tert-butyl 6-(4,6-dichloropyrimidin-2-yl)hex-5-ynoate | 1266105-17-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: tert-butyl 6-(4,6-dichloropyrimidin-2-yl)hex-5-ynoate
• 英文别名: Tert-butyl 6-(4,6-dichloropyrimidin-2-yl)hex-5-ynoate
• CAS: 1266105-17-2
• 化学式: C₁₄H₁₆Cl₂N₂O₂
• 分子量: 315.199
• InChiKey: GDTJGZNVMBJMFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 6-(4,6-dichloropyrimidin-2-yl)hex-5-ynoate 在 10% palladium on activated carbon 、 氢气 、 caesium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 21.5h， 生成 tert-butyl 6-(4-chloro-6-(2-((E)-1-(methoxycarbonyl)-2-methoxyvinyl)phenoxy)pyrimidin-2-yl)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：

  4,6-dichloro-2-iodopyrimidine 、 tert-butyl hex-5-ynoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以73%的产率得到tert-butyl 6-(4,6-dichloropyrimidin-2-yl)hex-5-ynoate
  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