3-(4-methylphenyl)-1-diethylamino-2-propen-1-one | 99564-71-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(4-methylphenyl)-1-diethylamino-2-propen-1-one
• 英文别名: (E)-N,N-diethyl-3-p-tolylacrylamide；4-methyl-trans-cinnamic acid diethylamide；4-Methyl-trans-zimtsaeure-diaethylamid；(E)-N,N-diethyl-3-(4-methylphenyl)prop-2-enamide
• CAS: 99564-71-3
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: UUWUZOWQKPANJO-ZHACJKMWSA-N

物化性质

• 沸点：
  377.2±21.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 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：

  4-methylcinnamic acid 在 氯化亚砜 、 二乙胺 作用下， 生成 3-(4-methylphenyl)-1-diethylamino-2-propen-1-one
  参考文献：
  名称：

  The Analgesic Activity of N,N-Dialkyl Amides¹

  摘要：

  DOI：

  10.1021/ja01165a016

文献信息

• (E)-α,β-unsaturated amides from tertiary amines, olefins and CO via Pd/Cu-catalyzed aerobic oxidative N-dealkylation
  作者：Renyi Shi、Hua Zhang、Lijun Lu、Pei Gan、Yuchen Sha、Heng Zhang、Qiang Liu、Matthias Beller、Aiwen Lei

  DOI：10.1039/c4cc08925a

  日期：——

  A novel Pd/Cu-catalyzed chemoselective aerobic oxidative N-dealkylation/carbonylation reaction has been developed. Tertiary amines are utilized as a "reservoir" of "active" secondary amines in this transformation, which inhibits the formation of undesired by-products and the deactivation of the catalysts. This protocol allows for an efficient and straightforward construction of synthetically useful

  新型的钯/铜催化化学选择性好氧氧化N-脱烷基/羰基化反应。在该转化中，叔胺被用作“活性”仲胺的“储库”，其抑制了不希望的副产物的形成和催化剂的失活。该协议允许从容易获得的叔胺，烯烃和一氧化碳高效，直接地构建合成有用的且具有生物活性的（E）-α，β-不饱和酰胺衍生物。
• Microwave-assisted one-pot synthesis of a, β-unsaturated amides under solvent-free conditions
  作者：Shilei Jiang、Yuanyuan Xie、Xiaochun Yu

  DOI：10.3184/030823409x393682

  日期：2009.1

  Under microwave-assisted solvent-free conditions a one-pot reaction of triphenylphosphine, an aldehyde and N, N-diethyl chloroacetamide in the presence of zinc dust affords α, β-unsaturated amides stereoselectively in good yield. In comparison with the conventional heating method, the reaction was finished within five minutes under microwave irradiation.

  在微波辅助的无溶剂条件下，三苯基膦、醛和 N, N-二乙基氯乙酰胺在锌粉存在下的一锅反应以良好的收率立体选择性地提供了 α, β-不饱和酰胺。与传统的加热方法相比，在微波照射下，反应在五分钟内完成。
• Indium-Mediated Microwave-Assisted One-Pot Synthesis of α,β-Unsaturated Amides
  作者：Sunlin Feng、Shilei Jiang、Zhiying Zhang、Xiaochun Yu

  DOI：10.3184/030823410x520750

  日期：2010.7

  A stereoselective synthesis of α,βunsaturated-N,N-diethyl amides was achieved by a one-pot reaction of triphenylphosphine, an aromatic aldehyde, and N,N-diethyl chloroacetamide in the presence of indium under microwave-assisted and solvent-free condition.

  通过三苯基膦、芳香醛和N,N-二乙基氯乙酰胺在微波辅助和无溶剂条件下，在铟存在下的一锅反应，实现了α,β不饱和-N,N-二乙基酰胺的立体选择性合成.
• A New One-Pot Synthesis of α,β-Unsaturated Amides
  作者：Jianhua Zheng、Zhibei Wang、Yanchang Shen

  DOI：10.1080/00397919208021635

  日期：1992.6

  Abstract A new one-pot synthesis of α,β-unsaturated amides with high stereoselectivity by the reaction of aldehydes with bromoacetamides promoted by tri-n-butylphosphine and zinc is described.

  摘要 描述了一种通过三正丁基膦和锌促进的醛与溴乙酰胺反应一锅法合成具有高立体选择性的α,β-不饱和酰胺的新方法。
• Synthesis of α,β-Unsaturated Amide via Phosphonium Ylide
  作者：Shilei Jiang、Kefeng Yang、Xiaochun Yu

  DOI：10.1080/00397910802590902

  日期：2009.4.22

  A series of ,-unsaturated amides were prepared by the Wittig reaction of N,N-diethylamidemethylenetriphenylphosphorane ylide with aldehydes with moderate to good yields.