ethyl 3-bromo-2-oxooctanoate | 136496-64-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-bromo-2-oxooctanoate
• CAS: 136496-64-5
• 化学式: C₁₀H₁₇BrO₃
• 分子量: 265.147
• InChiKey: LQSMYGBGJLLJCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  ethyl 3-bromo-2-oxooctanoate 、 氨基甲酸甲酯 在 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以79%的产率得到5-pentyl-4-ethoxycarbonyl-4-oxazolin-2-one
  参考文献：
  名称：

  Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3-Bromo-2-ketoesters

  摘要：

  New methods for the synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters are described. Condensation of 3-nosyloxy-2-ketoesters with methyl carbamate in refluxing toluene in the presence of p-TSA provided 2-oxazolone-4-carboxylates in good yields (41-80%). Alternatively, bromination of alpha-ketoesters with CuBr2 provided 3-bromo-2-ketoesters which condensed with methyl carbamate in the presence of p-TSA and AgOTf under similar conditions to provide 2-oxazolone-4-carboxylates in comparable yields (30-79%). The 2-oxazolone-4-carboxylates bear functionality that can be elaborated to a variety of potentially useful compounds. For example, some of these heterocycles were readily N-acylated, reduced to alcohols, or saponified and coupled with amino acids.

  DOI：

  10.1021/jo010630z
• 作为产物：
  描述：

  2-氧代辛酸乙酯 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 18.0h， 以88%的产率得到ethyl 3-bromo-2-oxooctanoate
  参考文献：
  名称：

  Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3-Bromo-2-ketoesters

  摘要：

  New methods for the synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters are described. Condensation of 3-nosyloxy-2-ketoesters with methyl carbamate in refluxing toluene in the presence of p-TSA provided 2-oxazolone-4-carboxylates in good yields (41-80%). Alternatively, bromination of alpha-ketoesters with CuBr2 provided 3-bromo-2-ketoesters which condensed with methyl carbamate in the presence of p-TSA and AgOTf under similar conditions to provide 2-oxazolone-4-carboxylates in comparable yields (30-79%). The 2-oxazolone-4-carboxylates bear functionality that can be elaborated to a variety of potentially useful compounds. For example, some of these heterocycles were readily N-acylated, reduced to alcohols, or saponified and coupled with amino acids.

  DOI：

  10.1021/jo010630z

文献信息

• Catalytic, Asymmetric, “Interrupted” Feist−Bénary Reactions
  作者：Michael A. Calter、Ryan M. Phillips、Christine Flaschenriem

  DOI：10.1021/ja055752d

  日期：2005.10.1

  Pyrimidine derivatives of the cinchona alkaloids function as excellent asymmetric catalysts for the "Interrupted" Feist-Bénary Reaction. This reaction produces highly substituted hydroxydihydrofurans from simple starting materials under mild conditions. The asymmetric reaction gives high enantioselectivities with unsubstituted bromoketones, and high enantio- and diastereoselectivities with substituted substrates. Mechanistic experiments suggest that the hydrobromide salt of the alkaloid derivative is the active catalyst for the reaction.
• Shchepin, V.V.; Kotel'nikov, A.G.; Gladkova, G.E., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 2, p. 246 - 249
  作者：Shchepin, V.V.、Kotel'nikov, A.G.、Gladkova, G.E.

  DOI：——

  日期：——
• SHCHEPIN, V. V.;KOTELNIKOV, A. G.;GLADKOVA, G. E., ZH. ORGAN. XIMII, 27,(1991) N, S. 290-294
  作者：SHCHEPIN, V. V.、KOTELNIKOV, A. G.、GLADKOVA, G. E.

  DOI：——

  日期：——
• Synthesis of 2-Oxazolone-4-carboxylates from 3-Nosyloxy- and 3-Bromo-2-ketoesters
  作者：John F. Okonya、Robert V. Hoffman、M. Catherine Johnson

  DOI：10.1021/jo010630z

  日期：2002.2.1

  New methods for the synthesis of 2-oxazolone-4-carboxylates from 3-nosyloxy- and 3-bromo-2-ketoesters are described. Condensation of 3-nosyloxy-2-ketoesters with methyl carbamate in refluxing toluene in the presence of p-TSA provided 2-oxazolone-4-carboxylates in good yields (41-80%). Alternatively, bromination of alpha-ketoesters with CuBr2 provided 3-bromo-2-ketoesters which condensed with methyl carbamate in the presence of p-TSA and AgOTf under similar conditions to provide 2-oxazolone-4-carboxylates in comparable yields (30-79%). The 2-oxazolone-4-carboxylates bear functionality that can be elaborated to a variety of potentially useful compounds. For example, some of these heterocycles were readily N-acylated, reduced to alcohols, or saponified and coupled with amino acids.