4,5-diphenyl-2,3-dihydro-2,3-furandione | 146463-39-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,5-diphenyl-2,3-dihydro-2,3-furandione
• 英文别名: 4,5-diphenyl-2,3-dihydrofuran-2,3-dione；4,5-diphenylfuran-2,3-dione
• CAS: 146463-39-0
• 化学式: C₁₆H₁₀O₃
• 分子量: 250.254
• InChiKey: QXSVEMMTKASTIF-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  410.0±55.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-diphenyl-2,3-dihydro-2,3-furandione 在 diphenyl ether-biphenyl eutectic 作用下， 以 xylene 为溶剂， 生成 N-(4-methoxy-phenyl)-3-oxo-2,3-diphenyl-propionamide
  参考文献：
  名称：

  摘要：

  Aroyl(phenyl)ketenes generated by thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones undergo [4+2]-cyclodimerization to 3-aroyl-6-aryl-3,5-diphenyl-3,4-dihydro-2H-pyran-2,4-diones. Heating of the latter leads to rearrangement with formation of 4-aroyloxy-6-aryl-3,5-diphenyl-2H-pyran-2-ones. Thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones in the presence of carbonyl compounds yields 6-aryl-5-phenyl-4H-1,3-dioxin-4-ones.

  DOI：

  10.1023/a:1023454915387
• 作为产物：
  描述：

  草酰氯 、 desoxybenzoin trimethylsilyl ether 以 氯仿 为溶剂， 反应 2.0h， 以50%的产率得到4,5-diphenyl-2,3-dihydro-2,3-furandione
  参考文献：
  名称：

  Maslivets, A. N.; Tarasova, O. P.; Andreichikov, Yu. S., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.2, p. 1011 - 1018

  摘要：

  DOI：

文献信息

• Domino reactions of 2<i>H</i>-azirines with acylketenes from furan-2,3-diones: Competition between the formation of <i>ortho</i>-fused and bridged heterocyclic systems
  作者：Alexander F Khlebnikov、Mikhail S Novikov、Viktoriia V Pakalnis、Roman O Iakovenko、Dmitry S Yufit

  DOI：10.3762/bjoc.10.74

  日期：——

  prepared only from 3-aryl-2H-azirines having no electron-withdrawing groups in the aryl substituent. Calculations at the DFT B3LYP/6-31G(d) level for the various routes of bis[1,3]oxazino[3,2-a:3',2'-d]pyrazine skeleton formation revealed a new domino reaction of 3-aryl-2H-azirines occurring in the presence of furandiones: acid-catalyzed dimerization to dihydropyrazine followed by consecutive cycloaddition

  3-芳基-2H-氮丙啶与通过 5-芳基呋喃-2,3-二酮热解产生的酰基乙烯酮反应，得到桥联 5,7-二氧杂-1-氮杂双环[4.4.1]undeca-3,8-二烯- 2,10-二酮和/或邻位稠合的6,6a,12,12a-四氢双[1,3]恶嗪基[3,2-a:3',2'-d]吡嗪-4,10-二酮。后者具有新的杂环骨架，是两分子氮丙啶和两分子酰基乙烯酮偶联的结果，并且只能由芳基取代基中不具有吸电子基团的3-芳基-2H-氮丙啶制备。在 DFT B3LYP/6-31G(d) 水平上对双[1,3]恶嗪基[3,2-a:3',2'-d]吡嗪骨架形成的各种途径的计算揭示了新的多米诺骨牌反应 3 -芳基-2H-氮丙啶在呋喃二酮存在下发生：酸催化二聚成二氢吡嗪，然后将后者连续环加成到两个酰基乙烯酮分子上。
• Maslivets, A. N.; Tarasova, O. P.; Andreichikov, Yu. S., Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 6.2, p. 1011 - 1018
  作者：Maslivets, A. N.、Tarasova, O. P.、Andreichikov, Yu. S.

  DOI：——

  日期：——
• Five-Membered 2,3-Dioxo Heterocycles: XLVII. Reaction of 5-Aryl-4-phenyl-2,3-dihydrofuran-2,3-diones with Compounds Containing C = N and C N Bonds
  作者：E. S. Vostrov、E. V. Leont’eva、O. P. Tarasova、A. N. Maslivets

  DOI：10.1023/b:rujo.0000045204.07277.72

  日期：2004.7

  Thermal decarbonylation of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones gives rise to intermediate aroyl(phenyl)ketenes which react with nonactivated Schiff bases, N,N'-dicyclohexylcarbodiimide, and p-dimethylaminobenzonitrile according to the [4+2]-cycloaddition pattern with formation of 6-aryl-5-phenyl-4H-1,3-oxazin-4-ones. Reactions of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones with activated Schiff bases at a temperature below the thermolysis temperature lead to 4-aroyl-4-phenyltetrahydropyrrole-2,3-diones.
• ——
  作者：E. S. Vostrov、N. Yu. Lisovenko、O. P. Tarasova、A. N. Maslivets

  DOI：10.1023/a:1013256406113

  日期：——
• ——
  作者：E. S. Vostrov

  DOI：10.1023/a:1023454915387

  日期：——

  Aroyl(phenyl)ketenes generated by thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones undergo [4+2]-cyclodimerization to 3-aroyl-6-aryl-3,5-diphenyl-3,4-dihydro-2H-pyran-2,4-diones. Heating of the latter leads to rearrangement with formation of 4-aroyloxy-6-aryl-3,5-diphenyl-2H-pyran-2-ones. Thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones in the presence of carbonyl compounds yields 6-aryl-5-phenyl-4H-1,3-dioxin-4-ones.