methyl 4-(4-bromophenyl)-5-cyano-6-methoxy-2-methylnicotinate | 1357618-17-7

• 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 4-(4-bromophenyl)-5-cyano-6-methoxy-2-methylnicotinate
• 英文别名: Methyl 4-(4-bromophenyl)-5-cyano-6-methoxy-2-methylpyridine-3-carboxylate
• CAS: 1357618-17-7
• 化学式: C₁₆H₁₃BrN₂O₃
• 分子量: 361.195
• InChiKey: PHTLZPSNVJDHLC-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  480.8±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-辛炔 、 methyl 4-(4-bromophenyl)-5-cyano-6-methoxy-2-methylnicotinate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以75%的产率得到methyl 5-cyano-6-methoxy-2-methyl-4-(4-(oct-1-yn-1-yl)phenyl)nicotinate
  参考文献：
  名称：

  Montmorillonite K-10 mediated green synthesis of cyano pyridines: Their evaluation as potential inhibitors of PDE4

  摘要：

  An efficient and green synthesis of functionalized cyano pyridines has been achieved via montmorillonite K-10 mediated multi-component reaction in a chemo- and regioselective manner. The four-component reaction of beta-keto ester, arylaldehyde, malononitrile and an alcohol provided a variety of pyridine derivatives and montmorillonite K-10 was found to be a reusable catalyst. The potential of this operationally simple methodology has been demonstrated in further structure elaboration of a compound synthesized via C C bond forming reactions under Suzuki, Sonogashira and Heck conditions. Some of the cyano pyridines synthesized showed PDE4B inhibitory properties in vitro and good interactions with PDE4B protein in silico suggesting cyano pyridine scaffold as a potential template for the discovery of novel PDE4 inhibitors. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.024
• 作为产物：
  描述：

  甲醇 、 乙酰乙酸甲酯 、 对溴苯甲醛 、 丙二腈 在 montmorillonite K-10 作用下， 反应 0.17h， 以85%的产率得到methyl 4-(4-bromophenyl)-5-cyano-6-methoxy-2-methylnicotinate
  参考文献：
  名称：

  Montmorillonite K-10 mediated green synthesis of cyano pyridines: Their evaluation as potential inhibitors of PDE4

  摘要：

  An efficient and green synthesis of functionalized cyano pyridines has been achieved via montmorillonite K-10 mediated multi-component reaction in a chemo- and regioselective manner. The four-component reaction of beta-keto ester, arylaldehyde, malononitrile and an alcohol provided a variety of pyridine derivatives and montmorillonite K-10 was found to be a reusable catalyst. The potential of this operationally simple methodology has been demonstrated in further structure elaboration of a compound synthesized via C C bond forming reactions under Suzuki, Sonogashira and Heck conditions. Some of the cyano pyridines synthesized showed PDE4B inhibitory properties in vitro and good interactions with PDE4B protein in silico suggesting cyano pyridine scaffold as a potential template for the discovery of novel PDE4 inhibitors. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.12.024

文献信息

• Montmorillonite K-10 mediated green synthesis of cyano pyridines: Their evaluation as potential inhibitors of PDE4
  作者：T. Ram Reddy、G. Rajeshwar Reddy、L. Srinivasula Reddy、Subbarao Jammula、Y. Lingappa、Ravikumar Kapavarapu、Chandana Lakshmi T. Meda、Kishore V.L. Parsa、Manojit Pal

  DOI：10.1016/j.ejmech.2011.12.024

  日期：2012.2

  An efficient and green synthesis of functionalized cyano pyridines has been achieved via montmorillonite K-10 mediated multi-component reaction in a chemo- and regioselective manner. The four-component reaction of beta-keto ester, arylaldehyde, malononitrile and an alcohol provided a variety of pyridine derivatives and montmorillonite K-10 was found to be a reusable catalyst. The potential of this operationally simple methodology has been demonstrated in further structure elaboration of a compound synthesized via C C bond forming reactions under Suzuki, Sonogashira and Heck conditions. Some of the cyano pyridines synthesized showed PDE4B inhibitory properties in vitro and good interactions with PDE4B protein in silico suggesting cyano pyridine scaffold as a potential template for the discovery of novel PDE4 inhibitors. (C) 2011 Elsevier Masson SAS. All rights reserved.