3-hydroxy-1-methyl-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-4-carboxylic acid ethyl ester | 20178-22-7

• 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: 3-hydroxy-1-methyl-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 4-hydroxy-1-methyl-5-oxo-2-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate；Ethyl 1-methyl-2-oxo-3-hydroxy-5-phenyl-3-pyrrolin-4-carboxylate；ethyl 4-hydroxy-1-methyl-5-oxo-2-phenyl-2H-pyrrole-3-carboxylate
• CAS: 20178-22-7
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: PEPBWEZHROLHSM-UHFFFAOYSA-N

物化性质

• 熔点：
  133 °C
• 沸点：
  465.9±45.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-1-methyl-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-4-carboxylic acid ethyl ester 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以79%的产率得到ethyl 4-hydroxy-1-methyl-5-oxo-2-phenylpyrrolidine-3-carboxylate
  参考文献：
  名称：

  Diastereoselective Reduction of 2,3-Dioxo-4-carboxy-5-substituted Pyrrolidines Using NaBH₄/AcOH and Heterogenous Hydrogenation Reactions

  摘要：

  $NaBH_4/AcOH$对2,3-二氧代-4-羧基-5-(取代)吡咯烷1的非对映选择性还原和异相氢化反应已得到报道。使用$^1H$ NMR和单晶X射线分析确定了产物的立体化学分配和非对映异构体比率。吡咯烷酮C-5取代基的空间位阻因素对还原产物的产率和非对映选择性都有显著影响。

  DOI：

  10.5012/jkcs.2015.59.1.31
• 作为产物：
  描述：

  4-ethoxycarbonyl-5-phenyl-N-methyldioxopyrroline 在 sodium disulfite 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.5h， 生成 3-hydroxy-1-methyl-2-oxo-5-phenyl-2,5-dihydro-1H-pyrrole-4-carboxylic acid ethyl ester
  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

• Synthesis and bioactivity of some 2-oxo-5-aryl-3-hydrazone and 2-oxo-5-aryl-4-hydrazone pyrrolidine derivatives
  作者：Mohd Fazli Mohammat、Nigar Najim、Nurul Shulehaf Mansor、Sharil Sarman、Zurina Shaameri、Mazatulikhma Mat Zain、Ahmad Sazali Hamzah

  DOI：10.3998/ark.5550190.0012.932

  日期：——

  ylate and 5-aryl-2,4-dioxopyrrolidine-3-carboxylate derivatives were successfully synthesized via carbonyl-based multiple component reaction and Dieckmann cyclization, respectively. Successive functional group transformations which include decarboxylation and hydrazonation afforded 2-oxo-5-aryl-3-hydrazone and 2-oxo-5-aryl-4hydrazone derivatives. Compound 3d exhibited activity against human histiocytic

  2-Aryl-4,5-dioxopyrrolidine-3-carboxylate 和 5-aryl-2,4-dioxopyrrolidine-3-carboxylate 衍生物分别通过基于羰基的多组分反应和 Dieckmann 环化反应成功合成。包括脱羧和腙的连续官能团转化得到2-氧-5-芳基-3-腙和2-氧-5-芳基-4腙衍生物。化合物 3d 对人组织细胞淋巴瘤 (U937) 和神经母细胞瘤 (SH-SY5Y) 细胞系表现出活性，而化合物 6 显示出对 H2O2 诱导的氧化应激介质的神经保护能力。
• Synthesis of 2,3-Dioxo-5-(substituted)arylpyrroles and Their 2-Oxo-5-aryl-3-hydrazone Pyrrolidine Derivatives
  作者：M. Mohammat、Z. Shaameri、A. Hamzah

  DOI：10.3390/molecules14010250

  日期：——

  Some novel 2,3-dioxo-5-(substituted)-arylpyrroles have been synthesized. Among these, pyrrolidine compound 1b was converted to 2,3-dioxo-5-aryl pyrrolidine 2b. Finally a set of hydrazone derivatives was obtained from the reaction of 2b with various hydrazine salts. The structures of all the new synthesized compounds were confirmed by elemental analyses, IR and 1H-NMR spectra.

  一些新的 2,3-dioxo-5-(取代)-arylpyrroles 已被合成。其中，吡咯烷化合物1b转化为2,3-二氧代-5-芳基吡咯烷2b。最后由2b与各种肼盐的反应获得了一组腙衍生物。所有新合成化合物的结构均通过元素分析、IR 和 1H-NMR 光谱证实。
• Synthesis of 5-aryl-2-oxopyrrole derivatives as synthons for highly substituted pyrroles
  作者：Bert Metten、Maarten Kostermans、Gitte Van Baelen、Mario Smet、Wim Dehaen

  DOI：10.1016/j.tet.2006.04.005

  日期：2006.6

  A small library of 2-oxo-5-(hetero)arylpyrroles was prepared starting from 2,3-dioxo-5-(hetero)arylpyrrolidines. The large synthetic possibilities of these 2-oxopyrroles were investigated. The 2-oxopyrroles offer a large number of possible derivatizations including reactions with electrophiles. The chloroformylation of 2-oxo-5-(hetero)arylpyrroles provides pyrrole carbaldehydes. Some pyrrole carbaldehydes were used to synthesize polycyclic compounds like pyrrolo[3,4-d]pyridazinones, a thienopyrrole, apyrrolobenz[1,4]oxazepine, a pyrrolobenzo[1,4]thiazepine, and a pyrrolobenzo[1,4]diazepine. Hereby we showed through a short exploration that the oxopyrroles and analogues are interesting and versatile synthetic building blocks. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of 2,3-Dialkoxy-1H-pyrrole via Reduction of Dioxopyrroline with Sodium Hydrosulfite
  作者：Takehiro Sano、Masaharu Seki、Jun Toda、Yoshisuke Tsuda

  DOI：10.3987/com-93-6479

  日期：——

  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.
• Diastereoselective Reduction of 2,3-Dioxo-4-carboxy-5-substituted Pyrrolidines Using NaBH₄/AcOH and Heterogenous Hydrogenation Reactions
  作者：Mohd Fazli Mohammat、Nurul Shulehaf Mansor、Zurina Shaameri、Ahmad Sazali Hamzah

  DOI：10.5012/jkcs.2015.59.1.31

  日期：2015.2.20

  Diastereoselective reduction of 2,3-dioxo-4-carboxy-5-(substituted)pyrrolidine 1 by $NaBH_4/AcOH$ and heterogenous hydrogenation were reported. Stereochemical assignment and diastereomeric ratios of the products were determined using $^1H$ NMR and single crystal X-ray analyses. The steric factors of the C-5 substituents of the pyrrolidinone was shown to have an interesting influence on both the yield and diastereoselectivity of the reduced product.

  $NaBH_4/AcOH$对2,3-二氧代-4-羧基-5-(取代)吡咯烷1的非对映选择性还原和异相氢化反应已得到报道。使用$^1H$ NMR和单晶X射线分析确定了产物的立体化学分配和非对映异构体比率。吡咯烷酮C-5取代基的空间位阻因素对还原产物的产率和非对映选择性都有显著影响。