methyl 3-benzyloxy-4-bromo-6-methylpicolinate | 1342906-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 3-benzyloxy-4-bromo-6-methylpicolinate
• 英文别名: Methyl 3-(benzyloxy)-4-bromo-6-methylpicolinate；methyl 4-bromo-6-methyl-3-phenylmethoxypyridine-2-carboxylate
• CAS: 1342906-72-2
• 化学式: C₁₅H₁₄BrNO₃
• 分子量: 336.185
• InChiKey: LVGHDUWLRJIZCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-hex-5-ynyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline 、 methyl 3-benzyloxy-4-bromo-6-methylpicolinate 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以32%的产率得到methyl 3-(benzyloxy)-4-(6-(6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinolin-2(1H)-yl)hex-1-ynyl)-6-methylpicolinate
  参考文献：
  名称：

  苯基四氢异喹啉-吡啶并肟作为抑制人乙酰胆碱酯酶脱磷酸作用的有效不带电活化剂。

  摘要：

  吡啶和双吡啶醛肟被用作解毒剂，以重新激活被有机磷神经毒剂抑制的乙酰胆碱酯酶（AChE）。在本文中，我们描述了一系列九种非季基苯基四氢异喹啉-吡啶并肟肟共轭物，它们比吡啶鎓肟更有效，或与吡啶肟肟一样有效，可以重新激活VX，塔邦和对氧磷抑制的人AChE。这项研究探索了这个新的活化剂家族的结构-活性关系，并表明1b - d是广泛的不带电荷的hAChE活化剂。

  DOI：

  10.1021/jm3015519
• 作为产物：
  描述：

  3-羟基-2-吡啶甲酸 在 四(三苯基膦)钯 、 硫酸 、 溴 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 82.0h， 生成 methyl 3-benzyloxy-4-bromo-6-methylpicolinate
  参考文献：
  名称：

  Straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals and agrochemicals

  摘要：

  A practical and rapid preparation of 3-benzyloxy-4-bromo and 3-benzyloxy-5-bromopicolinate esters 10 and 16 was developed in four steps, respectively, in 38% and 31% overall yield. Then their viability as partners for cross-coupling reactions has been evaluated in Suzuki-Miyaura, Hartwig-Buchwald, and Sonogashira reactions to synthesize biologically relevant targets. The preparation of these two highly functionalizable pyridines 10 and 16 has been never described to date in the literature and could be used as common building block for the preparation of several biologically active compounds or agrochemical products. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.024

文献信息

• Straightforward and efficient synthesis of 3-benzyloxy-4-bromopicolinate ester and 3-benzyloxy-5-bromopicolinate ester, common building blocks for pharmaceuticals and agrochemicals
  作者：Tristan Verdelet、Guillaume Mercey、Nobi Correa、Ludovic Jean、Pierre-Yves Renard

  DOI：10.1016/j.tet.2011.09.024

  日期：2011.11

  A practical and rapid preparation of 3-benzyloxy-4-bromo and 3-benzyloxy-5-bromopicolinate esters 10 and 16 was developed in four steps, respectively, in 38% and 31% overall yield. Then their viability as partners for cross-coupling reactions has been evaluated in Suzuki-Miyaura, Hartwig-Buchwald, and Sonogashira reactions to synthesize biologically relevant targets. The preparation of these two highly functionalizable pyridines 10 and 16 has been never described to date in the literature and could be used as common building block for the preparation of several biologically active compounds or agrochemical products. (C) 2011 Elsevier Ltd. All rights reserved.
• Phenyltetrahydroisoquinoline–Pyridinaldoxime Conjugates as Efficient Uncharged Reactivators for the Dephosphylation of Inhibited Human Acetylcholinesterase
  作者：Guillaume Mercey、Julien Renou、Tristan Verdelet、Maria Kliachyna、Rachid Baati、Emilie Gillon、Mélanie Arboléas、Mélanie Loiodice、Florian Nachon、Ludovic Jean、Pierre-Yves Renard

  DOI：10.1021/jm3015519

  日期：2012.12.13

  Pyridinium and bis-pyridinium aldoximes are used as antidotes to reactivate acetylcholinesterase (AChE) inhibited by organophosphorus nerve agents. Herein, we described a series of nine nonquaternary phenyltetrahydroisoquinoline–pyridinaldoxime conjugates more efficient than or as efficient as pyridinium oximes to reactivate VX-, tabun- and ethyl paraoxon-inhibited human AChE. This study explores the

  吡啶和双吡啶醛肟被用作解毒剂，以重新激活被有机磷神经毒剂抑制的乙酰胆碱酯酶（AChE）。在本文中，我们描述了一系列九种非季基苯基四氢异喹啉-吡啶并肟肟共轭物，它们比吡啶鎓肟更有效，或与吡啶肟肟一样有效，可以重新激活VX，塔邦和对氧磷抑制的人AChE。这项研究探索了这个新的活化剂家族的结构-活性关系，并表明1b - d是广泛的不带电荷的hAChE活化剂。