Methyl 3-(4-bromobenzoyl)-1-(4-methylphenyl)-4,5-dioxopyrrole-2-carboxylate | 1198797-05-5

• 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: Methyl 3-(4-bromobenzoyl)-1-(4-methylphenyl)-4,5-dioxopyrrole-2-carboxylate
• CAS: 1198797-05-5
• 化学式: C₂₀H₁₄BrNO₅
• 分子量: 428.239
• InChiKey: PLRWJURNWDKEQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  5
• 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：

  苯基脲 、 Methyl 3-(4-bromobenzoyl)-1-(4-methylphenyl)-4,5-dioxopyrrole-2-carboxylate 以 甲苯 为溶剂， 反应 0.17h， 以92%的产率得到methyl 3-(4-bromobenzoyl)-4-hydroxy-5-oxo-2-[(phenylcarbamoyl)amino]-1-(p-tolyl)-2,5-dihydro-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  由5-烷氧羰基-1 H-吡咯-2,3-二酮和苯脲合成咪唑螺环化合物

  摘要：

  5-烷氧基羰基取代的1 H-吡咯-2,3-二酮与苯基脲反应，形成烷基4-羟基-5-氧代-2-[（苯基氨基甲酰基）氨基] -2,5-二氢-1 H-吡咯-2 -羧酸盐，其在甲醇钠存在下环化，得到8-羟基-3-苯基-1,3,6-三氮杂螺[4.4]-非-8-烯-2,4,7-三酮。8-羟基-9-（4-甲基苯甲酰基）-3-苯基-6-（对甲苯基）-1,3,6-三氮杂螺[4.4] non-8-ene-2,4,7-的晶体结构研究了三酮和8-羟基-2,4,7-三氧代-3,6-二苯基-1,3,6-三氮杂螺[4.4]非-8-烯-9-羧酸甲酯。

  DOI：

  10.1007/s10593-016-1913-8

文献信息

• Spiro-condensation of 5-methoxycarbonyl-1H-pyrrole-2,3-diones with cyclic enoles to form spiro substituted furo[3,2-c]-coumarins and quinolines
  作者：Alexey Yu. Dubovtsev、Pavel S. Silaichev、Mikhail A. Nazarov、Maksim V. Dmitriev、Andrey N. Maslivets、Michael Rubin

  DOI：10.1039/c6ra16889b

  日期：——

  Highly efficient spiro-cyclization enabling cyclic enoles to act as 1,3-bis-nucleophiles in reaction with pyrrole-2,3-diones acting as 1,2-bis-electrophiles was developed.

  高效的螺环闭合反应使得环状烯醇能够作为1,3-双亲核试剂与作为1,2-双电亲试剂的吡咯-2,3-二酮发生反应。
• 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。
• Regiodivergent condensation of 5-alkoxycarbonyl-1<i>H</i>-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds
  作者：Alexey Yu Dubovtsev、Maksim V Dmitriev、Аndrey N Maslivets、Michael Rubin

  DOI：10.3762/bjoc.13.218

  日期：——

  between two alternative directions affording derivatives of partially hydrogenated indole or benzofurane. The control of this regioselectivity is efficiently governed by steric effects at the hydrazone moiety of the ketazinone reagent.

  系统地研究了5-烷氧基羰基-1H-吡咯二酮与环状酮嗪酮的缩合。发现该反应的区域选择性可以容易地在两个替代方向之间交换，从而提供部分氢化的吲哚或苯并呋喃的衍生物。该区域选择性的控制有效地由酮嗪酮试剂的moiety部分处的空间效应控制。
• Five-membered 2,3-dioxo heterocycles: CV. Reaction of methyl 1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with methyl 2-arylamino-4-(2-naphthyl)-4-oxobut-2-enoates. Crystal and molecular structure of substituted 1,7-diazaspiro[4.4]nonane
  作者：E. S. Denislamova、A. Yu. Dubovtsev、P. A. Slepukhin、A. N. Maslivets

  DOI：10.1134/s1070428014070148

  日期：2014.7
• Five-membered dioxoheterocycles: XCIX. Reaction of 1-aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones with indoles. Crystal and molecular structure of substituted 2-(indol-3-yl)pyrrole
  作者：E. S. Denislamova、P. A. Slepukhin、A. N. Maslivets

  DOI：10.1134/s1070428014020146

  日期：2014.2

  1-Aryl-4-aroyl-5-methoxycarbonyl-1H-pyrrole-2,3-diones react with indole and 2-methylindole with the formation of methyl 1-aryl-3-aroyl-4-hydroxy-2-(1H-indol-3-yl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylates. Crystal and molecular structure of methyl 3-benzoyl-4-hydroxy-2-(2-methyl-1H-indol-3-yl)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-2-carboxylate was examined.