3,3-diphenyl-1-piperidin-1-yl-propan-1-one

• 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-diphenyl-1-piperidin-1-yl-propan-1-one
• 英文别名: 3,3-Diphenyl-1-piperidin-1-ylpropan-1-one
• 化学式: C₂₀H₂₃NO
• 分子量: 293.409
• InChiKey: DKXJHTFYYVVGBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  3,3-diphenyl-1-piperidin-1-yl-propan-1-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以90%的产率得到芬哌丙烷
  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
• 作为产物：
  描述：

  哌啶 在 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 32.08h， 生成 3,3-diphenyl-1-piperidin-1-yl-propan-1-one
  参考文献：
  名称：

  通过光氧化还原生成的氨基甲酰基自由基制备无环 1,4-二羰基酰胺的 Umpolung 方法

  摘要：

  光氧化还原催化用于从草酸盐生成氨基甲酰基。添加到一系列缺电子烯烃中可获得高产率的 1,4-氨基-羰基产物。反应在温和条件下进行，可以使用过渡金属或有机光催化剂。

  DOI：

  10.1002/chem.202300403

文献信息

• 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.
• Dicationic Intermediates Involving Protonated Amides:  Dual Modes of Reactivity Including the Acylation of Arenes
  作者：Douglas A. Klumpp、Rendy、Yun Zhang、Alma Gomez、Aaron McElrea

  DOI：10.1021/ol049512z

  日期：2004.5.1

  In the Bronsted superacid CF3SO3H (triflic acid), amides are able to form reactive, dicationic electrophiles. It is shown that these dicationic intermediates participate in two distinctly different types of electrophilic reactions. The protonated amide increases the reactivity of an adjacent electrophilic group, and the protonated amide group itself shows enhanced reactivity arising from an adjacent cationic charge. In the latter case, several types of amides are even capable of reacting with benzene by Friedel-Crafts acylation.
• Tandem superelectrophilic hydroarylation of C C bond and carbonyl reduction in cinnamides: synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals
  作者：Dmitry N. Zakusilo、Dmitry S. Ryabukhin、Irina A. Boyarskaya、Oleg S. Yuzikhin、Aleksander V. Vasilyev

  DOI：10.1016/j.tet.2014.11.033

  日期：2015.1

  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.
• An Umpolung Approach to Acyclic 1,4‐Dicarbonyl Amides via Photoredox‐Generated Carbamoyl Radicals
  作者：Jason D. Williams、Stuart G. Leach、William J. Kerr

  DOI：10.1002/chem.202300403

  日期：——

  Photoredox catalysis is used to generate carbamoyl radicals from oxamate salts. Addition to a range of electron-poor olefins gives the 1,4-amido-carbonyl products in good yields. The reaction proceeds under mild conditions, and a transition metal or organic photocatalyst can be employed.

  光氧化还原催化用于从草酸盐生成氨基甲酰基。添加到一系列缺电子烯烃中可获得高产率的 1,4-氨基-羰基产物。反应在温和条件下进行，可以使用过渡金属或有机光催化剂。