tert-butyl 6-((E)-2-(methoxycarbonyl)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl) vinyloxy)hexanoate | 1266105-30-9

• 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: tert-butyl 6-((E)-2-(methoxycarbonyl)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl) vinyloxy)hexanoate
• CAS: 1266105-30-9
• 化学式: C₃₁H₃₃N₃O₇
• 分子量: 559.619
• InChiKey: GXTHKBKGIIOYPN-HIXSDJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  129.86
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-((E)-2-(methoxycarbonyl)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl) vinyloxy)hexanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以92%的产率得到6-((E)-2-(methoxycarbonyl)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl)vinyloxy) 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
• 作为产物：
  描述：

  2-苄氧基苯硼酸 在 potassium phosphate 、 四(三苯基膦)钯 、 10% palladium on activated carbon 、 氢气 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 13.75h， 生成 tert-butyl 6-((E)-2-(methoxycarbonyl)-2-(2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl) vinyloxy)hexanoate
  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