methyl 2-methyl-5-phenylpyridine-3-carboxylate | 63820-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 2-methyl-5-phenylpyridine-3-carboxylate
• 英文别名: 2-methyl-5-phenyl methylnicotinate；2-methyl-5-phenyl-nicotinic acid methyl ester；3-Methoxycarbonyl-2-methyl-5-phenylpyridin
• CAS: 63820-74-6
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: DCSKEGODHMWILA-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C(Solv: hexane (110-54-3))
• 沸点：
  134-136 °C(Press: 0.2 Torr)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-5-phenylpyridine-3-carboxylate 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 7-bromo-3-phenyl-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one
  参考文献：
  名称：

  Discovery of a 5H-Benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (MK-2461) Inhibitor of c-Met Kinase for the Treatment of Cancer

  摘要：

  c-Met is a transmembrane tyrosine kinase that mediates activation of several signaling pathways implicated in aggressive cancer phenotypes. In recent years, research into this area has highlighted c-Met as an attractive cancer drug target, triggering a number of approaches to disrupt aberrant c-Met signaling. Screening efforts identified a unique class of 5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one kinase inhibitors, exemplified by 1. Subsequent SAR studies led to the development of 81 (MK-2461), a potent inhibitor of c-Met that was efficacious in preclinical animal models of tumor suppression. In addition, biochemical studies and X-ray analysis have revealed that this unique class of kinase inhibitors binds preferentially to the activated (phosphorylated) form of the kinase. This report details the development of 81 and provides a description of its unique biochemical properties.

  DOI：

  10.1021/jm200112k
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 2-phenyl-1,3-bis(dimethylamino)trimethinium hexafluorophosphate 在 potassium tert-butylate 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 9.75h， 以60%的产率得到methyl 2-methyl-5-phenylpyridine-3-carboxylate
  参考文献：
  名称：

  A General Preparation of Pyridines and Pyridones via the Annulation of Ketones and Esters

  摘要：

  A general preparation of pyridines 4a-f from stabilized ketones 3a-c and aryl ketones 3d-f is described. The annulation of stabilized esters 3g,h gives access to the corresponding 2-pyridones 4g,h. The annulation reactions proceed in fair to excellent yields (46-87%) with vinamidinium hexafluorophosphate salts 2a-d containing electron-withdrawing groups at the beta -positisn. The mechanism of the reaction was investigated by NMR and proceeds through the formation of a dienaminone intermediate.

  DOI：

  10.1021/jo0155198

文献信息

• [EN] 5H-BENZO[4,5]CYCLOHEPTA[1,2-B]PYRIDINE NMDA/NR2B ANTAGONISTS<br/>[FR] ANTAGONISTES 5H-BENZO[4,5]CYCLOHEPTA[1,2-B]PYRIDINES DE NMDA/NR2B
  申请人：MERCK & CO INC

  公开号：WO2003084931A1

  公开（公告）日：2003-10-16

  Benzo [4,5]cyclohepta[1,2-b]pyridines represented by Formula (I): or pharmaceutically acceptable salts thereof, are effective as NMDA NR2B antagonists useful for relieving pain.

  Benzo[4,5]环庚[1,2-b]吡啶代表的化学式（I）：或其药学上可接受的盐，作为NMDA NR2B拮抗剂，对缓解疼痛有效。
• JUTZ C.; LOEBERING H.-G.; TRINKL K.-H., SYNTHESIS <SYNT-BF>, 1977, NO 5, 326-328
  作者：JUTZ C.、 LOEBERING H.-G.、 TRINKL K.-H.

  DOI：——

  日期：——