxazoline derivatives efficiently.

  一系列Ñ -allenyl酰胺被方便地从制备Ñ -propargyl以良好至优异的产率的酰胺通过该组中开发了一种改进的方法。已经开发了在有机碘化物存在下这些制备的N-烯丙基酰胺的钯催化偶联-环化反应，从而有效地提供了恶唑啉衍生物。
• Gold Catalysis: 1,3-Oxazines by Cyclisation of Allene Amides
  作者：A. Stephen K. Hashmi、Andreas M. Schuster、Sebastian Litters、Frank Rominger、Markus Pernpointner

  DOI：10.1002/chem.201100132

  日期：2011.5.9

  A series of allene amides was prepared and their gold‐catalysed cyclisation was investigated. The formation of six‐membered rings, 1,3‐oxazines, was observed. Dihydropyrroles originating from intramolecular hydroamination of the distal CC double bonds of the allenes were minor side products. Mechanistic studies by in situ 31P NMR spectroscopy showed only one additional species during the conversion

  制备了一系列的烯丙基酰胺，并研究了它们在金催化下的环化反应。观察到六元环1,3-恶嗪的形成。源自亚丙基的远端CC双键的分子内加氢胺化的二氢吡咯是次要的副产物。通过原位31 P NMR光谱进行的机理研究表明，在每种情况下，转化过程中仅增加了一种。通过对不同烯丙基金（I）物种的计算研究，可以将其指定为在空间位阻较少的亚甲基末端带有金催化剂的σ-烯丙基金。该中间体的区域特异性氘化脱氢证实了催化循环最后一步的S E '型机制。
• Studies on Electrophilic Cyclization of<i>N</i>-(Buta-2,3-dienyl)amides with<i>N</i>-Bromosuccinimide and its Applications
  作者：Nan Wang、Bo Chen、Shengming Ma

  DOI：10.1002/adsc.201300959

  日期：2014.2.10

  AbstractAn efficient protocol for the synthesis of oxazoline and bisoxazoline derivatives via electrophilic cyclization of N‐(buta‐2,3‐dienyl)amides with N‐bromosuccinimide (NBS) at room temperature has been developed. Synthetic transformations of the obtained oxazolines have been successfully performed due to the presence of vinyl bromide units comprising an elimination reaction and a copper(I)‐catalyzed CN coupling reaction using diethylamine (Et2NH) as the ligand.magnified image
• CuI-Catalyzed Synthesis of Functionalized Terminal Allenes from 1-Alkynes
  作者：Hongwen Luo、Shengming Ma

  DOI：10.1002/ejoc.201201696

  日期：2013.5

  equiv.), a facile and efficient protocol for the gram-scale synthesis of functionalized terminal allenes by using CuI (7.5–10 mol-%), paraformaldehyde (1.6 equiv.), and diisopropylamine (1.4 equiv.) has been developed. This method accommodates different functional groups such as hydroxy or carbonyl, and it also performed well in the synthesis of allenylamides and 2,3-butadien-1-ol.

  相对于我们使用 CuI（0.5 当量）、多聚甲醛（2.5 当量）和二环己胺（1.8 当量）的原始方案，这是一种使用 CuI（7.5– 10 mol-%)、多聚甲醛（1.6 当量）和二异丙胺（1.4 当量）已被开发。该方法适应不同的官能团，如羟基或羰基，在合成丙二烯酰胺和2,3-丁二烯-1-醇方面也表现良好。