3,3-diphenylpropanoic acid N,N-diethylamide | 80467-87-4

• 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: 3,3-diphenylpropanoic acid N,N-diethylamide
• 英文别名: N,N-diethyl-3,3-diphenylpropionamide；N,N-diethyldiphenylpropionamide；3,3-diphenyl-propionic acid diethylamide；β.β-Diphenyl-propionsaeure-diaethylamid；3,3-Diphenyl-propionsaeure-diaethylamid；N,N-diethyl-3,3-diphenylpropanamide
• CAS: 80467-87-4
• 化学式: C₁₉H₂₃NO
• 分子量: 281.398
• InChiKey: VRZRWCJJLSGPDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  肉桂酰氯 在 三氟甲磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.17h， 生成 3,3-diphenylpropanoic acid N,N-diethylamide
  参考文献：
  名称：

  Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals

  摘要：

  Cinnamides ArCH=CHCONRR' in reactions with arenes Ar'H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give C=C bond hydroarylation products ArAr'CHCH2CONRR' in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr'CHCH2CH2NRR', valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR', have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.11.033

文献信息

• Superacidic Activation ofα,β-Unsaturated Amides and Their Electrophilic Reactions
  作者：Konstantin Yu. Koltunov、Stéphane Walspurger、Jean Sommer

  DOI：10.1002/ejoc.200400313

  日期：2004.10

  The electrophilic reactivity of α,β-unsaturated amides towards weak nucleophiles such as arenes and cyclohexane, initiated either with triflic acid (CF3SO3H) or with excess AlCl3, has been studied. The amides generally condense readily with aromatics in the presence of AlCl3 to give 3-arylpropionamides and related compounds in excellent yields, while some amides also undergo selective ionic hydrogenation

  已经研究了用三氟甲磺酸 (CF3SO3H) 或过量 AlCl3 引发的 α,β-不饱和酰胺对弱亲核试剂如芳烃和环己烷的亲电反应性。在 存在下，酰胺通常很容易与芳烃缩合，以极好的收率得到 3-芳基丙酰胺和相关化合物，而一些酰胺也可以与环己烷进行选择性离子氢化，得到饱和酰胺。这些反应的拟议机制涉及双阳离子中间体（超亲电试剂）。报告了对双阳离子物质的直接观察（通过低温 NMR）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Superelectrophilic activation of polyfunctional organic compounds using zeolites and other solid acidsElectronic supplementary information (ESI) available: experimental details, including activation of solid acids and typical procedure. See http://www.rsc.org/suppdata/cc/b4/b404074k/
  作者：Konstantin Yu. Koltunov、St�phane Walspurger、Jean Sommer

  DOI：10.1039/b404074k

  日期：——

  Zeolites and other available solid acids have been successfully applied to initiate reactions, which were earlier recognised to involve superelectrophilic intermediates and thus required excess of superacids to be carried out.

  沸石和其他可用的固体酸已被成功用于引发反应，这些反应早先被认为涉及超亲电性中间体，因此需要过量的超酸才能进行。
• Hautpflegemittel
  申请人：Henkel Kommanditgesellschaft auf Aktien

  公开号：EP0039857A1

  公开（公告）日：1981-11-18

  Die Mittel enthalten 0,5 bis 30 (3 bis 15) Gewichtsprozent an arylsubstituierten Alkansäurederivaten der allgemeinen Formel (I) als Inhibitor für bakterielle Lipase- und Esteraseenzyme, um Spaltungsreaktionen von Hauttriglyceriden mit Fettsäurefreisetzung zu verhindern. Solche Fettsäuren können Ursache für Hautausschläge sein. Ar = gegebenenfalls substituierter Arylrest X = Sauerstoff oder Schwefel R1 = H, Alkyl-(C1-4) oder ggf. substituierter Phenylrest R2 = H oder-OH R3, R4 = unabhängig voneinander H oder Alkyl-(C1-4) R5 = Alkoxy-(C1-10), -NH2, Mono- oder Dialkylaminogruppe p = 0 oder 1, m = 1 oder 2, n = 0, 1 oder 2 Die Alkansäurederivate können auch als Wirkstoffe in Deodorantien verwendet werden.

  组合物中含有 0.5%至 30%（3%至 15%）（按重量计）的通式（I）芳基取代的烷酸衍生物，作为细菌脂肪酶和酯酶的抑制剂，以防止皮肤甘油三酯的裂解反应和脂肪酸的释放。此类脂肪酸可能是引起皮疹的原因。 Ar = 任选取代的芳基 X = 氧或硫 R1 = H、烷基（C1-4）或可能取代的苯基残基 R2 = H 或-OH R3、R4 = 独立的 H 或烷基-(C1-4) R5 = 烷氧基-（C1-10）、-NH2、单烷基或二烷基氨基 p = 0 或 1，m = 1 或 2，n = 0、1 或 2 烷酸衍生物还可用作除臭剂的活性成分。
• One-pot tandem hydrophenylation and ionic hydrogenation of 3-phenylpropynoic acid derivatives under superelectrophilic activation
  作者：Denis I. Nilov、Aleksander V. Vasilyev

  DOI：10.1016/j.tetlet.2015.09.026

  日期：2015.10

  The reactions of esters and amides of 3-phenylpropynoic acid with strong Lewis acids AIX(3) (X = Cl, Br) or conjugate Bronsted-Lewis superacids HX-AIX(3) (X = Cl, Br) in benzene and cyclohexane at room temperature afforded 3,3-diphenylpropanoic acid derivatives in up to 94% yield. This tandem reaction of the acetylene bond proceeded by hydrophenylation followed by ionic hydrogenation. (C) 2015 Published by Elsevier Ltd.
• Friedel–Crafts alkylation of benzene with α,β-unsaturated amides
  作者：Konstantin Yu. Koltunov、Stéphane Walspurger、Jean Sommer

  DOI：10.1016/j.tetlet.2004.03.067

  日期：2004.4

  A variety of alpha, beta-unsaturated amides (RHC=CH2CONR'(2), R = H, Me, Ar; R'= H or Et) readily condense with benzene at room temperature in the presence of an excess of aluminum chloride to give the corresponding 3-phenylpropionamides in excellent yields. This simple, one-pot procedure proved to be efficient and very clean. The mechanism of these and related reactions is discussed and the participation of superelectrophilic dicationic intermediates is suggested. (C) 2004 Elsevier Ltd. All rights reserved.