methyl 2-bromo-3-oxo-3-phenylpropanoate | 59864-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-bromo-3-oxo-3-phenylpropanoate
• 英文别名: alpha-Benzoyl-alpha-bromoacetic acid methyl ester
• CAS: 59864-01-6
• 化学式: C₁₀H₉BrO₃
• 分子量: 257.084
• InChiKey: LONSZFZHKVUSIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-3-oxo-3-phenylpropanoate 在 劳森试剂 、 copper(II) tetrafluroborate hexahydrate 、 三(2-吡啶基甲基)胺 、 二异丙胺 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 methyl 5-(4-methoxyphenyl)-2-phenyl-4,5-dihydrothiophene-3-carboxylate
  参考文献：
  名称：

  A Copper-Catalyzed Formal [3 + 2]-Cycloaddition for the Synthesis of All Different Aryl-Substituted Furans and Thiophenes

  摘要：

  A highly efficient formal [3 + 2]-cycloaddition was established using a copper catalyst. The resulting dihydrofurans were subjected to oxidation followed by arylations to produce tetraarylfurans. In addition, the dihydrofuran can be converted to diaryldihydrothiophene by using Lawesson's reagent. This protocol will facilitate the synthesis of all different aryl-substituted furans and thiophenes.

  DOI：

  10.1021/acs.joc.5b01139
• 作为产物：
  描述：

  苯甲酰乙酸甲酯 在 sodium methylate 、 溴 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以74%的产率得到methyl 2-bromo-3-oxo-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis of thiazolyl-based hydroxamic acids as histone deacetylase inhibitors

  摘要：

  DOI：

  10.24820/ark.5550190.p011.279

文献信息

• One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction
  作者：Ajeet Chandra、Keshaba Nanda Parida、Jarugu Narasimha Moorthy

  DOI：10.1016/j.tet.2017.08.019

  日期：2017.10

  α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX)

  通过将中间溴代醇催化氧化与原位生成的修饰IBX作为关键反应，已经开发出了简单的一锅法，用于从烯烃开始合成α-溴代酮和α-叠氮酮。改进的方法包括通过在室温下使烯烃与NBS在乙腈-水混合物（1：1）中反应，然后再用原位生成的3,4,5,6-四甲基-2-碘氧基苯甲酸（（TetMe-IBX），以催化量由3,4,5,6-四甲基-2-碘苯甲酸和Oxone制得。使用NaN 3 / NaHCO 3在同一个锅中将α-溴酮进一步转化为相应的α-叠氮酮。一锅转换对于包括环以及无环脂族烯烃以及富电子和缺电子的苯乙烯在内的多种烯烃是通用的。对于同时含有富电子和不足双键的底物，已证明了富电子双键的化学选择性溴羟基化和随后的氧化成α-溴代酮。
• One-pot synthesis of quinoxaline-2-carboxylate derivatives using ionic liquid as reusable reaction media
  作者：H.M. Meshram、P. Ramesh、G. Santosh Kumar、B. Chennakesava Reddy

  DOI：10.1016/j.tetlet.2010.05.099

  日期：2010.8

  The catalyst-free one-pot synthesis of quinoxaline-2-carboxylate is reported by the reaction of alpha-halo-beta-ketoesters with 1,2-diamines using an ionic liquid as an environmentally benign solvent The recovered ionic liquid was reused for four to five cycles Moreover, the method is applicable for a variety of 1,2-diamines and alpha-halo-beta-ketoesters (c) 2010 Elsevier Ltd All rights reserved
• Synthesis of thiazolyl-based hydroxamic acids as histone deacetylase inhibitors
  作者：Yodita Asfaha、Alexander Jan Skerhut、Leandro A. Alves-Avelar、Nadine Horstick-Muche、Beate Lungerich、Stefan Klinken、Matthias U. Kassack、Thomas Kurz

  DOI：10.24820/ark.5550190.p011.279

  日期：——
• A Copper-Catalyzed Formal [3 + 2]-Cycloaddition for the Synthesis of All Different Aryl-Substituted Furans and Thiophenes
  作者：Shingo Ishikawa、Yushi Noda、Masaru Wada、Takashi Nishikata

  DOI：10.1021/acs.joc.5b01139

  日期：2015.8.7

  A highly efficient formal [3 + 2]-cycloaddition was established using a copper catalyst. The resulting dihydrofurans were subjected to oxidation followed by arylations to produce tetraarylfurans. In addition, the dihydrofuran can be converted to diaryldihydrothiophene by using Lawesson's reagent. This protocol will facilitate the synthesis of all different aryl-substituted furans and thiophenes.