4-Chlor-N, N-diethyl-zimtsaeureamid | 123827-90-7

• 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: 4-Chlor-N, N-diethyl-zimtsaeureamid
• 英文别名: 3-(4-chlorophenyl)-N,N-diethylprop-2-enamide；(E)-3-(4-chlorophenyl)-N,N-diethylprop-2-enamide
• CAS: 123827-90-7
• 化学式: C₁₃H₁₆ClNO
• mdl: MFCD00705401
• 分子量: 237.729
• InChiKey: WBPWCIRTQWZMBD-JXMROGBWSA-N

物化性质

• 沸点：
  395.4±25.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 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,N-二乙基-2-丙烯酰胺 以87%的产率得到
  参考文献：
  名称：

  Du Jing-Xing, Huang Xian, Gaogeng xuexiao huaxun xiebao (Chen. J. Chin. Univ.), 15 (1994) N 10, S 1+

  摘要：

  DOI：

文献信息

• Stereoselective Olefination Reactions Promoted by Rieke Manganese
  作者：José Concellón、Humberto Rodríguez-Solla、Vicente del Amo、Pamela Díaz

  DOI：10.1055/s-0029-1216880

  日期：2009.8

  applied to develop a novel and direct synthesis of (E)-α,β-unsaturated esters or amides and (Z)-α,β-unsaturated α-halo esters and α-choroamides through a Mn*-mediated sequential olefination protocol of aldehydes with dichloro esters or amides and trihalo esters or trichloroamides, respectively. manganese - elimination reactions - stereoselectivity - α,β-unsaturated esters - α,β-unsaturated amides - metalation

  提出了使用廉价的无毒金属锰进行立体选择性β-消除反应并促进醛的顺序烯化反应以获得α，β-不饱和酯和酰胺的优势的研究。使用活性锰（Mn *）作为金属化剂进行了各种消除反应，所有这些反应均具有完全的立体选择性和高收率的特征。锰的这种能力已被用于开发通过Mn *-直接合成（E）-α，β-不饱和酯或酰胺与（Z）-α，β-不饱和α-卤代酯和α-氯酰胺的新颖而直接的合成方法。介导的醛分别与二氯酯或酰胺和三卤代酯或三氯酰胺的顺序烯烃化方案。 锰-消除反应-立体选择性-α，β-不饱和酯-α，β-不饱和酰胺-金属化
• Studies of the use of elemento-organic compounds of the fifteenth and sixteenth groups in organic synthesis LXXI. Reaction of α-halogeno carboxylic derivatives with carbonyl compounds promoted by tributylstibine
  作者：Yao-Zeng Huang、Chen Chen、Yanchang Shen

  DOI：10.1016/0022-328x(89)87318-8

  日期：1989.4

  α,β-Unsaturated esters and amides were conveniently obtained from the trialkylstibine-promoted reaction of α-halogenocarboxylic derivatives with carbonyl compounds. In this reaction, a quaternary stibonium salt is an active intermediate that can be trapped and can undergo further reaction with the substrate.

  从α-卤代羧酸衍生物与羰基化合物的三烷基苯乙烯促进的反应中方便地获得α，β-不饱和酯和酰胺。在该反应中，季sti盐是一种活性中间体，可以被捕获并与底物进行进一步反应。
• 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。