3-(4-methylphenyl)-3-phenylpropanoic acid N-methylamide

• 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-(4-methylphenyl)-3-phenylpropanoic acid N-methylamide
• 英文别名: N-methyl-3-(4-methylphenyl)-3-phenylpropanamide
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: VUDHELVLCMIHBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对甲基肉桂酸 在 氯化亚砜 、 氟磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 3-(4-methylphenyl)-3-phenylpropanoic acid N-methylamide
  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

• 10.1039/d4sc02821j
  作者：Lan, Liyuan、Xu, Kun、Zeng, Chengchu

  DOI：10.1039/d4sc02821j

  日期：——

  The reductive activation of chemical bonds at less negative potentials provides a foundation for high functional group tolerance and selectivity, and it is one of the central topics in organic electrosynthesis. Along this line, we report the design of a dual-activation mode by merging electro-reduction with hydrogen bonding activation. As a proof of principle, the reduction potential of N-phenylpropiolamide

  在较低负电势下化学键的还原活化为高官能团耐受性和选择性奠定了基础，是有机电合成的中心主题之一。沿着这条线，我们报告了通过将电还原与氢键激活相结合的双激活模式的设计。作为原理证明， N-苯基丙酰胺的还原电位正移了 218 mV。通过该策略，无需外部自由基前体和预官能化步骤即可完成N-芳基丙酰胺的自由基 Smiles 重排。 [DBU][HOAc]是一种易于获得的离子液体，首次被用作氢键供体和支持电解质。
• 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.