ethyl 2-(4-bromo-2-methylphenyl)acetate | 1261456-10-3

• 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: ethyl 2-(4-bromo-2-methylphenyl)acetate
• 英文别名: Ethyl 2-(4-bromo-2-methylphenyl)acetate
• CAS: 1261456-10-3
• 化学式: C₁₁H₁₃BrO₂
• 分子量: 257.127
• InChiKey: BKGAMLGQFCBYBA-UHFFFAOYSA-N

物化性质

• 沸点：
  306.5±27.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-bromo-2-methylphenyl)acetate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 sodium hydride 、 联硼酸频那醇酯 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.5h， 生成 ethyl 1-[4-[6-[5-[(6-isopropoxypyrazin-2-yl)amino]-1-methyl-pyrazol-4-yl]-3-pyridyl]-2-methyl-phenyl]cyclopropanecarboxylate
  参考文献：
  名称：

  [EN] LYSOPHOSPHATIDIC ACID RECEPTOR 1 (LPAR1) INHIBITOR COMPOUNDS
  [FR] COMPOSÉS INHIBITEURS DU RÉCEPTEUR 1 DE L'ACIDE LYSOPHOSPHATIDIQUE (LPAR1)

  摘要：

  化合物的结构式（I）或其药用盐，使用方法和制备方法的描述。

  公开号：

  WO2019041340A1
• 作为产物：
  描述：

  5-溴-2-碘甲苯 、 bromozinc(1+),ethyl acetate 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 4.0h， 以58%的产率得到ethyl 2-(4-bromo-2-methylphenyl)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

• Aromatic Claisen Rearrangements of Benzyl Ketene Acetals: Conversion of Benzylic Alcohols to ( <i>ortho</i> ‐Tolyl)acetates
  作者：Jed M. Burns、Elizabeth H. Krenske、Ross P. McGeary

  DOI：10.1002/ejoc.201601354

  日期：2017.1.10

  Claisen rearrangements of benzyl vinyl ethers are much less facile than those of aliphatic allyl vinyl ethers, and their synthetic utility has remained relatively unexplored. A one-pot procedure is reported for the generation and Claisen rearrangement of benzyl vinyl ethers that contain an activating α-alkoxy substituent on the vinyl group. A [3,3]-sigmatropic mechanism was supported by trapping of the

  苄基乙烯基醚的克莱森重排远不如脂肪族烯丙基乙烯基醚的克莱森重排容易，并且它们的合成效用仍然相对未开发。据报道，一锅法用于生成和克莱森重排苄基乙烯基醚，在乙烯基上含有活化的 α-烷氧基取代基。通过在分子内 Alder-ene 反应中捕获中间体异甲苯来支持 [3,3]-σ 机制。
• Lysophosphatidic acid receptor 1 (LPAR1) inhibitor compounds
  申请人：Eli Lilly and Company

  公开号：US11365185B2

  公开（公告）日：2022-06-21

  The present invention provides a compound of formula (I) or a pharmaceutical salt thereof, use, methods for its preparation are described.

  本发明提供式(I)的化合物或其药学上可接受的盐、用途及其制备方法。
• LYSOPHOSPHATIDIC ACID RECEPTOR 1 (LPAR1) INHIBITOR COMPOUNDS
  申请人：Eli Lilly and Company

  公开号：EP3679032A1

  公开（公告）日：2020-07-15
• 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.
• [EN] LYSOPHOSPHATIDIC ACID RECEPTOR 1 (LPAR1) INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DU RÉCEPTEUR 1 DE L'ACIDE LYSOPHOSPHATIDIQUE (LPAR1)
  申请人：LILLY CO ELI

  公开号：WO2019041340A1

  公开（公告）日：2019-03-07

  A compound of formula (I) or a pharmaceutical salt thereof, use, methods for its preparation are described.

  化合物的结构式（I）或其药用盐，使用方法和制备方法的描述。