tert-butyl 6-(3-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)-4-(hydroxy)phenyl)hexanoate | 1266105-13-8

• 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-(3-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)-4-(hydroxy)phenyl)hexanoate
• 英文别名: tert-butyl 6-[3-[(E)-1,3-dimethoxy-3-oxoprop-1-en-2-yl]-4-hydroxyphenyl]hexanoate
• CAS: 1266105-13-8
• 化学式: C₂₁H₃₀O₆
• 分子量: 378.466
• InChiKey: DXGRXTZNRCSERQ-SAPNQHFASA-N

物化性质

• 沸点：
  507.0±50.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-(3-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)-4-(hydroxy)phenyl)hexanoate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 tert-butyl 6-(4-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)-3-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenyl)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
• 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 、 三乙胺 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~70.0 ℃ 、405.33 kPa 条件下， 反应 22.0h， 生成 tert-butyl 6-(3-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)-4-(hydroxy)phenyl)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

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.