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。
• 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：——
• Experimental Support for Planar Pseudopericyclic Transition States in Thermal Cheletropic Decarbonylations
  作者：Han-Xun Wei、Chun Zhou、Sihyun Ham、Jonathan M. White、David M. Birney

  DOI：10.1021/ol048197d

  日期：2004.11.1

  Low-temperature crystal structures of three pyrrolediones (3-5) and a furandione (9) were obtained and compared to structurally related compounds that cannot undergo decarbonylation. Systematic trends in bond lengths and angles are consistent with distortions along the reaction coordinate, in accord with the structure correlation principle of Dunitz. Since the pyrroledione and furandione rings in 3-5 and 9 are planar, these ground-state geometries prefigure the calculated planar, pseudopericyclic transition states.