4-benzoyl-1,5-diphenyl-2,3-dihydropyrrole-2,3-dione | 36684-30-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-benzoyl-1,5-diphenyl-2,3-dihydropyrrole-2,3-dione
• 英文别名: 4-benzoyl-1,5-diphenyl-1H-pyrrole-2,3-dione；4-Benzoyl-1,5-diphenyl-1H-pyrrol-2,3-dion；4-benzoyl-1,5-diphenyl-pyrrole-2,3-dione；4-Benzoyl-1,5-diphenyl-4-pyrrolin-2,3-dion；1H-Pyrrole-2,3-dione, 4-benzoyl-1,5-diphenyl-；4-benzoyl-1,5-diphenylpyrrole-2,3-dione
• CAS: 36684-30-7
• 化学式: C₂₃H₁₅NO₃
• 分子量: 353.377
• InChiKey: VSSMHMHHPCJUHI-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  522.7±60.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-benzoyl-1,5-diphenyl-2,3-dihydropyrrole-2,3-dione 在 sodium disulfite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 生成 4-[hydroxy(phenyl)methylidene]-1,5-diphenylpyrrolidine-2,3-dione
  参考文献：
  名称：

  Synthesis of 2,3-Dialkoxy-1H-pyrrole via Reduction of Dioxopyrroline with Sodium Hydrosulfite

  摘要：

  Reduction of IH-pyrrole-2,3-dione (3 and 7) with sodium hydrosulfite took place selectively in a 1,4-manner. Methylation of the product with diazomethane gave 1,5-dihydro-3-methoxy-2H-pyrrol-2-one (5 and 8) in good yield. Treatment of the methyl ether (5 or 8) with triethyloxonium tetrafluoroborate caused ethylation of the lactam carbonyl with concomitant deprotonation to give 2,3-dialkoxy-1H-pyrrole (9). This conversion provides a simple synthetic method of 2,3-dialkoxypyrroles.

  DOI：

  10.3987/com-93-6479
• 作为产物：
  描述：

  5-Phenyl-4-<α-(phenylimino)benzyl>-2,3-furandion 以41%的产率得到4-benzoyl-1,5-diphenyl-2,3-dihydropyrrole-2,3-dione
  参考文献：
  名称：

  Kollenz, Gert; Penn, Gerhard; Dolenz, Gerhard, Chemische Berichte, 1984, vol. 117, # 4, p. 1299 - 1309

  摘要：

  DOI：

文献信息

• Dioxopyrrolines. Part LVIII. Rearrangement of 2,3-Dioxo-1,4-oxazines to 4,5-Dioxooxazoles in the Reaction with Dimethylsulfoxonium Methylide.
  作者：Jun TODA、Masaharu SEKI、Kazuko AMANO、Taichi OYAMA、Takehiro SANO、Fumiyuki KIUCHI、Yoshisuke TSUDA

  DOI：10.1248/cpb.42.739

  日期：——

  Reaction of 2, 3-dioxo-2, 3-dihydro-4H-1, 4-oxazines 2a-e with dimethylsulfoxonium methylide introduced an exo-methylene group with concomitant ring contraction to give 4, 5-dioxo-2, 3, 4, 5-tetrahydrooxazoles 3a-e in moderate yields. Mechanism of this unusual reaction was discussed.

  2, 3-二酮-2, 3-二氢-4H-1, 4-噁唑啉 2a-e 与二甲基亚磺酸钠甲基负离子的反应引入了一个外部亚甲基组，同时伴随环收缩，生成了4, 5-二酮-2, 3, 4, 5-四氢噁唑 3a-e，产率适中。讨论了这一非寻常反应的机制。
• Reactions of cyclic oxalyl compounds - 32.
  作者：Ewald Terpetschnig、Gerhard Penn、Gert Kollenz、Karl Peters、Eva-Maria Peters、Hans Georg von Schnering

  DOI：10.1016/s0040-4020(01)96034-x

  日期：1991.5

  The heterocyclic 2,3-diones 1 – 3 have been found to undergo photochemical and thermal 2+2-cycloaddition reactions via their 3-carbonyl group to diphenylketene and the diphenylketen-N-(4-methylphenyl)-imine. These reactions afford rearranged cycloadducts as well as 2+2-cycloreversion products.

  杂环-2,3-二酮1 - 3已发现经历光化学和热2 +经由他们的3-羰基-2-环加成反应二苯基乙烯酮以与diphenylketen-N-（4-甲基苯基） -亚胺。这些反应提供了重排的环加合物以及2 + 2-环还原产物。
• Ziegler,E. et al., Justus Liebigs Annalen der Chemie, 1976, p. 2071 - 2082
  作者：Ziegler,E. et al.

  DOI：——

  日期：——
• Kollenz, Gert; Penn, Gerhard; Ott, Walter, Chemische Berichte, 1984, vol. 117, # 4, p. 1310 - 1329
  作者：Kollenz, Gert、Penn, Gerhard、Ott, Walter、Peters, Karl、Peters, Eva-Maria、et al.

  DOI：——

  日期：——
• Oxidation of Dioxopyproline with m-Chloroperbenzoic Acid: Selective Formation of 2,3-Dioxo-1,4-oxazine
  作者：Takehiro Sano、Kazuko Amono、Masaharu Seki、Hiroyuki Hirota、Jun Toda、Fumiyuki Kiuchi、Yoshisuke Tsuda

  DOI：10.3987/com-93-s46

  日期：——

  Treatment of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-diones (1a-1e) and 4-benzoyl-1,5-diphenyl-1H-pyrrole-2,3-dione (1f) with m-chloroperbenzoic acid caused Baeyer-Villiger oxidation to give 2,3-dioxo-1,4-oxazines (2a-2f) in moderate yields, respectively. This conversion of the 1H-pyrrole-2,3-dione into the 2,3-dioxo-1,4-oxazine provides the first synthesis of monocyclic 2,3-dioxo-1,4-oxazine ring system.