3,3-diphenylpropanoic acid N,N-diisopropylamide

• 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-diisopropylamide
• 英文别名: 3,3-diphenyl-N,N-di(propan-2-yl)propanamide
• 化学式: C₂₁H₂₇NO
• 分子量: 309.451
• InChiKey: BQNPGXWRASVDKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-diphenylpropanoic acid N,N-diisopropylamide 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以61%的产率得到地索普明
  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：

  肉桂酸 在 氯化亚砜 、 aluminum tri-bromide 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-diisopropylamide
  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

• 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.
• 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.