ethyl 4-hydroxy-1-methyl-2-(4-methylphenyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate | 1174005-13-0

• 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: ethyl 4-hydroxy-1-methyl-2-(4-methylphenyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
• CAS: 1174005-13-0
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: MKOLYYOYNKGDGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-1-methyl-2-(4-methylphenyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate 在 甲酸 、 palladium hydroxide, 20 wt% on carbon 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 ethyl 4-(2-hydroxyethylamino)-1-methyl-2-(4-methylphenyl)-5-oxopyrrolidine-3-carboxylate
  参考文献：
  名称：

  Facile Reduction of β-Enamino Oxopyrrolidine Carboxylates Mediated by Heterogeneous Palladium Catalyst

  摘要：

  The synthesis of diastereoisomers via diastereoselective hydrogenation of unreactive endocyclic enamine system of ethyl 4-hydrazinyl- and 4-(2-hydroxyethylamino)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylates using palladium-based catalyst was developed. The steric and electronic properties of substituents, especially of the C(2)substituent, influenced both the yield and diastereoselectivity. Despite the reaction generated three chiral centers, the reduced compounds had eithercis-transor all-transconfiguration which was successfully determined by means of 1D and 2D NMR experiments.

  DOI：

  10.1134/s1070428020060184
• 作为产物：
  描述：

  对甲基苯甲醛 、 甲胺 、 sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate 以 乙醇 、 水 为溶剂， 生成 ethyl 4-hydroxy-1-methyl-2-(4-methylphenyl)-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  研究合成γ-内酰胺杂环化合物对耐甲氧西林金黄色葡萄球菌菌株的抗菌作用并评估先导化合物MFM514的安全性和有效性

  摘要：

  耐甲氧西林金黄色葡萄球菌 (MRSA) 仍然是世界所有地区医院获得性感染的主要原因之一，而利奈唑胺是针对这种危险的革兰氏阳性病原体的仅有的市售口服抗生素之一。在这项研究中，确定了 32 种合成 γ-内酰胺杂环类似物对 MRSA 的抗菌活性。在用于最低抑菌浓度 (MIC) 测定的筛选类似物中，化合物 MFM514 对 30 种 MRSA 和 12 种甲氧西林敏感金黄色葡萄球菌 (MSSA) 临床分离株显示出良好的抑制活性，MIC 值为 7.8–15.6 µg/mL，同时细胞毒性评估显示平均抑制浓度 (IC50) 值 > 625 µg/mL，显示出成为先导化合物的潜力。在随后的 MFM514 动物研究中，单剂量口服急性毒性试验显示估计平均致死剂量 (LD50) 值 <5000 mg/kg，而在小鼠感染试验中，通过口服获得的平均有效剂量 (ED50) 值为 29.39 mg/kg . 这些结果表明，γ-内酰胺碳骨架，特别是

  DOI：

  10.3390/molecules28062575

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。
• 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。
• Concise strategy for diastereoselective annulation to afford fused [5:7] oxazepanone γ-lactams
  作者：Fatin Nur Ain Abdul Rashid、Mohd Fazli Mohammat、Nurul Shulehaf Mansor、Zurina Shaameri、Ahmad Sazali Hamzah

  DOI：10.24820/ark.5550190.p011.618

  日期：——