Buta-2,3-dien-anilid | 179242-29-6

• 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: Buta-2,3-dien-anilid
• 英文别名: N-phenylbuta-2,3-dienamide
• CAS: 179242-29-6
• 化学式: C₁₀H₉NO
• 分子量: 159.188
• InChiKey: VJYZRROBNSZLDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  对甲氧基苯异氰酸酯 、 Buta-2,3-dien-anilid 以 xylene 为溶剂， 反应 8.0h， 以26%的产率得到N-<(4-Methoxyphenyl)carbamoyl>-4-methyl-2-chinolon
  参考文献：
  名称：

  Cycloadditionen. 24. Synthese und Reaktionen vonsec. N-Aryl-buta-2,3-dien-amiden

  摘要：

  The reaction of aryl isocyanates (1) with allenyl magnesium bromide(2) furnishes the sec. N-aryl-3-butynamides (4), which tend to tautomerize to the 2,3-butadienamides (5). Further heating of 5a-f (bearing benzoid nuclei) leads to decompositon, only 5g (bearing the naphthyl group) undergoes the expected intramolecular Diels-Alder (IMDA) reaction, leading to the benzo-tricycle (7g). By reaction of a second molecule isocyanate 1 the carbamoylation of the NH moiety of 5a, c and of 3g and 4g, resp. takes place. The thereby formed N-aryl-N-butadienoyl ureas (9) either cyclize to furnish the the N-carbamoyl-2-quinolones (10) or undergo the IMDA-reaction leading to the tricyclic compounds (11). The N-butadienoyl-N-(1-naphthyl)ureas (12) only furnish the IMDA-benzo-tricycles (13).

  DOI：

  10.1002/prac.19963380169
• 作为产物：
  描述：

  N-phenylbut-3-ynamide 以 xylene 为溶剂， 反应 3.0h， 以79%的产率得到Buta-2,3-dien-anilid
  参考文献：
  名称：

  Cycloadditionen. 24. Synthese und Reaktionen vonsec. N-Aryl-buta-2,3-dien-amiden

  摘要：

  The reaction of aryl isocyanates (1) with allenyl magnesium bromide(2) furnishes the sec. N-aryl-3-butynamides (4), which tend to tautomerize to the 2,3-butadienamides (5). Further heating of 5a-f (bearing benzoid nuclei) leads to decompositon, only 5g (bearing the naphthyl group) undergoes the expected intramolecular Diels-Alder (IMDA) reaction, leading to the benzo-tricycle (7g). By reaction of a second molecule isocyanate 1 the carbamoylation of the NH moiety of 5a, c and of 3g and 4g, resp. takes place. The thereby formed N-aryl-N-butadienoyl ureas (9) either cyclize to furnish the the N-carbamoyl-2-quinolones (10) or undergo the IMDA-reaction leading to the tricyclic compounds (11). The N-butadienoyl-N-(1-naphthyl)ureas (12) only furnish the IMDA-benzo-tricycles (13).

  DOI：

  10.1002/prac.19963380169

文献信息

• Synthesis of Exo- and Endocyclic Enamides Through Copper-Catalyzed Regioselective Intramolecular <i>N</i> -Halovinylation
  作者：Nicolas Gilbert、Simon Ricard、Jodrey Bergeron、Pierre Lambolez、Benoit Daoust

  DOI：10.1002/ejoc.202000137

  日期：2020.5.10

  copper‐catalyzed cross‐coupling of 1,2‐dihaloalkenes and amides leads to cyclic β‐haloenamides, which can participate in a second cross‐coupling reaction to efficiently synthesize highly functionalized cyclic enamides. The selectivity of the intramolecular coupling between exo‐ and endocyclic regioisomers is a crucial synthetic factor and can be influenced by the structure of the substrate and the reaction conditions

  1,2-二卤代烯烃与酰胺的分子内铜催化交叉偶联反应生成环状β-卤代烯酰胺，后者可参与第二次交叉偶联反应以有效合成高度官能化的环状酰胺。外环和内环区域异构体之间分子内偶联的选择性是至关重要的合成因素，并受底物结构和反应条件的影响。
• Synthesis of Vinylic Sulfones in Aqueous Media
  作者：Jeffrey Goh、Manikantha Maraswami、Teck-Peng Loh

  DOI：10.1021/acs.orglett.0c04257

  日期：2021.2.5

  A green method for the sulfination of allenic carbonyl compounds to access a wide variety of vinylic sulfones is developed. This reaction works in aqueous media under very mild conditions. This reaction is atom economic. A wide variety of vinylic sulfones could be obtained in moderate to excellent yields with wide functional group tolerance. The efficiency of this method is demonstrated in some reactions

  开发了一种绿色的方法，用于将烯丙基羰基化合物硫化以使用各种乙烯基砜。该反应在非常温和的条件下在水性介质中进行。该反应是原子经济的。可以以中等到优异的收率获得各种乙烯基砜，并且具有宽泛的官能团耐受性。该方法的效率在某些反应中得到了证明，其中所需的产物可以通过过滤分离。
• Preference of β-Lactam Formation in Cu(I)-Catalyzed Intramolecular Coupling of Amides with Vinyl Bromides
  作者：Qiwu Zhao、Chaozhong Li

  DOI：10.1021/ol801545a

  日期：2008.9.18

  A general and highly efficient synthesis of 4-alkylidene-2-azetidinones was achieved by the Cu(I)-catalyzed intramolecular C-N coupling of amides with vinyl bromides. This 4-exo ring closure was found to be fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo) of cyclization under copper catalysis. Tandem C-N bond formation was then successfully developed to allow the convenient generation

  通过酰胺与乙烯基溴的铜（I）催化的分子内CN偶联，可以实现4-亚烷基-2-氮杂环丁烷酮的一般高效合成。发现在铜催化下，这种4-exo闭环在根本上优于环化的其他模式（5-exo，6-exo和6-endo）。然后成功开发了串联CN键，从而可以方便地生成中等大小的内酰胺。
• A Direct Synthesis of Substituted α - Allenic Carboxanilides from Allenyllithium Reagents
  作者：P. Audin、G. Drut-Grevoz、J. Paris

  DOI：10.1080/00397919308018591

  日期：1993.4

  Abstract The metalation of various allenic hydrocarbons and the subsequent reaction of the lithioderivatives with phenyl isocyanates as a synthetic route to α - allenyl carboxanilides is described. The best results were obtained with 3,3-disubstituted propadiene and 3,3,1-trisubstituted propadiene.

  摘要 描述了各种丙二烯烃的金属化以及锂硫衍生物与异氰酸苯酯的后续反应，作为合成 α-丙二烯基羧酰苯胺的途径。使用 3,3-二取代丙二烯和 3,3,1-三取代丙二烯获得最佳结果。