ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate
• 化学式: C₁₀H₁₇BrO₃
• 分子量: 265.147
• InChiKey: RUCQRODLNZMCSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 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：

  2-碘苯甲醛 、 ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate 在 锌 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 0.5h， 以70%的产率得到6-(2-Iodophenyl)-3,3,5,5-tetramethyldihydro-2H-pyran-2,4(3H)-dione
  参考文献：
  名称：

  摘要：

  Zinc enolates formed from ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate react under the conditions of one- of two-stage synthesis with aliphatic, unsaturated, or aromatic aldehydes to form 6-R-2,2,4,4-tetramethyl-2,3,5,6-tetrahydropyran-2,4-diones. Zinc enolates obtained from ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate, -hexanoate, and -2,2,5-trimethyl-3-oxohexanoate under the similar conditions react with aliphatic or aromatic aldehydes to give mainly 5-R-1-6-R-2-3,3-dimethyl-2,3,5,6-tetrahydropyran-2,4-diones as E or Z isomers or their mixtures. Zinc enolates generated from the ethyl 4-bromo-2,2-diethyl- or 2-benzyl-2-ethyl-3-oxobutanoates react with aromatic aldehydes to give ethyl 5-R-2-R-2-ethyl-3-oxo-4-pentenoates as E isomers.

  DOI：

  10.1023/a:1025600905960

文献信息

• Synthesis of 6-hetaryl-5,5-dialkyl-3,3-dimethyl-tetrahydropyran-2,4-diones by Reformatsky Reaction
  作者：V. V. Shchepin、A. E. Korzun、Yu. Kh. Sazhneva

  DOI：10.1007/s11178-005-0049-6

  日期：2004.10

  Zinc enolates derived from ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate and 4-bromo-4- ethyl-2,2-dimethyl-3-oxohexanoate react with 2-furan-, 2-thiophene-, 1-(3-nitrophenyl)-2-pyrrole-, 1-acyl-3-indole-, and 2-pyridinecarbaldehydes to give the corresponding 6-hetaryl-5,5-dialkyl-3,3-dimethyltetrahydropyran-2,4-diones.

  由乙基4-溴-2,2,4-三甲基-3-氧代戊酸酯和4-溴-4-乙基-2,2-二甲基-3-氧代己酸酯衍生的锌烯醇盐与2-呋喃、2-噻吩、1-(3-硝基苯基)-2-吡咯、1-酰基-3-吲哚和2-吡啶甲醛反应，生成相应的6-杂芳基-5,5-二烷基-3,3-二甲基四氢吡喃-2,4-二酮。
• ——
  作者：V. V. Shchepin、A. E. Korzun、Yu. Kh. Sazhneva、A. N. Nedugov

  DOI：10.1023/a:1017531821831

  日期：——
• Shchepin, V. V.; Gladkova, G. E., Russian Journal of Organic Chemistry, 1995, vol. 31, # 7, p. 1016
  作者：Shchepin, V. V.、Gladkova, G. E.

  DOI：——

  日期：——
• Shchepin, V. V.; Gladkova, G. E.; Gess, I. B., Russian Journal of Organic Chemistry, 1993, vol. 29, # 3.1, p. 408 - 412
  作者：Shchepin, V. V.、Gladkova, G. E.、Gess, I. B.

  DOI：——

  日期：——
• ——
  作者：V. V. Shchepin、Yu. Kh. Sazhneva、D. N. Litvinov

  DOI：10.1023/a:1025600905960

  日期：——

  Zinc enolates formed from ethyl 4-bromo-2,2,4-trimethyl-3-oxopentanoate react under the conditions of one- of two-stage synthesis with aliphatic, unsaturated, or aromatic aldehydes to form 6-R-2,2,4,4-tetramethyl-2,3,5,6-tetrahydropyran-2,4-diones. Zinc enolates obtained from ethyl 4-bromo-2,2-dimethyl-3-oxopentanoate, -hexanoate, and -2,2,5-trimethyl-3-oxohexanoate under the similar conditions react with aliphatic or aromatic aldehydes to give mainly 5-R-1-6-R-2-3,3-dimethyl-2,3,5,6-tetrahydropyran-2,4-diones as E or Z isomers or their mixtures. Zinc enolates generated from the ethyl 4-bromo-2,2-diethyl- or 2-benzyl-2-ethyl-3-oxobutanoates react with aromatic aldehydes to give ethyl 5-R-2-R-2-ethyl-3-oxo-4-pentenoates as E isomers.