ethyl 4-hydroxy-2-(4-methoxyphenyl)-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate | 904604-04-2

• 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-2-(4-methoxyphenyl)-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
• CAS: 904604-04-2
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: HMOVZUWWQZVFJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-hydroxy-2-(4-methoxyphenyl)-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate 在 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)-2-(4-methoxyphenyl)-1-methyl-5-oxopyrrolidine-3-carboxylate
  参考文献：
  名称：

  Concise strategy for diastereoselective annulation to afford fused [5:7] oxazepanone γ-lactams

  摘要：

  DOI：

  10.24820/ark.5550190.p011.618
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 甲胺 、 sodium 1,4-diethoxy-1,4-dioxobut-2-en-2-olate 以 乙醇 、 水 为溶剂， 反应 1.0h， 以40%的产率得到ethyl 4-hydroxy-2-(4-methoxyphenyl)-1-methyl-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  一些 2-oxo-5-aryl-3-hydrazone 和 2-oxo-5-aryl-4-hydrazone pyrrolidine 衍生物的合成和生物活性

  摘要：

  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。

  DOI：

  10.3998/ark.5550190.0012.932

文献信息

• A Facile Synthesis of Pyrrolidine-Based Iminosugars as Potential Alpha-Glucosidase Inhibitors
  作者：Muhamad Zulfaqar Bacho、Mohd Fazli Mohammat、Zurina Shaameri、Agustono Wibowo、Firdaus Kamarulzaman、Ahmad Sazali Hamzah

  DOI：10.13005/ojc/360214

  日期：2020.4.28

  stereoselective reduction reactions was used to synthesize new pyrrolidine-based iminosugars. The key step of this strategy involves the contruction of a highly functionalised pyrroldine ring skeleton through MCR approach. Subsequently, amination and reduction reactions to the ring skeleton provide a quick access to new pyrrolidine-based imino sugars. The iminosugars were then tested against alpha glucosidase

  包含MCR（多组分反应），胺化反应和立体选择性还原反应的多方面方法用于合成新的吡咯烷基亚氨基糖。该策略的关键步骤涉及通过MCR方法构建高度官能化的吡咯烷环骨架。随后，对环骨架的胺化和还原反应可快速获得新的基于吡咯烷的亚氨基糖。然后测试亚氨基糖的α-葡糖苷酶活性，其中发现一种化合物（4-（（4-甲氧基苯基）氨基）吡咯烷丁-3-醇）在低剂量下最有效。
• 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。
• Facile Reduction of β-Enamino Oxopyrrolidine Carboxylates Mediated by Heterogeneous Palladium Catalyst
  作者：F. N. A. Abdul Rashid、M. F. Mohammat、F. E. Bouchamma、Z. Shaameri、A. S. Hamzah

  DOI：10.1134/s1070428020060184

  日期：2020.6

  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.