4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione | 59046-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione
• 英文别名: 1-Phenyl-2-ethoxycarbonyl-3-benzoyl-Δ²-pyrrolin-4,5-dion；3-benzoyl-4,5-dioxo-1-phenyl-4,5-dihydro-pyrrole-2-carboxylic acid ethyl ester；4-Benzoyl-1-phenyl-5-ethoxycarbonyl-1h-pyrrole-2,3-dione；ethyl 3-benzoyl-4,5-dioxo-1-phenylpyrrole-2-carboxylate
• CAS: 59046-35-4
• 化学式: C₂₀H₁₅NO₅
• 分子量: 349.343
• InChiKey: RCIFLMCZLXZMTF-UHFFFAOYSA-N

物化性质

• 沸点：
  487.4±55.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-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
  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

文献信息

• Dioxopyrrolines. LX. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione to Olefins: An Inverse-Electron-Demand Hetero Diels-Alder Reaction.
  作者：Yoshie HORIGUCHI、Takehiro SANO、Yoshisuke TSUDA

  DOI：10.1248/cpb.44.670

  日期：——

  Thermal cycloaddition of 4-benzoyl-5-ethoxycarbonyl-1-phenyl-1H-Pyrrole-2, 3-dione (dioxopyrroline) 1 to electron-rich olefins smoothly proceeded in a highly regio- and stereoselective manner to give pyranopyrrole derivatives in excellent yields. The reaction is a typical inverse-electron-demand hetero Diels-Alder reaction, in which dioxopyrroline behaves as an electron-deficient diene.

  4-苯甲酰基-5-乙氧羰基-1-苯基-1H-吡咯-2,3-二酮（二氧吡咯啉）与富电子烯烃的热环加成反应顺利进行，以高度区域选择性和立体选择性的方式生成吡喃吡咯衍生物，产率极佳。该反应为典型的逆电子需求杂Diels-Alder反应，其中二氧吡咯啉作为缺电子二烯参与反应。
• Diversity-oriented synthesis of three skeletally diverse iminolactones from isocyanides, activated acetylenes and 1H-pyrrole-2,3-diones via [3+2] and [4+1] cycloaddition reactions
  作者：Anna A. Moroz、Vladimir E. Zhulanov、Maksim V. Dmitriev、Andrey N. Maslivets

  DOI：10.1016/j.tet.2019.130880

  日期：2020.1

  facile method for the synthesis of two distinct iminolactones spiroannulated by pyrrole in one reaction was developed through the three-component [3 + 2] cycloaddition of 1H-pyrrole-2,3-diones and in situ generated dipoles from isocyanides and acetylenes. The [4 + 1] cycloaddition reaction of 4-aroyl substituted 1H-pyrrole-2,3-diones and isocyanides was utilized for the synthesis of iminolactones fused

  通过1 H-吡咯-2,3-二酮的三组分[3 + 2]环加成反应，并从异氰酸酯和乙炔中原位生成偶极子，开发了一种简便的方法，可在一个反应​​中合成由吡咯环化的两个不同的亚氨基内酯。利用4-芳酰基取代的1 H-吡咯-2，3-二酮与异氰酸酯的[4 +1]环加成反应合成吡咯在[ c ]侧稠合的亚氨基内酯。这些协议的优点包括温和的无催化剂反应条件，以及可接触具有骨架多样性的三种类型的杂环。
• Formal [3+3] Cyclocondensation of 4-Acyl-1H-pyrrole-2,3-diones with Five-Membered Cyclic Enamines To Form Substituted 1H-Py­razolo[3,4-b]pyridines and Isoxazolo[5,4-b]pyridines
  作者：Аndrey Maslivets、Alexey Dubovtsev、Maksim Dmitriev、Pavel Silaichev、Dmitriy Antonov

  DOI：10.1055/s-0036-1588407

  日期：——

  substituted 1H-pyrazolo[3,4-b]pyridines and isoxazolo[5,4-b]pyridines was developed through the formal [3+3] cascade cyclocondensation of 4-acyl-1H-pyrrole-2,3-diones as 1,3-bis-electrophiles with the five-membered cyclic enamines as 1,3-bis-nucleophiles. A highly efficient method for the preparation of multifunctional substituted 1H-pyrazolo[3,4-b]pyridines and isoxazolo[5,4-b]pyridines was developed through

  摘要 通过4-酰基-1的正式[3 + 3]级联环缩合反应，开发了一种高效的制备多功能取代的1 H-吡唑并[3,4- b ]吡啶和异恶唑并[5,4- b ]吡啶的方法。H-吡咯-2,3-二酮为1,3-双亲电子试剂，五元环烯胺为1,3-双亲核试剂。 通过4-酰基-1的正式[3 + 3]级联环缩合反应，开发了一种高效的制备多功能取代的1 H-吡唑并[3,4- b ]吡啶和异恶唑并[5,4- b ]吡啶的方法。H-吡咯-2,3-二酮为1,3-双亲电子试剂，五元环烯胺为1,3-双亲核试剂。
• Dioxopyrrolines. LXI. Cycloaddition Reaction of 4-Benzoyl-5-ethoxycarbonyl-1-phenyl-1H-pyrrole-2,3-dione with 1,3-Dienes: Competitive Occurrence of Normal and Hetero Diels-Alder Reaction and Claisen Rearrangement of the Hetero Diels-Alder Product.
  作者：Yoshie HORIGUCHI、Takehiro SANO、Fumiyuki KIUCHI、Yoshisuke TSUDA

  DOI：10.1248/cpb.44.681

  日期：——

  Thermal cycloaddition reaction of 4-benzoyl-5-ethoxycarbonyl-1H-pyrrole-2, 3-dione (dioxopyrroline) 1 with 1, 3-dienes caused two types of Diels-Alder (D-A) reaction in a competitive manner. One is the hetero D-A reaction in whch dioxopyrroline acts as an electron-deficient diene and the 1, 3-diene acts as an electron-rich dienophile. The other is the normal D-A reaction in which diosopyrroline acts as an electron-deficient dienophile. The 1, 3-dienes bearing electron-rich substituents undergo the D-A reaction via the normal pathway, while the 1, 3-dienes which do not bear an electron-donating group predominantly undergo the hetero D-A reaction. When the normal D-A pathway is sterically hindered, the hetero D-A pathway occurs exclusively.

  4-苯甲酰基-5-乙氧基羰基-1H-吡咯-2, 3-二酮（二氧代吡咯啉）1与1, 3-二烯的热环加成反应以竞争方式引起两种类型的狄尔斯-阿尔德（D-A）反应。一种是杂D-A反应，其中二氧代吡咯啉充当缺电子二烯，1, 3-二烯充当富电子亲二烯体。另一种是正常的 D-A 反应，其中二代吡咯啉充当缺电子亲二烯体。带有富电子取代基的1, 3-二烯通过正常途径进行D-A反应，而不带有给电子基团的1, 3-二烯主要进行杂D-A反应。当正常的 D-A 途径受到空间阻碍时，异源 D-A 途径会排他地发生。
• Tsuda,Y. et al., Heterocycles, 1976, vol. 4, p. 1237 - 1242
  作者：Tsuda,Y. et al.

  DOI：——

  日期：——