2-bromo-N-(4-fluorophenyl)-N-methylpropanamide | 1283551-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-N-(4-fluorophenyl)-N-methylpropanamide
• CAS: 1283551-73-4
• 化学式: C₁₀H₁₁BrFNO
• 分子量: 260.106
• InChiKey: HMBOPZTWTLUXDP-UHFFFAOYSA-N

物化性质

• 沸点：
  304.9±27.0 °C(Predicted)
• 密度：
  1.483±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(4-fluorophenyl)-N-methylpropanamide 在 potassium phosphate 、 四(三苯基膦)镍 、 1,3-双(二苯基膦)丙烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以56%的产率得到5-fluoro-1,3-dimethylindolin-2-one
  参考文献：
  名称：

  Nickel-Catalyzed Aromatic C–H Alkylation with Secondary or Tertiary Alkyl–Bromine Bonds for the Construction of Indolones

  摘要：

  A nickel-catalyzed aromatic C-H alkylation with tertiary or secondary alkyl-Br bonds for the construction of indolones was demonstrated. Various functional groups were well tolerated. Moreover, the challenging secondary alkyl bromides were well introduced in this transformation. Radical trapping and photocatalysis conditions exhibited that it is most likely to be a radical process for this aromatic C-H alkylation.

  DOI：

  10.1021/ol403021p
• 作为产物：
  描述：

  4-氟-N-甲基苯胺 、 2-溴丙酰氯 在 potassium hydroxide 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 1.5h， 以88%的产率得到2-bromo-N-(4-fluorophenyl)-N-methylpropanamide
  参考文献：
  名称：

  Translocator protein ligands based on N -methyl-(quinolin-4-yl)oxypropanamides with properties suitable for PET radioligand development

  摘要：

  Modifications to an N-methyl-(quinolin-4-yl)oxypropanamide scaffold were explored to discover leads for developing new radioligands for PET imaging of brain TSPO (translocator protein), a biomarker of neuroinfiammation. Whereas contraction of the quinolinyl portion of the scaffold or cyclization of the tertiary amido group abolished high TSPO affinity, insertion of an extra nitrogen atom into the 2-arylquinolinyl portion was effective in retaining sub-nanomolar affinity for rat TSPO, while also decreasing lipophilicity to within the moderate range deemed preferable for a PET radioligand. Replacement of a phenyl group on the amido nitrogen with an isopropyl group was similarly effective. Among others, compound 20 (N-methyl-N-phenyl-2-[2-(pyridin-2-yl)-1,8-naphthyridin-4-yloxy]propanamide) appears especially appealing for PET radioligand development, based on high selectivity and high affinity (K-i = 0.5 nM) for rat TSPO, moderate lipophilicity (logD = 2.48), and demonstrated amenability to labeling with carbon-11. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2016.08.046

文献信息

• 含氮杂环化合物、标记的含氮杂环化合物及其制备方法和应用
  申请人：暨南大学

  公开号：CN114085221B

  公开（公告）日：2022-12-09

  本发明涉及一种含氮杂环化合物、标记的含氮杂环化合物及其制备方法和应用。该含氮杂环化合物为上述含氮杂环化合物可应用于制备靶向转位蛋白的试剂。
• 靶向转位蛋白TSPO的新型正电子药物[
  申请人：暨南大学附属第一医院（广州华侨医院）

  公开号：CN114075167B

  公开（公告）日：2022-11-22

  本发明涉及靶向转位蛋白TSPO的新型正电子药物[18F]TPO1开发，本发明设计开发了新型的TSPO配体TPO1，并利用18F及螺环高价碘叶立德前体Pre1实现了标记，合成了新型TSPO靶向型正电子药物[18F]TPO1；通过经过基因测序的人脑脑片实施体外放射自显影，结果显示该药物的特异性较高，且对rs6971的敏感度较弱；同时，大鼠活体PET动态扫描结果显示，该探针可以通过血脑屏障。
• 10.1021/jacs.4c03745
  作者：Pan, Qi、Wang, Kuai、Xu, Weipeng、Ai, Yuqi、Ping, Yuanyuan、Liu, Chuhan、Wang, Minyan、Zhang, Junliang、Kong, Wangqing

  DOI：10.1021/jacs.4c03745

  日期：——

  oxindoles containing 1,3-nonadjacent stereocenters were obtained with high levels of enantio- and diastereoselectivity. Mechanistic experiments and density functional theory calculations indicate that magnesium salt plays a key role in controlling the diastereoselectivity. Furthermore, another set of complementary stereoisomeric products were constructed from the same set of starting materials using Ph-Phox

  与具有单个立体中心或1,2-相邻立体中心的分子的不对称合成相比，通过单一催化剂以对映选择性和非对映选择性方式同时构建无环1,3-非相邻立体中心仍然是一个艰巨的挑战。在这里，我们展示了通过镍催化的烯烃系芳基溴化物和α-溴酰胺的还原环化/交叉偶联来构建1,3-不相邻立体中心的对映选择性和非对映发散结构，这代表了烯烃环化/双官能化的主要剩余立体化学挑战。使用 Ming-Phos 作为配体，获得了一系列含有 1,3-不相邻立体中心的多种羟吲哚，具有高水平的对映选择性和非对映选择性。机理实验和密度泛函理论计算表明镁盐在控制非对映选择性方面起着关键作用。此外，使用 Ph-Phox 作为配体，从同一组起始材料构建了另一组互补的立体异构产物。
• Translocator protein ligands based on N -methyl-(quinolin-4-yl)oxypropanamides with properties suitable for PET radioligand development
  作者：Chad Brouwer、Kimberly J. Jenko、Sami S. Zoghbi、Cheryl L. Morse、Robert B. Innis、Victor W. Pike

  DOI：10.1016/j.ejmech.2016.08.046

  日期：2016.11

  Modifications to an N-methyl-(quinolin-4-yl)oxypropanamide scaffold were explored to discover leads for developing new radioligands for PET imaging of brain TSPO (translocator protein), a biomarker of neuroinfiammation. Whereas contraction of the quinolinyl portion of the scaffold or cyclization of the tertiary amido group abolished high TSPO affinity, insertion of an extra nitrogen atom into the 2-arylquinolinyl portion was effective in retaining sub-nanomolar affinity for rat TSPO, while also decreasing lipophilicity to within the moderate range deemed preferable for a PET radioligand. Replacement of a phenyl group on the amido nitrogen with an isopropyl group was similarly effective. Among others, compound 20 (N-methyl-N-phenyl-2-[2-(pyridin-2-yl)-1,8-naphthyridin-4-yloxy]propanamide) appears especially appealing for PET radioligand development, based on high selectivity and high affinity (K-i = 0.5 nM) for rat TSPO, moderate lipophilicity (logD = 2.48), and demonstrated amenability to labeling with carbon-11. Published by Elsevier Masson SAS.
• Nickel-Catalyzed Aromatic C–H Alkylation with Secondary or Tertiary Alkyl–Bromine Bonds for the Construction of Indolones
  作者：Chao Liu、Dong Liu、Wei Zhang、Liangliang Zhou、Aiwen Lei

  DOI：10.1021/ol403021p

  日期：2013.12.20

  A nickel-catalyzed aromatic C-H alkylation with tertiary or secondary alkyl-Br bonds for the construction of indolones was demonstrated. Various functional groups were well tolerated. Moreover, the challenging secondary alkyl bromides were well introduced in this transformation. Radical trapping and photocatalysis conditions exhibited that it is most likely to be a radical process for this aromatic C-H alkylation.