(E)-N,N-diethyl-2,3-diphenylacrylamide | 78956-17-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-N,N-diethyl-2,3-diphenylacrylamide
• 英文别名: Cinnamamide, N,N-diethyl-2-phenyl-；(E)-N,N-diethyl-2,3-diphenylprop-2-enamide
• CAS: 78956-17-9
• 化学式: C₁₉H₂₁NO
• 分子量: 279.382
• InChiKey: PXRBGPWDWAAXCD-OBGWFSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N,N-diethyl-2,3-diphenylacrylamide 、 S-(三氟甲基)二苯并噻吩三氟甲基磺酸盐 在 N-甲基甲酰胺 、 copper(l) iodide 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 16.0h， 以11%的产率得到(Z)-N,N-diethyl-4,4,4-trifluoro-2,3-diphenylbut-2-enamide
  参考文献：
  名称：

  Regio- and Diastereoselective Cu-Mediated Trifluoromethylation of Functionalized Alkenes

  摘要：

  alpha- and beta-substituted N,N-diethylacrylamides undergo copper-mediated direct beta-trifluoromethylation. The amide moiety acts as a directing group for the regio- and the stereo-controlled introduction of the trifluoromethyl group. The reaction is carried out under acidic conditions in the presence of Umemoto's reagent. This method does not require prefunctionalized substrates and delivers excellent stereoselectivity.

  DOI：

  10.1021/jo402385g
• 作为产物：
  描述：

  苯可丁酸乙酸酯 、 三乙胺 在 三(2-呋喃基)膦 、 palladium diacetate 、 三甲基乙酸酐 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以77%的产率得到(E)-N,N-diethyl-2,3-diphenylacrylamide
  参考文献：
  名称：

  羧酸催化钯催化叔胺的N-酰化：合成酰胺的方法。

  摘要：

  通过C–N裂解，实现了羧酸对钯催化的叔胺的N-酰化反应。该反应显示出较宽的底物范围。芳族和脂族酸都很好地用作酰化剂，并与叔胺偶联以良好或优异的产率产生相应的酰胺。通过该策略，还可以有效地修饰生物活性羧酸，从而突出了该方法在有机合成中的合成价值。

  DOI：

  10.1021/acs.orglett.0c01869

文献信息

• Palladium-Catalyzed Hydroaminocarbonylation of Alkynes with Tertiary Amines via C–N Bond Cleavage
  作者：Bao Gao、Hanmin Huang

  DOI：10.1021/acs.orglett.7b03331

  日期：2017.11.17

  An efficient strategy for the cleavage of the C–N bond of tertiary amines was developed with DTBP as an oxidant, in which the cleaved H atom and amine moiety were successfully transferred to the desired products. This strategy has enabled an efficient palladium-catalyzed hydroaminocarbonylation of alkynes with tertiary amines. Notably, the catalyst loading could be lowered from 5 to 0.1 mol %, which

  以DTBP为氧化剂，开发了一种有效的叔胺C–N键断裂的策略，其中已断裂的H原子和胺部分已成功转移到所需的产物中。该策略已使炔烃与叔胺有效地进行钯催化的氢氨基羰基化。值得注意的是，催化剂的负载量可以从5 mol％降低到0.1 mol％，这代表了在报告的通过C–N键活化进行羰基化的最低催化剂负载量。
• New Convenient One-Pot Methods of Conversion of Alkynes to Cyclobutenediones or α,β-Unsaturated Carboxylic Acids Using Novel Reactive Iron Carbonyl Reagents
  作者：Mariappan Periasamy、Chellappan Rameshkumar、Ukkiramapandian Radhakrishnan、Jean-Jacques Brunet

  DOI：10.1021/jo971929d

  日期：1998.7.1

  Reactions of NaHFe(CO)(4)/RX or [HFe3(CO)(11)](-) reagents with alkynes lead to the formation of the corresponding cr,P-unsaturated carboxylic acids and/or the cyclobutenediones. The reagent; generated in situ using the NaHFe(CO)(4)/CH3I combination in THF, on reaction with alkynes followed by CuCl2. 2H(2)O oxidation, gives the corresponding cyclobutenediones (27-42%) and alpha,beta-unsaturated carboxylic acids (10-22%), whereas the reagent generated using CH2Cl2 in place of CH3I leads to a,P-unsaturated carboxylic acids (37-60%) and their derivatives (35-55%) at 25 degrees C. The same reagent system in the presence of acetic acid (4 equiv) yields the corresponding cyclobutenedione (33%). The reaction using Me3SiCl gives the corresponding alpha,beta-unsaturated carboxylic acids (45-54%) at 25 degrees C and the corresponding cyclobutenediones (51-63%) at 60 degrees C. Interestingly, the reaction of the [HFe3(CO)(11)](-) species generated using Fe(CO)(5)/NaBH4/CH3COOH, with alkynes at 25 degrees C, followed by CuCl2. 2H(2)O oxidation gives the corresponding cyclobutenediones (60-73%). The possible intermediates and pathways for the formation of alpha,beta-unsaturated carboxylic acids and cyclobutenediones are discussed.
• A new method for the regio and stereoselective hydrocarboxylation of alkynes using NaHFe(CO)4CH2Cl2 system
  作者：Mariappan Periasamy、Ukkiramapandian Radhakrishnan、Chellappan Rameshkumar、Jean-Jacques Brunet

  DOI：10.1016/s0040-4039(97)00104-4

  日期：1997.3

  The reagent generated in situ in THF using NaHFe(CO)(4) and CH2Cl2 was used for the regio and stereoselective hydrocarboxylation of terminal and internal alkynes to obtain alpha,beta-unsaturated carboxylic acid derivatives. (C) 1997 Published by Elsevier Science Ltd.
• Eicher, Theophil; Boehm, Siegfried; Ehrhardt, Heinz, Liebigs Annalen der Chemie, 1981, # 5, p. 765 - 788
  作者：Eicher, Theophil、Boehm, Siegfried、Ehrhardt, Heinz、Harth, Robert、Lerch, Dieter

  DOI：——

  日期：——
• The Analgesic Activity of N,N-Dialkyl Amides¹
  作者：Domenick Papa、Erwin Schwenk、Frank Villani、Erwin Klingsberg

  DOI：10.1021/ja01165a016

  日期：1950.9