N-Phenyl-trans-styryl-trans-acrylamid | 34271-93-7

• 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: N-Phenyl-trans-styryl-trans-acrylamid
• 英文别名: (2E,4E)-N,5-diphenylpenta-2,4-dienamide
• CAS: 34271-93-7
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: QKPXQVORHNBNOI-HPIZBCMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (E)-N,5-diphenylpent-4-enamide 在 1,2-二苯亚磺酰基乙烷 、 palladium diacetate 、 copper(II) acetate monohydrate 、 三甲基乙酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到N-Phenyl-trans-styryl-trans-acrylamid
  参考文献：
  名称：

  钯催化不饱和酸和酰胺有氧脱氢合成共轭二烯

  摘要：

  已经证明了 Pd( II ) 催化的 γ,δ-烯酸和酰胺的直接需氧脱氢。本协议脱氢最少的酸性酰胺和酸，从而取代了传统的烯醇脱氢策略。以良好至优异的产率生产了广谱的共轭二酰胺和二烯酸。氘标记研究提出并支持了一种可能的反应机制。

  DOI：

  10.1039/d2cc02896d

文献信息

• Condensation of lithium diphenylphosphonium diylides with carbonic anhydride derivatives. A new one-pot synthesis of α,β-unsaturated anilides and amidines.
  作者：Henri-Jean Cristau、Anne Perraud-Darcy、Yves Ribeill

  DOI：10.1016/s0040-4039(00)79059-9

  日期：1992.5

  and dicyclohexylcarbodiimide. The formed semi-stabilised ylides bear a metallated amide or amidine function. Their use in situ as Wittig reagents towards aldehydes and ketones is shown to be a new one-pot, E-stereoselective synthesis for αβ-unsaturated anilides and amidines. Moreover, the corresponding phosphonium salts were isolated.

  二苯基锂phosph二锂容易腐蚀异氰酸苯酯和二环己基碳二亚胺。形成的半稳定化的亚基具有金属化的酰胺或am官能团。它们被原位用作维蒂希对醛和酮的试剂，被证明是一种新的一锅式E-立体选择性合成法，用于合成αβ-不饱和的酸酐和am。此外，分离了相应的phospho盐。
• Topochemistry. Part XXXI. Formation of cyclo-octa-1,5-cis,cis-dienes from 1,4-disubstituted s-trans-butadienes in the solid state. A contribution to the problem of C4-versus C8-cyclodimerisation
  作者：B. S. Green、M. Lahav、G. M. J. Schmidt

  DOI：10.1039/j29710001552

  日期：——

  Solid penta-1,3-diene-1-carboxylic acid (4), penta-1,3-diene-1-carboxamide (5), buta-1,3-diene-1,4-dicarbonitrile (6), styrylacrylic acid (10), its methyl ester (46), and amide (49)(all trans,trans-configurated), all photodimerise on irradiation (λ > 290 nm), to divinylcyclobutane (C4) derivatives. The structures of the fully characterised photoproducts from (4), (5), (6), and (49) and the light-stability

  固体1,5-3-二烯-1-羧酸（4），-1,3-二烯-1-羧酰胺（5），-1,3-二烯-1,4-二腈丁酯（6），苯乙烯基丙烯酸酸（10），其甲酯（46）和酰胺（49）（全部为反式，反式构型），均在照射（λ> 290 nm）后全部光二聚为二乙烯基环丁烷（C 4）衍生物。（4），（5），（6）和（49）的完全表征的光产物的结构和（N-苯基）苯乙烯基丙烯酰胺（53）的光稳定性可从已知或假定的包装方式中预测他们的单体。
• Monoamine oxidase inhibition by selected anilide derivatives
  作者：Lesetja Legoabe、Johann Kruger、Anél Petzer、Jacobus J. Bergh、Jacobus P. Petzer

  DOI：10.1016/j.ejmech.2011.08.036

  日期：2011.10

  A series of anilide derivatives were synthesized and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. The most potent inhibitors among the derivatives that were initially evaluated were (2E)-N-(3-chlorophenyl)-3-phenylprop-2-enamide (2c) and (2E)-N-(3-bromophenyl)-3-phenylprop-2-enamide (2d) with IC50 values of 0.53 mu M and 0.45 mu M, respectively. These derivatives exhibited reversible and selective inhibition of MAO-B with binding affinities 37 fold higher for MAO-B than for MAO-A. Analysis of the possible binding interactions of these inhibitors with active site models of human MAO-A and B led to the design of phenolic and benzonitrile derivatives of 2c and 2d. Among these were (2E)-N-(3-chlorophenyl)-3-(4-hydroxyphenyl)prop-2-enamide (7c) and (2E)-N-(3-bromophenyl)-3-(4-hydroxyphenyl)prop-2-enamide (7d) which inhibited MAO-B selectively and reversibly with IC50 values of 0.032 mu M and 0.026 mu M, respectively. These inhibitors were at least 14 fold more potent than 2c and 2d. This study concludes that N,3-diphenylprop-2-enamide is a suitable scaffold for the design of selective MAO-B inhibitors and structural modifications to enhance the binding affinities of the inhibitors for the MAO-B active site include substitution with halogens on the N-phenyl ring and substitution with hydroxyl and nitrile functional groups on the para and meta positions, respectively, of the C3 phenyl ring. Possible binding modes of these structures within the MAO-B active site are proposed with the emphasis on the interactions of the inhibitor halogens and the hydroxyl and nitrile functional groups with active site residues and water molecules. (C) 2011 Elsevier Masson SAS. All rights reserved.
• STEPANOVA O. S.; MAZURENKO G. A.; NGUEN BAH TXO; DERKACH N. YA., FIZIOL. AKTIVN. VESHCHESTVA. RESP. MEZHVED. SB. 1976, VYP. 8, 86-88
  作者：STEPANOVA O. S.、 MAZURENKO G. A.、 NGUEN BAH TXO、 DERKACH N. YA.

  DOI：——

  日期：——