4-ethoxycarbonyl-5-phenyl-N-benzyldioxopyrroline | 90788-38-8

• 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-ethoxycarbonyl-5-phenyl-N-benzyldioxopyrroline
• 英文别名: ethyl 1-benzyl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate；ethyl 1-benzyl-2-phenyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-3-carboxylate；ethyl 4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate；1-benzyl-5-phenyl-4-ethoxycarbonyl-1H-pyrrole-2,3-dione；ethyl 1-benzyl-4,5-dioxo-2-phenylpyrrole-3-carboxylate
• CAS: 90788-38-8
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: JDQQDSCLYLPTIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-ethoxycarbonyl-5-phenyl-N-benzyldioxopyrroline 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以73%的产率得到Ethyl 4-benzyl-5,6-dioxo-3-phenyl-1,4-oxazine-2-carboxylate
  参考文献：
  名称：

  Oxidation of Dioxopyproline with m-Chloroperbenzoic Acid: Selective Formation of 2,3-Dioxo-1,4-oxazine

  摘要：

  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.

  DOI：

  10.3987/com-93-s46
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 溶剂黄146 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 为溶剂， 反应 3.0h， 生成 4-ethoxycarbonyl-5-phenyl-N-benzyldioxopyrroline
  参考文献：
  名称：

  Sano, Takehiro; Horiguchi, Yoshie; Toda, Jun, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 2, p. 497 - 503

  摘要：

  DOI：

文献信息

• Three-Component Spiro Heterocyclization of Pyrrolediones, Indane-1,3-dione, and Heterocyclic Enamines
  作者：T. V. Salnikova、M. V. Dmitriev、A. N. Maslivets

  DOI：10.1134/s1070428019050117

  日期：2019.5

  ,2′,5,10-tetrahydro-1H-spiro(indeno[1,2-b]pyrazole[4,3-e]pyridine-4,3′-pyrroles) are formed via three-component spiro heterocyclization of 4-(ethoxycarbonyl)-5-phenyl-1Hpyrrole-2,3-diones and indane-1,3-dione with 5-amino-3-methylisoxazole or 5-amino-1H-pyrazoles.

  3-甲基-2'，5-二氧杂-5'-苯基-1'，2'，5,10-四氢螺（茚并[1,2- b ]异恶唑[4,3 - e ]吡啶-4,3' -吡咯）和2'，5-二氧杂-5'-苯基-1'，2'，5,10-四氢-1 H-螺（茚并[1,2- b ]吡唑[4,3- e ]吡啶-（4,3'-吡咯）是通过4-（乙氧羰基）-5-苯基-1 H吡咯-2,3-二酮和茚满-1,3-二酮与5-氨基-3的三组分螺旋杂环形成的-甲基异恶唑或5-氨基-1 H-吡唑。
• Substrate-dependent regiodivergent three-component condensation of 1H-pyrrole-2,3-diones, malononitrile and 4-hydroxyquinolin-2(1H)-ones
  作者：Tatyana V. Salnikova、Andrey A. Sabitov、Maksim V. Dmitriev、Andrey N. Maslivets、Michael Rubin

  DOI：10.1016/j.tet.2021.132129

  日期：2021.5

  three-component condensation of 1H-pyrrole-2,3-diones, malononitrile, and 4-hydroxyquinolin-2(1H)-ones was developed. The reaction can lead to the formation of spiro[pyrano[3,2-c]quinoline-4,3′-pyrrole] derivatives or the substituted 1,5-dihydropyrrole-2-ones depending on the substituents of 1H-pyrrole-2,3-diones and reaction conditions.

  开发了一种有效的区域发散性三组分缩合的1 H-吡咯-2,3-二酮，丙二腈和4-羟基喹啉-2（1 H）-ones。根据1 H-吡咯-的取代基，该反应可导致螺[吡喃并[3,2 - c ]喹啉-4,3'-吡咯]衍生物或取代的1,5-二氢吡咯-2-酮的形成。2,3-二酮和反应条件。
• Organocatalytic asymmetric Henry reaction of 1<i>H</i>-pyrrole-2,3-diones with bifunctional amine-thiourea catalysts bearing multiple hydrogen-bond donors
  作者：Ming-Liang Zhang、Deng-Feng Yue、Zhen-Hua Wang、Yuan Luo、Xiao-Ying Xu、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.3762/bjoc.12.31

  日期：——

  For the first time, a catalytic asymmetric Henry reaction of 1H-pyrrole-2,3-diones was achieved with a chiral bifunctional amine-thiourea as a catalyst possessing multiple hydrogen-bond donors. With this developed method, a range of 3-hydroxy-3-nitromethyl-1H-pyrrol-2(3H)-ones bearing quaternary stereocenters were obtained in acceptable yield (up to 75%) and enantioselectivity (up to 73% ee).

  首次使用手性双官能胺-硫脲作为具有多个氢键供体的催化剂，实现了1H-吡咯-2,3-二酮的催化不对称亨利反应。用这种发达的方法，以可接受的收率（高达75％）和对映选择性（高达73％ee）获得了一系列带有四级立体中心的3-羟基-3-硝基甲基-1H-吡咯-2（3H）-。
• One-pot, three-component synthesis of spiro[indeno[1,2-b]quinoline-10,3′-pyrroles] via the Hantzsch-type reaction of 1H-pyrrole-2,3-diones
  作者：Maksim V. Dmitriev、Tatyana V. Salnikova、Pavel S. Silaichev、Andrey N. Maslivets

  DOI：10.1016/j.tetlet.2016.11.100

  日期：2017.1

  A new methodology for the synthesis of spiro[indeno[1,2-b]quinoline-10,3′-pyrrole] derivatives via a Hantzsch-type reaction has been developed. This process involves the one-pot, three-component reaction of a 1H-pyrrole-2,3-dione, an aminocyclohexenone and 1,3-indanedione in acetic acid at reflux. Operationally simple, metal-free reaction conditions, simplicity of product isolation and good yields

  通过Hantzsch型反应合成螺[茚并[1,2 - b ]喹啉-10,3'-吡咯]衍生物的新方法已经开发出来。该过程涉及1 H-吡咯-2，3-二酮，氨基环己烯酮和1，3-茚满二酮在乙酸中的一锅三组分反应。操作简单，无金属的反应条件，产物分离的简单性和良好的收率是该方法的关键优势。
• Five-membered 2,3-dioxo heterocycles: LXX. Spiro heterocyclization of 1H-pyrrole-2,3-diones by the action of 1,5-binucleophiles. Crystalline and molecular structure of ethyl 1′-benzyl-7-methoxy-3,3-dimethyl-1,2′-dioxo-5′-phenyl-1′,2,2′,3,4,10-hexahydro-1H-spiro[acridine-9,3′-pyrrole]-4′-carboxylate
  作者：P. S. Silaichev、M. V. Dmitriev、Z. G. Aliev、A. N. Maslivets

  DOI：10.1134/s1070428010080105

  日期：2010.8

  Ethyl 1-alkyl-4,5-dioxo-2-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates reacted with 3-arylamino-5,5-dimethylcyclohex-2-en-1-ones as carbon-centered 1,5-binucleophiles to give the corresponding substituted ethyl 1′-alkyl-3,3-dimethyl-1,2′-dioxo-5′-phenyl-1′,2,2′,3,4,10-hexahydro-1H-spiro[acridine-9,3′-pyrrole]-4′-carboxylates whose structure was proved by X-ray analysis.

  1-烷基-4,5-二氧-2-苯基-4,5-二氢-1 H-吡咯-3-羧酸酯与3-芳基氨基5,5-二甲基环己-2-烯-1-酮反应生成碳中心的1,5-双亲核试剂得到相应的取代乙基1'-烷基-3,3-二甲基-1,2'-二氧代5'-苯基-1'，2,2'，3,4,10-六氢-1 H-螺[[啶-9,3'-吡咯] -4'-羧酸盐，其结构通过X射线分析证实。