ethyl 2-methyl-5-(pyridin-2-yl)furan-3-carboxylate | 1334598-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: ethyl 2-methyl-5-(pyridin-2-yl)furan-3-carboxylate
• 英文别名: Ethyl 2-methyl-5-pyridin-2-ylfuran-3-carboxylate
• CAS: 1334598-88-7
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: LNWGKSWQUKEZKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.33
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-5-(pyridin-2-yl)furan-3-carboxylate 在 水 、 lithium hydroxide 作用下， 以 甲醇 为溶剂， 以90%的产率得到2-methyl-5-pyridin-2-ylfuran-3-carboxylic acid
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

  摘要：

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.128
• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 0.25h， 以41%的产率得到ethyl 2-methyl-5-(pyridin-2-yl)furan-3-carboxylate
  参考文献：
  名称：

  Discovery and hit-to-lead optimization of novel allosteric glucokinase activators

  摘要：

  We report on a hit generation and hit-to-lead program of a novel class of glucokinase activators (GKAs). Hit compounds, activators at low glucose concentration only were identified by vHTS. Scaffold modification reliably afforded activators also at high substrate level. Potency was increased by introduction of a hydrogen bond acceptor as proposed by molecular docking. Replacement of the initial alkylene linkers with a rigid 1,2-phenylene motif followed by further studies eventually furnished a series of potent lead compounds exhibiting steep SAR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.128

文献信息

• Regioselective Synthesis of Multisubstituted Furans via Metalloradical Cyclization of Alkynes with α-Diazocarbonyls: Construction of Functionalized α-Oligofurans
  作者：Xin Cui、Xue Xu、Lukasz Wojtas、Martin M. Kim、X. Peter Zhang

  DOI：10.1021/ja309446n

  日期：2012.12.12

  five-membered furan structures. The Co(II) complex of 3,5-Di(t)Bu-IbuPhyrin, [Co(P1)], is effective in catalyzing the metalloradical cyclization reaction under neutral and mild conditions. The [Co(P1)]-catalyzed process tolerates a wide range of α-diazocarbonyls and terminal alkynes with varied steric and electronic properties, producing polyfunctionalized furans with complete regioselectivity. The catalytic

  由 Co(II)-卟啉配合物活化 α-重氮羰基产生的 Co(III)-卡宾自由基已被证明与炔烃发生新型串联自由基加成反应，提供五元呋喃结构。3,5-Di(t)Bu-IbuPhyrin 的 Co(II) 配合物 [Co(P1)] 在中性和温和条件下可有效催化金属自由基环化反应。[Co(P1)] 催化的过程可以耐受各种具有不同空间和电子特性的 α-重氮羰基和末端炔烃，从而产生具有完全区域选择性的多官能化呋喃。催化合成具有高度的官能团耐受性，可以反复应用于构建功能化的α-低聚呋喃。