2-amino-3-benzoyl-1,4-diphenylbut-2-ene-1,4-dione | 95548-89-3

• 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-amino-3-benzoyl-1,4-diphenylbut-2-ene-1,4-dione
• 英文别名: 1-amino-1,2,2-tribenzoylethene；Haopd
• CAS: 95548-89-3
• 化学式: C₂₃H₁₇NO₃
• 分子量: 355.393
• InChiKey: ONMJZOBCXDMZSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.23
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  palladium diacetate 、 2-amino-3-benzoyl-1,4-diphenylbut-2-ene-1,4-dione 以 乙醇 为溶剂， 以62%的产率得到Pd(aopd-N,O)2
  参考文献：
  名称：

  N,O versus O,O coordination in β-imino diketonato complexes: Role of the metal center and of the imino substituent

  摘要：

  beta-Imino carbonyl enolato metal(II) complexes of general formula [M((RCO)(R'CO)CC(R '') NH)(2)] (M = Mn, Fe, Co, Ni, Cu, Zn, Pd, R = R' = Me, R '' = CCl(3); M = Cu, Pd, R = R' = Me, R '' = PhCO; R = Me, R' = Ph, R '' = PhCO; R = R' = Ph, R '' = PhCO) are easily synthesized by the reaction of metal(II) acetates with the proper beta-enaminodiones in 1/2 molar ratio in ethanol at room temperature. In all the cases the trifunctional NOO beta-imino carbonyl enolate ligand acts as bidentate to give ML(2) complexes, whose structure depends on the metal center and on the nature of the substituent R '' at the imino carbon. With R '' = CCl(3) an O,O coordination is observed for all the metal centers but one, in fact palladium(II) exhibits an N,O coordination through the imino nitrogen and one keto oxygen. By contrast with R '' = PhCO the ligand is always coordinated through the imino nitrogen and one keto oxygen atom. (C) 2008 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2008.05.003
• 作为产物：
  描述：

  苯甲酰腈 、 二苯甲酰基甲烷 在 Ni (pentane-2,4-dione-yl)2 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 以73%的产率得到2-amino-3-benzoyl-1,4-diphenylbut-2-ene-1,4-dione
  参考文献：
  名称：

  金属催化的β-二碳化合物加成到苯甲酰氰的腈碳中。1-氨基-1-苯甲酰基-2,2-二酰基乙烯的合成

  摘要：

  配合物[Ni（acac）2 ]（Hacac pentane -2,4-dione）选择性催化将β-二酮的羰基间碳原子加成至苯甲酰氰的氰基中，而通常的碱性有机催化剂会导致对羰基的攻击C N基团取代的碳原子。

  DOI：

  10.1039/c39840001593

文献信息

• Metal-catalysed addition of β-dicarbony compounds to the nitrile carbon of benzoyl cyanide. Synthesis of 1-amino-1-benzoyl-2,2-diacylethenes
  作者：Marino Basato、Benedetto Corain、Marino Cofler、Augusto C. Veronese、Giuseppe Zanotti

  DOI：10.1039/c39840001593

  日期：——

  The complex [Ni(acac)2](Hacac pentane-2,4-dione) selectively catalyses addition of the intercarbonylic carbon atom of β-diketones to the cyano group of benzoyl cyanide, whereas usual basic organic catalysts lead to attack on the carbonyl carbon atom with displacement of the CN group.

  配合物[Ni（acac）2 ]（Hacac pentane -2,4-dione）选择性催化将β-二酮的羰基间碳原子加成至苯甲酰氰的氰基中，而通常的碱性有机催化剂会导致对羰基的攻击C N基团取代的碳原子。
• Carbon-carbon bond formation in the reaction of benzoyl cyanide with nickel(<scp>II</scp>)β-diketonates
  作者：Marino Basato、Umberto Casellato、Rodolfo Graziani、Augusto C. Veronese

  DOI：10.1039/dt9920001193

  日期：——

  Nickel beta-diketonates react with benzoyl cyanide to give C-C bond formation between the methine and the cyano carbon atoms. The resulting reddish compounds are square-planar iminodiketonato complexes, which are likely catalytic intermediates in the synthesis of beta-enaminodiones from beta-diketones and PhCOCN. The acetylacetonato derivative [Ni(acac.PhCOCN)2] can be obtained in the solid state in two stable forms; an X-ray single-crystal analysis of form II indicates that the unit cell [monoclinic, space group P2(1)/c, a = 11.408(5) angstrom, b = 15.109(4) angstrom, c = 14.515(5) angstrom, beta = 108.93(3)-degrees] contains two couples of independent, structurally very similar, molecules of the complex. The nickel atom is always centrosymmetrically co-ordinated to the ligand in a N,O bonding configuration, which is preferred to the alternative O,O one.
• BASATO, M.;CORAIN, B.;COFLER, M.;VERONESE, A. C.;ZANOTTI, G., J. CHEM. SOC. CHEM. COMMUN., 1984, N 23, 1593-1594
  作者：BASATO, M.、CORAIN, B.、COFLER, M.、VERONESE, A. C.、ZANOTTI, G.

  DOI：——

  日期：——
• Veronese, Augusto C.; Callegari, Rosella; Basato, Marino, Journal of the Chemical Society. Perkin transactions I, 1994, # 13, p. 1779 - 1786
  作者：Veronese, Augusto C.、Callegari, Rosella、Basato, Marino、Valle, Giovanni

  DOI：——

  日期：——
• N,O versus O,O coordination in β-imino diketonato complexes: Role of the metal center and of the imino substituent
  作者：Marino Basato、Marzio Bortolussi、Elena Faggin、Cristina Tubaro、Augusto Cesare Veronese

  DOI：10.1016/j.ica.2008.05.003

  日期：2009.1

  beta-Imino carbonyl enolato metal(II) complexes of general formula [M((RCO)(R'CO)CC(R '') NH)(2)] (M = Mn, Fe, Co, Ni, Cu, Zn, Pd, R = R' = Me, R '' = CCl(3); M = Cu, Pd, R = R' = Me, R '' = PhCO; R = Me, R' = Ph, R '' = PhCO; R = R' = Ph, R '' = PhCO) are easily synthesized by the reaction of metal(II) acetates with the proper beta-enaminodiones in 1/2 molar ratio in ethanol at room temperature. In all the cases the trifunctional NOO beta-imino carbonyl enolate ligand acts as bidentate to give ML(2) complexes, whose structure depends on the metal center and on the nature of the substituent R '' at the imino carbon. With R '' = CCl(3) an O,O coordination is observed for all the metal centers but one, in fact palladium(II) exhibits an N,O coordination through the imino nitrogen and one keto oxygen. By contrast with R '' = PhCO the ligand is always coordinated through the imino nitrogen and one keto oxygen atom. (C) 2008 Elsevier B. V. All rights reserved.