ethyl 2-(6-chloro-4-methylpyridin-3-yl)acetate | 1261771-82-7

• 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: ethyl 2-(6-chloro-4-methylpyridin-3-yl)acetate
• 英文别名: Ethyl 2-(6-chloro-4-methylpyridin-3-YL)acetate
• CAS: 1261771-82-7
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: LFYFBHWEKGKFJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  bromozinc(1+),ethyl acetate 、 2-氯-4-甲基-5-溴吡啶 在 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以71%的产率得到ethyl 2-(6-chloro-4-methylpyridin-3-yl)acetate
  参考文献：
  名称：

  A chemoselective Reformatsky–Negishi approach to α-haloaryl esters

  摘要：

  A practical synthesis of alpha-haloaryl esters has been achieved via a chemoselective Negishi coupling of poly-halogenated aromatics and Reformatsky reagents in the presence of catalytic Pd(dba)(2) and Xantphos. This chemistry tolerates a variety of aryl halides and was successfully applied to the synthesis of Ibuprofen. The alpha-haloaryl ester products, exemplified by ethyl 2-(4-bromo-2-chlorophenyl)acetate (3a), can be further functionalized via palladium or copper catalysis to afford an array of a-aryl esters. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.053

文献信息

• A chemoselective Reformatsky–Negishi approach to α-haloaryl esters
  作者：Brian Wong、Xin Linghu、James J. Crawford、Joy Drobnick、Wendy Lee、Haiming Zhang

  DOI：10.1016/j.tet.2013.12.053

  日期：2014.2

  A practical synthesis of alpha-haloaryl esters has been achieved via a chemoselective Negishi coupling of poly-halogenated aromatics and Reformatsky reagents in the presence of catalytic Pd(dba)(2) and Xantphos. This chemistry tolerates a variety of aryl halides and was successfully applied to the synthesis of Ibuprofen. The alpha-haloaryl ester products, exemplified by ethyl 2-(4-bromo-2-chlorophenyl)acetate (3a), can be further functionalized via palladium or copper catalysis to afford an array of a-aryl esters. (C) 2014 Elsevier Ltd. All rights reserved.