(E)-3-benzylamino-1-phenylprop-2-en-1-one | 70008-82-1

• 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: (E)-3-benzylamino-1-phenylprop-2-en-1-one
• 英文别名: (E)-3-(benzylamino)-1-phenylprop-2-en-1-one
• CAS: 70008-82-1
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: IVRRMSTXQCAAKY-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (E)-3-benzylamino-1-phenylprop-2-en-1-one 、 苯胺 以 甲醇 为溶剂， 反应 29.0h， 以60%的产率得到(1-Benzyl-3-phenyl-2,4-dihydropyrimidin-5-yl)-phenylmethanone
  参考文献：
  名称：

  一种新型新取代的1,2,3,4-四氢嘧啶的简便一锅合成方法，第2部分†：1-（芳烷基/芳基）-3-（烷基/芳烷基/芳基）-5-芳酰基-1,2的合成，3,4-四氢嘧啶

  摘要：

  1-（芳烷基/芳基）-3-（烷基芳烷基）-5-芳酰基-1,2,3,4-四氢嘧啶（2a-c）是通过5-芳酰基-6-甲硫基1,2-的脱硫甲基化合成的， 3，4-四氢嘧啶（1a-c）。通过使烯胺酮3与主胺和甲醛在回流的甲醇中以良好的产率反应，已经开发了标题化合物2a-t的另一种单锅合成策略。

  DOI：

  10.1002/jhet.5570410425
• 作为产物：
  描述：

  苯乙酮 在 碘 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 60.0h， 生成 (E)-3-benzylamino-1-phenylprop-2-en-1-one
  参考文献：
  名称：

  烯胺酮和伯胺的电化学多组分[2+2+1]级联环化合成4-酰基咪唑

  摘要：

  烯胺酮和伯胺的电化学多组分[2+2+1]级联环化已被开发用于合成4-酰基咪唑。在未分裂的细胞中，烯胺酮和伯胺可以顺利地参与该反应，在室温下提供一系列1,2-二取代的4-酰基咪唑。该反应避免了使用过渡金属催化剂和氧化试剂，这使其更具可持续性和可再生性。

  DOI：

  10.1039/d3cc06196e

文献信息

• Acid-Catalyzed Cascade Reactions of Enaminones with Aldehydes: C-H Functionalization To Afford 1,4-Dihydropyridines
  作者：Jingyu Yang、Chengyu Wang、Xin Xie、Hongfeng Li、Yanzhong Li

  DOI：10.1002/ejoc.201000607

  日期：2010.8

  An efficient acid-catalyzed approach to the synthesis of functional 1,4-dihydropyridines from the reaction of readily available enaminones with aldehydes has been developed. This methodology was realized by a cascade reaction involving first formation of divinylmethanes and subsequent intramolecular cyclization.

  已开发出一种有效的酸催化方法，可通过容易获得的烯胺酮与醛的反应合成功能性 1,4-二氢吡啶。这种方法是通过级联反应实现的，包括首先形成二乙烯基甲烷和随后的分子内环化。
• Deuterium Isotope Effects on 13C Chemical Shifts of Enaminones.
  作者：Donka Kh. Zheglova、Daniel G. Genov、Simon Bolvig、Poul Erik Hansen、M. Hanfland、E. Dooryhee

  DOI：10.3891/acta.chem.scand.51-1016

  日期：——

  Deuterium isotope effects on C-13 chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, (2) Delta C-1(ND). Methyl-substitution al C-l leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between (2) Delta C-1(ND) and (3) Delta C-2'(ND). The latter becomes negative in the sterically hindered cases. (3) Delta C-2'(ND) may therefore be used as a gauge of the twist of the phenyl ring.o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller (2) Delta C-2(ND) and (2) Delta C-2 ''(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer (2) Delta C(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, (2) Delta C(OD), isotope effects.
• GRANIK, V. G.;ZHIDKOVA, A. M.;ZHIVOTOVSKAYA, I. S.;SOLOVEVA, N. P.;POLIEV+, ZH. ORGAN. XIMII, 1981, 17, N 11, 2421-2425
  作者：GRANIK, V. G.、ZHIDKOVA, A. M.、ZHIVOTOVSKAYA, I. S.、SOLOVEVA, N. P.、POLIEV+

  DOI：——

  日期：——
• A facile one-pot synthesis of novel substituted 1,2,3,4-tetrahydropyrimidine, part 2: Synthesis of 1-(aralkyl/aryl)-3-(alkyl/aralkyl/aryl)-5-aroyl-1,2,3,4-tetrahydropyrimidines
  作者：Kaushik Chanda、Milan Ch. Dutta、Enamul Karim、Jai N. Vishwakarma

  DOI：10.1002/jhet.5570410425

  日期：2004.7

  1-(Aralkyl/aryl)-3-(alkyyaralkyl)-5-aroyl-1,2,3,4-tetrahydropyrimidines (2a-c) have been synthesized by dethiomethylation of 5-aroyl-6-methylthio-1,2,3,4-tetrahydropyrimidines (1a-c). An alternative one-pot synthetic strategy has been developed for the title compounds 2a-t by the reaction of enaminones 3 with pri mary amine and formaldehyde in refluxing methanol in good yields.

  1-（芳烷基/芳基）-3-（烷基芳烷基）-5-芳酰基-1,2,3,4-四氢嘧啶（2a-c）是通过5-芳酰基-6-甲硫基1,2-的脱硫甲基化合成的， 3，4-四氢嘧啶（1a-c）。通过使烯胺酮3与主胺和甲醛在回流的甲醇中以良好的产率反应，已经开发了标题化合物2a-t的另一种单锅合成策略。
• Electrochemical multicomponent [2+2+1] cascade cyclization of enaminones and primary amines towards the synthesis of 4-acylimidazoles
  作者：Mingxu Wang、Ying Gao、Xiao-Jing Zhao、Lu Gao、Yonghui He

  DOI：10.1039/d3cc06196e

  日期：——

  An electrochemical multicomponent [2+2+1] cascade cyclization of enaminones and primary amines towards the synthesis of 4-acylimidazoles has been developed. In an undivided cell, enaminones and primary amines can smoothly participate in this reaction to provide a series of 1,2-disubstituted 4-acylimidazoles at room temperature. The reaction avoids the use of both transition-metal catalysts and oxidation

  烯胺酮和伯胺的电化学多组分[2+2+1]级联环化已被开发用于合成4-酰基咪唑。在未分裂的细胞中，烯胺酮和伯胺可以顺利地参与该反应，在室温下提供一系列1,2-二取代的4-酰基咪唑。该反应避免了使用过渡金属催化剂和氧化试剂，这使其更具可持续性和可再生性。