benzyl 2-(5-bromo-2-pyridyl)acetate

• 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: benzyl 2-(5-bromo-2-pyridyl)acetate
• 英文别名: benzyl 2'-(5-bromo)pyridylacetate；Benzyl 2-(5-bromopyridin-2-yl)acetate
• 化学式: C₁₄H₁₂BrNO₂
• 分子量: 306.159
• InChiKey: KAQQTVDDDMKCBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl 2-(5-bromo-2-pyridyl)acetate 在 四(三苯基膦)钯 、 sodium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 12.0h， 生成 (E)-3-(2-Bromo-phenyl)-3-hydroxy-2-(5-phenyl-pyridin-2-yl)-acrylic acid benzyl ester
  参考文献：
  名称：

  Solid phase synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins

  摘要：

  A solid phase strategy has been developed for the synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins. The key transformation is an intramolecular ipso substitution reaction which forms the coumarin heterocycle and culminates with cleavage of product from the polymer support. The pyridine moiety at C3 can be further modified with Suzuki coupling. A sample library with two diversity elements has been synthesized to demonstrate this ipso substation-based cyclo-elimination strategy. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.069

文献信息

• Ipso Substitution as a Route to Benzo[<i>c</i>]quinolizines and 4-Hydroxycoumarins
  作者：Yannan Liu、Mark J. Kurth

  DOI：10.1021/jo0161126

  日期：2002.4.1

  A convenient ipso substitution method for the preparation of benzo[c]quinolizine (2) and 4-hydroxy-3-(2'-pyridyl)coumarin (3) has been developed. The intramolecular nucleophilic substitution reaction of 3-oxo-2-(2'-pyridyl)-(2-halophenyl)propanoate (1) in refluxing xylenes gives initially benzo[c]quinolizine, while further heating results in the formation of 4-hydroxycoumarin. A mechanism has been

  开发了一种方便的ipso取代方法，用于制备苯并[c]喹啉嗪（2）和4-羟基-3-（2'-吡啶基）香豆素（3）。3-氧代-2-（2'-吡啶基）-（2-卤代苯基）丙酸酯（1）在回流二甲苯中的分子内亲核取代反应最初产生苯并[c]喹啉嗪，而进一步加热导致形成4-羟基香豆素。已经提出了一种机制来合理化两个竞争性反应途径，并讨论了HCl的作用。在最佳条件下，以中等至良好的产率制备了七个苯并[c]喹啉嗪和五个香豆素。
• Solid phase synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins
  作者：Yannan Liu、Aaron D. Mills、Mark J. Kurth

  DOI：10.1016/j.tetlet.2006.01.069

  日期：2006.3

  A solid phase strategy has been developed for the synthesis of 3-(5-arylpyridin-2-yl)-4-hydroxycoumarins. The key transformation is an intramolecular ipso substitution reaction which forms the coumarin heterocycle and culminates with cleavage of product from the polymer support. The pyridine moiety at C3 can be further modified with Suzuki coupling. A sample library with two diversity elements has been synthesized to demonstrate this ipso substation-based cyclo-elimination strategy. (c) 2006 Elsevier Ltd. All rights reserved.