3,5-Dibromo-4-propylpyridine | 177273-34-6

• 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: 3,5-Dibromo-4-propylpyridine
• CAS: 177273-34-6
• 化学式: C₈H₉Br₂N
• 分子量: 278.974
• InChiKey: HFWUSLXQZLDJNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-Dibromo-4-propylpyridine 在 三乙胺 、 间氯过氧苯甲酸 、 copper(I) bromide 作用下， 以 甲醇 、 氯仿 、 乙腈 为溶剂， 反应 24.0h， 生成 3,5-Dimethoxy-4-propyl-pyridine-2-carbonitrile
  参考文献：
  名称：

  Studies towards the conception of new selective PPARβ/δ ligands

  摘要：

  In order to define new PPAR beta/delta ligands, SAR study on the selective PPAR beta/delta activator L-165,041 led to the identification of one key functional group for selective PPAR beta/delta activation. Further-more, taking advantage of SAR studies done elsewhere on the most selective PPAR beta/delta ligand GW501516, the conception of new ligands showing good affinity for PPAR beta/delta is reported. Finally, synthesis and biological evaluation of pyridine analogues have shown the benefical effect of the pyridine ring on the PPAR beta/ delta subtype selectivity. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.06.028
• 作为产物：
  描述：

  3,5-二溴吡啶 、 1-碘代丙烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以74%的产率得到3,5-Dibromo-4-propylpyridine
  参考文献：
  名称：

  Studies towards the conception of new selective PPARβ/δ ligands

  摘要：

  In order to define new PPAR beta/delta ligands, SAR study on the selective PPAR beta/delta activator L-165,041 led to the identification of one key functional group for selective PPAR beta/delta activation. Further-more, taking advantage of SAR studies done elsewhere on the most selective PPAR beta/delta ligand GW501516, the conception of new ligands showing good affinity for PPAR beta/delta is reported. Finally, synthesis and biological evaluation of pyridine analogues have shown the benefical effect of the pyridine ring on the PPAR beta/ delta subtype selectivity. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.06.028

文献信息

• [EN] INHIBITORS OF LOW MOLECULAR WEIGHT PROTEIN TYROSINE PHOSPHATASE (LMPTP) AND USES THEREOF<br/>[FR] INHIBITEURS DE LA PROTÉINE TYROSINE PHOSPHATASE DE FAIBLE POIDS MOLÉCULAIRE (LMPTP) ET LEURS UTILISATIONS
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2021003398A1

  公开（公告）日：2021-01-07

  Protein tyrosine phosphatases (PTPs) are key regulators of metabolism and insulin signaling. As a negative regulator of insulin signaling, the low molecular weight protein tyrosine phosphatase (LMPTP) is a target for insulin resistance and related conditions. Described herein are compounds capable of modulating the level of activity of LMPTP, compositions, and methods of using these compounds and compositions.

  蛋白酪氨酸磷酸酶（PTPs）是代谢和胰岛素信号传导的关键调节因子。作为胰岛素信号传导的负调节因子，低分子量蛋白酪氨酸磷酸酶（LMPTP）是胰岛素抵抗和相关疾病的靶点。本文描述了能够调节LMPTP活性水平的化合物、组合物以及使用这些化合物和组合物的方法。
• Synthesis of 4-alkyl-3,5-dibromo-, 3-bromo-4,5-dialkyl- and 3,4,5-trialkylpyridines via sequential metalation and metal-halogen exchange of 3,5-dibromopyridine
  作者：Yu Gui Gu、Erol K. Bayburt

  DOI：10.1016/0040-4039(96)00331-0

  日期：1996.4

  Lithiation of 3,5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3,5-dibromopyridines 2 in high yield. 3-Bromo-4,5-dialkylpyridines 3 were synthesized by metal-halogen exchange of 2 with one equivalent n-BuLi and reaction with a second electrophile. Further metal-halogen exchange of 3 and reaction with a third electrophile provided 3,4,5-trisubstituted pyridines

  3，5-二溴吡啶与LDA的锂化以及随后与亲电试剂的反应以高收率提供了4-烷基-3，5-二溴吡啶2。3-溴-4,5- dialkylpyridines 3通过金属-卤素交换合成2用一级当量的n-BuLi并反应与第二电试剂。的另外的金属-卤素交换3和反应与第三电子试剂提供3,4,5-三取代的吡啶4。