6-(4-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)-3-((E)-1-(methoxycarbonyl)-2-methoxyvinyl) phenyl)hexanoic acid | 1266105-07-0

• 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: 6-(4-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)-3-((E)-1-(methoxycarbonyl)-2-methoxyvinyl) phenyl)hexanoic acid
• 英文别名: 6-[4-[6-(2-cyanophenoxy)pyrimidin-4-yl]oxy-3-[(E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]phenyl]hexanoic acid
• CAS: 1266105-07-0
• 化学式: C₂₈H₂₇N₃O₇
• 分子量: 517.538
• InChiKey: ORFMGZWKGMAHED-OQKWZONESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  tert-butyl hex-5-ynoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 10% palladium on activated carbon 、 氢气 、 caesium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 85.0 ℃ 、405.33 kPa 条件下， 反应 27.33h， 生成 6-(4-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)-3-((E)-1-(methoxycarbonyl)-2-methoxyvinyl) phenyl)hexanoic acid
  参考文献：
  名称：

  Concise and modular synthesis of regioisomeric haptens for the production of high-affinity and stereoselective antibodies to the strobilurin azoxystrobin

  摘要：

  The immune response to regioisomeric haptens of azoxystrobin with varied derivatization sites was studied. Based on the Sonogashira and Suzuki-Miyaura couplings and following a straightforward modular design, we have synthesized four haptens with the same linker anchored through C-C bonds and located at different sites of the molecule. The most stereoselective antibodies were produced from immunogens with the spacer arm at a distal position from the beta-methoxyacrylate moiety characteristic of strobilurins. Moreover, we observed that assay cross-reactivity was reliant on the functionalization site of the competitor derivative. Finally, the antibody binding site was explored using synthetic chemical analogues. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2010.11.054

文献信息

• Concise and modular synthesis of regioisomeric haptens for the production of high-affinity and stereoselective antibodies to the strobilurin azoxystrobin
  作者：Javier Parra、Josep V. Mercader、Consuelo Agulló、Antonio Abad-Fuentes、Antonio Abad-Somovilla

  DOI：10.1016/j.tet.2010.11.054

  日期：2011.1

  The immune response to regioisomeric haptens of azoxystrobin with varied derivatization sites was studied. Based on the Sonogashira and Suzuki-Miyaura couplings and following a straightforward modular design, we have synthesized four haptens with the same linker anchored through C-C bonds and located at different sites of the molecule. The most stereoselective antibodies were produced from immunogens with the spacer arm at a distal position from the beta-methoxyacrylate moiety characteristic of strobilurins. Moreover, we observed that assay cross-reactivity was reliant on the functionalization site of the competitor derivative. Finally, the antibody binding site was explored using synthetic chemical analogues. (C) 2010 Published by Elsevier Ltd.