N-(4-bromophenyl)-3-morpholinopropanamide | 461400-41-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(4-bromophenyl)-3-morpholinopropanamide
• 英文别名: N-(4-bromophenyl)-3-morpholin-4-ylpropanamide
• CAS: 461400-41-9
• 化学式: C₁₃H₁₇BrN₂O₂
• 分子量: 313.194
• InChiKey: FFKILSHSSTVOBO-UHFFFAOYSA-N

物化性质

• 沸点：
  477.4±40.0 °C(Predicted)
• 密度：
  1.424±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-3-morpholinopropanamide 、 3-吡啶硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 18.0h， 以67%的产率得到3-morpholino-N-(4-(pyridin-3-yl)phenyl)propanamide
  参考文献：
  名称：

  Consequences of linker length alteration of the α7 nicotinic acetylcholine receptor (nAChR) agonist, SEN12333

  摘要：

  A series of ligands based on SEN12333, containing either contracted or elongated alkyl chains, were synthesized and evaluated in molecular docking studies against a homology model of the alpha 7 nicotinic acetylcholine receptor (nAChR) subtype. The predicted binding of all ligands was highly similar, with the exception of the analog containing a 5 methylene unit spacer. However, in vitro competition binding assays revealed that the ligands possessed dissimilar binding affinities, with a K-i range of more than an order of magnitude (K-i = 0.50 to >10 mu M), and only SEN12333 itself exhibited functional activity at the alpha 7 nAChR. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.02.052
• 作为产物：
  描述：

  4-溴苯胺 在 potassium carbonate 、 Selectfluor 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-(4-bromophenyl)-3-morpholinopropanamide
  参考文献：
  名称：

  无金属的C–S键裂解可得到N-取代的丙烯酰胺和β-氨基丙酰胺

  摘要：

  已经建立了无金属的C-S键裂解过程，可在Selectfluor存在下构建N取代的丙烯酰胺和β-氨基丙酰胺衍生物。

  DOI：

  10.1002/ejoc.201900960

文献信息

• LiCl-promoted amination of β-methoxy amides (γ-lactones)
  作者：Ru Zhao、Bing-Lin Zeng、Wen-Qiang Jia、Hong-Yi Zhao、Long-Ying Shen、Xiao-Jian Wang、Xian-Dao Pan

  DOI：10.1039/d0ra07170f

  日期：——

  An efficient and mild method has been developed for the amination of β-methoxy amides (γ-lactones) including natural products michelolide, costunolide and parthenolide derivatives by using lithium chloride in good yields. This reaction is applicable to a wide range of substrates with good functional group tolerance. Mechanism studies show that the reactions undergo a LiCl promoted MeOH elimination

  已经开发了一种高效温和的方法，用于以良好收率使用氯化锂胺化 β-甲氧基酰胺（γ-内酯），包括天然产物 michelolide、costunolide 和 parthenolide 衍生物。该反应适用于广泛的具有良好官能团耐受性的底物。机理研究表明，反应经历了 LiCl 促进的 MeOH 从底物中消除形成相应的 α,β-不饱和中间体，然后是胺的迈克尔加成。
• Consequences of linker length alteration of the α7 nicotinic acetylcholine receptor (nAChR) agonist, SEN12333
  作者：Corinne Beinat、Samuel D. Banister、Saundra van Prehn、Munikumar Reddy Doddareddy、David Hibbs、Michael Sako、Mary Chebib、Thao Tran、Nour Al-Muhtasib、Yingxian Xiao、Michael Kassiou

  DOI：10.1016/j.bmcl.2012.02.052

  日期：2012.4

  A series of ligands based on SEN12333, containing either contracted or elongated alkyl chains, were synthesized and evaluated in molecular docking studies against a homology model of the alpha 7 nicotinic acetylcholine receptor (nAChR) subtype. The predicted binding of all ligands was highly similar, with the exception of the analog containing a 5 methylene unit spacer. However, in vitro competition binding assays revealed that the ligands possessed dissimilar binding affinities, with a K-i range of more than an order of magnitude (K-i = 0.50 to >10 mu M), and only SEN12333 itself exhibited functional activity at the alpha 7 nAChR. (C) 2012 Elsevier Ltd. All rights reserved.
• Metal-Free C-S Bond Cleavage to Access <i>N</i> -Substituted Acrylamide and β-Aminopropanamide
  作者：Ke Yang、Yi Li、Zhiyan Ma、Long Tang、Yue Yin、Hao Zhang、Zhengyi Li、Xiaoqiang Sun

  DOI：10.1002/ejoc.201900960

  日期：2019.9.8

  The metal‐free C–S bond cleavage process has been established to construct N‐substituted acrylamide and β‐aminopropanamide derivatives in the presence of Selectfluor.

  已经建立了无金属的C-S键裂解过程，可在Selectfluor存在下构建N取代的丙烯酰胺和β-氨基丙酰胺衍生物。