5-(4-氯苯基)烟酸乙酯 | 1258269-08-7

• 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
• 中文名称: 5-(4-氯苯基)烟酸乙酯
• 英文名称: Ethyl 5-(4-chlorophenyl)nicotinate
• 英文别名: ethyl 5-(4-chlorophenyl)pyridine-3-carboxylate
• CAS: 1258269-08-7
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: NIALGMCPMKETDW-UHFFFAOYSA-N

物化性质

• 沸点：
  394.1±32.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 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：

  5-(4-氯苯基)烟酸乙酯 在 水 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 5-(4-氯苯基)-3-吡啶羧酸
  参考文献：
  名称：

  Subtype-selective Nav1.8 sodium channel blockers: Identification of potent, orally active nicotinamide derivatives

  摘要：

  A series of aryl-substituted nicotinamide derivatives with selective inhibitory activity against the Na(v)1.8 sodium channel is reported. Replacement of the furan nucleus and homologation of the anilide linker in subtype-selective blocker A-803467 (1) provided potent, selective derivatives with improved aqueous solubility and oral bioavailability. Representative compounds from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.121
• 作为产物：
  描述：

  5-溴烟酸乙酯 、 4-氯苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以92%的产率得到5-(4-氯苯基)烟酸乙酯
  参考文献：
  名称：

  Extending the versatility of the Hemetsberger–Knittel indole synthesis through microwave and flow chemistry

  摘要：

  Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.066

文献信息

• Subtype-selective Nav1.8 sodium channel blockers: Identification of potent, orally active nicotinamide derivatives
  作者：Michael E. Kort、Robert N. Atkinson、James B. Thomas、Irene Drizin、Matthew S. Johnson、Matthew A. Secrest、Robert J. Gregg、Marc J.C. Scanio、Lei Shi、Ahmed H. Hakeem、Mark A. Matulenko、Mark L. Chapman、Michael J. Krambis、Dong Liu、Char-Chang Shieh、XuFeng Zhang、Gricelda Simler、Joseph P. Mikusa、Chengmin Zhong、Shailen Joshi、Prisca Honore、Rosemarie Roeloffs、Stephen Werness、Brett Antonio、Kennan C. Marsh、Connie R. Faltynek、Douglas S. Krafte、Michael F. Jarvis、Brian E. Marron

  DOI：10.1016/j.bmcl.2010.08.121

  日期：2010.11

  A series of aryl-substituted nicotinamide derivatives with selective inhibitory activity against the Na(v)1.8 sodium channel is reported. Replacement of the furan nucleus and homologation of the anilide linker in subtype-selective blocker A-803467 (1) provided potent, selective derivatives with improved aqueous solubility and oral bioavailability. Representative compounds from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.
• Extending the versatility of the Hemetsberger–Knittel indole synthesis through microwave and flow chemistry
  作者：Nadeesha Ranasinghe、Graham B. Jones

  DOI：10.1016/j.bmcl.2013.01.066

  日期：2013.3

  Microwave, flow and combination methodologies have been applied to the synthesis of a number of substituted indoles. Based on the Hemetsberger-Knittel (HK) process, modifications allow formation of products rapidly and in high yield. Adapting the methodology allows formation of 2-unsubstituted indoles and derivatives, and a route to analogs of the antitumor agent PLX-4032 is demonstrated. The utility of the HK substrates is further demonstrated through bioconjugation and subsequent ring closure and via Huisgen type [3+2] cycloaddition chemistry, allowing formation of peptide adducts which can be subsequently labeled with fluorine tags. (C) 2013 Elsevier Ltd. All rights reserved.