methyl 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate | 1426575-26-9

• 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 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
• CAS: 1426575-26-9
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: VBUWSTCQKNZKGG-UHFFFAOYSA-N

物化性质

• 密度：
  1.363±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate 在 喹啉 、 copper chromite 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.2h， 生成 5-(4-氯苯基)-1H-吡咯并[2,3-b]吡啶
  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
• 作为产物：
  描述：

  methyl 2-azido-3-[5-(4-chlorophenyl)pyridin-3-yl]prop-2-enoate 以 甲苯 为溶剂， 反应 0.2h， 以85%的产率得到methyl 5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
  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

• 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.