3-Oxo-5-pyridin-4-yl-pentanoic acid ethyl ester | 873917-47-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 3-Oxo-5-pyridin-4-yl-pentanoic acid ethyl ester
• CAS: 873917-47-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: GJCWYXPFRPOCHN-UHFFFAOYSA-N

物化性质

• 沸点：
  334.1±22.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  56.26
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-Oxo-5-pyridin-4-yl-pentanoic acid ethyl ester 在 lithium hydroxide 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 4-(2-pyridin-4-yl-ethyl)-thiazole-5-carboxylic acid (4-chloro-phenyl)-amide
  参考文献：
  名称：

  N-(Aryl)-4-(azolylethyl)thiazole-5-carboxamides: Novel potent inhibitors of VEGF receptors I and II

  摘要：

  Novel potent derivatives of N-(aryl)-4-(azolylethyl)thiazole-5-carboxamides are described as inhibitors of vascular endothelial growth factor receptor 11 (VEGFR-2). Several compounds display VEGFR-2 inhibitory activity reaching IC50 < 100 nM in both enzymatic and cellular assays. The compounds also inhibit the related tyrosine kinase, VEGFR-1. By controlling the substitution pattern on the 5-carboxamido pharmacophore, both dual and specific VEGFR-2 thiazoles were identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.058
• 作为产物：
  描述：

  4-甲基吡啶 、 4-氯乙酰乙酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 3-Oxo-5-pyridin-4-yl-pentanoic acid ethyl ester
  参考文献：
  名称：

  N-(Aryl)-4-(azolylethyl)thiazole-5-carboxamides: Novel potent inhibitors of VEGF receptors I and II

  摘要：

  Novel potent derivatives of N-(aryl)-4-(azolylethyl)thiazole-5-carboxamides are described as inhibitors of vascular endothelial growth factor receptor 11 (VEGFR-2). Several compounds display VEGFR-2 inhibitory activity reaching IC50 < 100 nM in both enzymatic and cellular assays. The compounds also inhibit the related tyrosine kinase, VEGFR-1. By controlling the substitution pattern on the 5-carboxamido pharmacophore, both dual and specific VEGFR-2 thiazoles were identified. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.058

文献信息

• Titanium-Mediated Spirocyclization Reactions of 4-Alkylpyridines
  作者：Sharavathi G. Parameswarappa、F. Christopher Pigge

  DOI：10.1021/ol1012636

  日期：2010.8.6

  Pyridines substituted at the 4-position with alkyl tethers containing beta-dicarbonyl moieties were converted to spirocyclic 4,4-disubstituted dihydropyridines. Optimal conditions for these transformations involved N-acylation of the pyridine substrate with a chloroformate electrophile in the presence of Ti((OPr)-Pr-i)(4). Cyclization products could be easily converted into spiro-piperidine derivatives or elaborated into more complex heterocyclic frameworks via Au-catalyzed cycloisomerization.