(E)-N,N-diethyl-4-phenyl-3-butenamide | 103896-68-0

• 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: (E)-N,N-diethyl-4-phenyl-3-butenamide
• 英文别名: (E)-N,N-diethyl-4-phenylbut-3-enamide；N,N-Diethyl-4-phenyl-3-butenamide；3-Butenamide, N,N-diethyl-4-phenyl-, (E)-
• CAS: 103896-68-0
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: VVTKGYQJNGSWAY-DHZHZOJOSA-N

物化性质

• 沸点：
  354.2±31.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-[(E)-3-phenyl-2-propenyl]diethylamine 以70%的产率得到
  参考文献：
  名称：

  Murahashi Shun-Ichi, Imada Yasushi, Nishimura Koichi, Tetrahedron, 50 (1994) N 2, S 453-464

  摘要：

  DOI：

文献信息

• Visible Light Induced Brønsted Acid Assisted Pd‐Catalyzed Alkyl Heck Reaction of Diazo Compounds and <i>N</i> ‐Tosylhydrazones
  作者：Ziyan Zhang、Nikita Kvasovs、Anastasiia Dubrovina、Vladimir Gevorgyan

  DOI：10.1002/anie.202110924

  日期：2022.1.3

  mild visible light-induced palladium-catalyzed alkyl Heck reaction of diazo compounds and N-tosylhydrazones is reported. This method features Brønsted acid assisted generation of hybrid palladium C(sp3)-centered radical intermediate and broad reaction scope, highlighting the diverse applicability and the potential utility of this protocol in late-stage functionalization.

  报道了重氮化合物和N-甲苯磺酰腙的温和可见光诱导的钯催化烷基 Heck 反应。该方法具有布朗斯台德酸辅助生成杂化钯C(sp 3 )中心自由基中间体和广泛的反应范围，突出了该方案在后期功能化中的多样化适用性和潜在效用。
• Palladium-Catalyzed Aminocarbonylation of Cinnamyl<i>N</i>,<i>N</i>-Dialkylcarbamates. An Intriguing Crossover with<i>p</i>-Methylcinnamylamines
  作者：Masahiro Miyazawa、Keiji Yamamoto

  DOI：10.1246/cl.1994.491

  日期：1994.3

  Competition experiments in the palladium-catalyzed aminocarbonylation of cinnamyl N,N-dialkylcarbamates with p-methylcinnamylamines revealed that the allylamine did not undergo oxidative addition but attacked extensively a π-allylpalladium which arose from the allyl carbamate under the conditions employed, forming a mixture of the corresponding amides containing either cinnamyl moiety that incorporates a dialkylamino component originated only from the carbamate.

  在钯催化 N,N-二烷基氨基甲酸肉桂酯与对甲基肉桂胺的氨基羰基化过程中进行的竞争实验表明，烯丙基胺不会发生氧化加成，而是会在所采用的条件下广泛侵蚀由氨基甲酸烯丙酯产生的π-烯丙基钯，从而形成含有肉桂基的相应酰胺的混合物，其中包含仅由氨基甲酸烯丙酯产生的二烷基氨基成分。
• RHODIUM-CATALYZED AZACARBONYLATION OF ALLYL PHOSPHATES. THE PREPARATION OF β,γ-UNSATURATED AMIDES FROM ALLYL ALCOHOLS
  作者：Shun-Ichi Murahashi、Yasushi Imada

  DOI：10.1246/cl.1985.1477

  日期：1985.10.5

  Allyl phosphates undergo a smooth azacarbonylation reaction with amines to afford β,γ-unsaturated amides at 50 °C under CO atmosphere (20 atm) in the presence of Rh6(CO)16 catalyst and Bu4NCl co-catalyst.

  在 Rh6(CO)16 催化剂和 Bu4NCl 助催化剂的作用下，烯丙基磷酸盐与胺在 50 °C 的 CO 大气（20 个大气压）中顺利发生偶氮羰基化反应，生成 β,γ-不饱和酰胺。
• Aza- and oxacarbonylations of allyl phosphates catalyzed by rhodium carbonyl cluster. Selective synthesis of β, γ-unsaturated amides, esters, and acids
  作者：Yasushi Imada、Ou Shibata、Shun-Ichi Murahashi

  DOI：10.1016/0022-328x(93)83025-q

  日期：1993.6

  Rhodium-catalyzed carbonylation of allyl phosphates under CO (20 atm) at 50°C proceeds very efficiently in the presence of amines, alcohols, and water to give the corresponding β,γ-unsaturated amides, esters, and acids, respectively. These carbonylations occur with high regioselectivity at the less substituted carbon of allyl unit to give linear β,γ-unsaturated acid derivatives.

  在胺，醇和水的存在下，在50°C的CO（20 atm）下铑的烯丙基磷酸酯的羰基催化羰基化反应非常有效，分别得到相应的β，γ-不饱和酰胺，酯和酸。这些羰基化在烯丙基单元的较少取代的碳上以较高的区域选择性发生，从而得到线性的β，γ-不饱和酸衍生物。
• Palladium-catalyzed Carbonylation of Allylamines. Synthesis of β,γ-unsaturated amides by one-carbon homologation of Allylamines
  作者：Shun-Ichi Murahashi、Yasushi Imada、Koichi Nishimura

  DOI：10.1016/s0040-4020(01)80767-5

  日期：1994.1

  Palladium-catalyzed carbonylation of allylamines under CO (50atm) at 110°C proceeds highly efficiently to give the corresponding β,γ-unsaturated amides. The carbonylation occurs at the less substituted carbon of allyl units to give linear amides with high regioselectivity. The reaction can be rationalized by assuming the mechanism which involves oxidative addition of palladium (0) species to allylamines

  在110°C的CO（50atm）下钯烯丙基胺的羰基催化羰基化反应非常高效，得到相应的β，γ-不饱和酰胺。羰基化发生在烯丙基单元的较少取代的碳上，得到具有高区域选择性的线性酰胺。可以通过假设以下机理来使反应合理化：该机理涉及将钯（0）物种氧化添加到烯丙胺中以生成π-烯丙基钯络合物，插入一氧化碳以生成酰基戊烯物种和酰胺化。