ethyl 1-butyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate | 4563-89-7

• 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: ethyl 1-butyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: ethyl 1-butyl-4-hydroxy-5-oxo-2H-pyrrole-3-carboxylate
• CAS: 4563-89-7
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: DXTWHAVRIJHSNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  ethyl 1-butyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate 在 ammonium acetate 、 溶剂黄146 作用下， 以88%的产率得到4-氨基-1-丁基-5-氧代-2,5-二氢-1H-吡咯-3-羧酸乙酯
  参考文献：
  名称：

  Discovery of novel pyrrole derivatives as potent agonists for the niacin receptor GPR109A

  摘要：

  Novel pyrrole derivatives were discovered as potent agonists of the niacin receptor, GPR109A. During the derivatization, compound 16 was found to be effective both in vitro and in vivo. The compound 16 exhibited a significant reduction of the non-esterified fatty acid in human GPR109A transgenic rats, and the duration of its in vivo efficacy was much longer than niacin.

  DOI：

  10.1016/j.bmcl.2020.127105
• 作为产物：
  描述：

  N-(正丁基)-b-氨基丙酸乙酯 、 草酸二乙酯 在 sodium ethanolate 作用下， 生成 ethyl 1-butyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Nguyen, Van-Ha; Nishino, Hiroshi; Kurosawa, Kazu, Heterocycles, 1998, vol. 48, # 3, p. 465 - 480

  摘要：

  DOI：

文献信息

• Palladium-catalyzed hydrogenolysis of azabicyclic peroxides. Quantitative transformation to 1-hydroxy-7-aza-2-oxabicyclo[3.3.0]octanes
  作者：Firoz Alam Chowdhury、Shougo Kajikawa、Hiroshi Nishino、Kazu Kurosawa

  DOI：10.1016/s0040-4039(99)00604-8

  日期：1999.5

  The palladium-catalyzed reduction of 1-hydroxy-8-aza-2,3-dioxabicyclo[4.3.0]nonanes, which were readily obtained by the manganese(III)-mediated oxidative formal [2+2+2] cycloaddition of pyrrolidinedione derivatives with alkenes and molecular oxygen, led to formal extrusion of one of the peroxide oxygens and produced 1-hydroxy-7-aza-2-oxabicyclo[3.3.0]octanes in quantitative chemical yields.

  钯催化的1-羟基-8-氮杂-2,3-二氧杂双环[4.3.0]壬烷的钯催化还原反应很容易通过吡咯烷二酮的锰（III）介导的氧化式[2 + 2 + 2]环加成反应获得与烯烃和分子氧的衍生物导致过氧化物氧之一的正式挤出，并以定量的化学收率产生了1-羟基-7-氮杂-2-氧杂双环[3.3.0]辛烷。
• 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。