tert-butyl 2-(4-bromophenyl)propionate | 138622-99-8

• 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: tert-butyl 2-(4-bromophenyl)propionate
• 英文别名: tert-butyl 2-(4-bromophenyl)propanoate
• CAS: 138622-99-8
• 化学式: C₁₃H₁₇BrO₂
• 分子量: 285.181
• InChiKey: CUKFUOMBQOQEJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  tert-butyl 2-(4-bromophenyl)propionate 在 1,2,3,4,5-五苯基-1′-(二叔丁基膦)二茂铁 、 三氟乙酸 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 45.0h， 生成 布洛芬
  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
• 作为产物：
  描述：

  2-溴丙酸叔丁酯 在 三甲基氯硅烷 、 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 1.25h， 生成 tert-butyl 2-(4-bromophenyl)propionate
  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

• Catalytic α-Hydroarylation of Acrylates and Acrylamides via an Interrupted Hydrodehalogenation Reaction
  作者：Alena M. Vasquez、John A. Gurak、Candice L. Joe、Emily C. Cherney、Keary M. Engle

  DOI：10.1021/jacs.0c03040

  日期：2020.6.10

  The palladium-catalyzed, α-selective hydroarylation of acrylates and acrylamides is reported. Under optimized conditions, this method is highly tolerant of a wide range of substrates including those with base sensitive functional groups and/or multiple enolizable carbonyl groups. A detailed mechanistic study was undertaken, and the high selectivity of this transformation was shown to be enabled by

  报道了钯催化的丙烯酸酯和丙烯酰胺的 α 选择性加氢芳基化。在优化条件下，该方法对多种底物具有高度耐受性，包括具有碱敏感官能团和/或多个可烯醇化羰基的底物。进行了详细的机理研究，表明这种转化的高选择性是通过形成 [PdII(Ar)(H)] 中间体实现的，该中间体将氢化物选择性插入 α 的 β 位， β-不饱和羰基化合物。
• Prasad, Chalasani S N; Adapa, Srinivas R, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 11, p. 1067 - 1068
  作者：Prasad, Chalasani S N、Adapa, Srinivas R

  DOI：——

  日期：——