2-benzoyl-4-oxo-4-(p-tolyl)butanenitrile

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2-benzoyl-4-oxo-4-(p-tolyl)butanenitrile
• 英文别名: 2-Benzoyl-4-(4-methylphenyl)-4-oxobutanenitrile
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: GZYQPNBCSBOJQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯丙炔醛 、 2-benzoyl-4-oxo-4-(p-tolyl)butanenitrile 在 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 sodium benzoate 作用下， 以 苯 为溶剂， 反应 12.0h， 以57%的产率得到
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

  摘要：

  In this paper, the first stereoselective annulation reaction between alpha-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.

  DOI：

  10.1021/ol3022287
• 作为产物：
  描述：

  苯甲酰乙腈 、 2-溴-4'-甲基苯乙酮 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以61%的产率得到2-benzoyl-4-oxo-4-(p-tolyl)butanenitrile
  参考文献：
  名称：

  N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals

  摘要：

  In this paper, the first stereoselective annulation reaction between alpha-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.

  DOI：

  10.1021/ol3022287

文献信息

• Synthesis of 1,4-Diketones by Michael Addition of O-Aroylmandelonitriles Involving Rearrangement of Aroyl Group and Decyanation.
  作者：Akira MIYASHITA、Yoshiyuki MATSUOKA、Atsushi NUMATA、Takeo HIGASHINO

  DOI：10.1248/cpb.44.448

  日期：——

  The anions derived form O-aroylmendelonitriles 1 reacted with Michael addition acceptors such as acrylonitrile (7) and methyl acrylate (10) to give the corresponding 1, 4-diketones 12, 13, and 15 in moderate to good yields. Under acidic conditions, the 1, 4-diketones 12, 13, and 15 were converted into the furans 17, 18 and 19 in good yields.

  O-aroylmendelonitriles 1 衍生出的阴离子与迈克尔加成受体（如丙烯腈 (7) 和丙烯酸甲酯 (10)）反应，得到相应的 1，4-二酮 12、13 和 15，收率中等至良好。在酸性条件下，1, 4-二酮 12、13 和 15 可以很好地转化为呋喃 17、18 和 19。
• N-Heterocyclic Carbene-Catalyzed Annulation of α-Cyano-1,4-diketones with Ynals
  作者：Fedor Romanov-Michailidis、Céline Besnard、Alexandre Alexakis

  DOI：10.1021/ol3022287

  日期：2012.9.21

  In this paper, the first stereoselective annulation reaction between alpha-cyano-1,4-diketones and ynals, mediated by catalytic amounts of a triazolium salt precatalyst and cocatalytic amounts of a weak carboxylate base, is disclosed. The title transformation proceeds smoothly under mild reaction conditions and generates three contiguous stereogenic centers, one of which is a quaternary acetal carbon. This reaction tolerates a wide variety of electronically distinct substituents on both reaction partners and affords privileged bicyclic scaffolds in 61-90% isolated yields and with up to 20:1 diastereomeric preference.