3,5-dibromo-4-oxo-valeric acid methyl ester | 140663-07-6

• 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: 3,5-dibromo-4-oxo-valeric acid methyl ester
• 英文别名: 3,5-Dibrom-4-oxo-valeriansaeure-methylester；3,5-Dibromolevulinic acid methyl ester；methyl 3,5-dibromo-4-oxopentanoate
• CAS: 140663-07-6
• 化学式: C₆H₈Br₂O₃
• 分子量: 287.936
• InChiKey: GHDRNKQSJBQRAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  3,5-dibromo-4-oxo-valeric acid methyl ester 在 镍 盐酸 、 盐酸羟胺 、 氢气 、 sodium carbonate 、 三乙胺 、 对苯二酚 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 183.5h， 生成 Methyl 4,7-Dioxooctanoate
  参考文献：
  名称：

  Zimmer, Reinhold; Collas, Markus; Roth, Michael, Liebigs Annalen der Chemie, 1992, # 7, p. 709 - 714

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰丙酸甲酯 在 溴 作用下， 以 乙醚 为溶剂， 以99%的产率得到3,5-dibromo-4-oxo-valeric acid methyl ester
  参考文献：
  名称：

  Zimmer, Reinhold; Collas, Markus; Roth, Michael, Liebigs Annalen der Chemie, 1992, # 7, p. 709 - 714

  摘要：

  DOI：

文献信息

• Variation in the regioselectivity of levulinic acid bromination in ionic liquids
  作者：Alexander G. Zavozin、Natalya E. Kravchenko、Nikolay V. Ignat’ev、Sergei G. Zlotin

  DOI：10.1016/j.tetlet.2009.11.097

  日期：2010.1

  The reaction of levulinic acid and its esters with bromine in ionic liquids results in the formation of 3-bromo derivatives as the major products and not the 5-bromo substituted isomers, which are typically formed in organic solvents. The bromination of levulinic acid in ionic liquids in the presence of urea leads to the formation of 5-bromolevulinic acid.

  乙酰丙酸及其酯与溴在离子液体中的反应导致形成3-溴衍生物作为主要产物，而不是5-溴取代的异构体，后者通常在有机溶剂中形成。在尿素存在下离子液体中乙酰丙酸的溴化导致5-溴乙酰丙酸的形成。
• Reinvestigation of the sulfuric acid-catalysed cyclisation of brominated 2-alkyllevulinic acids to 3-alkyl-5-methylene-2(5H)-furanones
  作者：Anthony J. Manny、Staffan Kjelleberg、Naresh Kumar、Rocky de Nys、Roger W. Read、Peter Steinberg

  DOI：10.1016/s0040-4020(97)10034-5

  日期：1997.11

  through bromination and acid promoted lactonisation is described. The underlying reactions have been investigated using levulinic acid as a model, and the effects of varying the bromination conditions and changing acid concentration on product distribution are discussed. Dibromination proceeds best in CHCl3 and proceeds in EtOH-free CHCl3 without the complication of ester formation. Cyclisation occurs

  描述了由烷基取代的乙酰丙酸衍生物通过溴化和酸促进的内酯化合成乙基，丁基，己基和十二烷基取代的溴化物。使用乙酰丙酸作为模型，研究了潜在的反应，并讨论了改变溴化条件和改变酸浓度对产物分布的影响。二溴化在CHCl 3中进行得最好，在无EtOH的CHCl 3中进行，而不会形成酯。在98–100％H 2 SO 4中伴随氧化发生环化反应，但在100％H 2 SO 4中产生环戊内酯的产率最高。还描述了相关的贝克雷利物质的形成。
• Method for obtaining 5-halogenolaevulinic acid alkyl esters
  申请人：Aldenkortt Dr Sven

  公开号：US20050070727A1

  公开（公告）日：2005-03-31

  A method for obtaining a 5-bromolevulinic acid methyl ester or a 5-chlorolevulinic acid methyl ester from either a bromination mixture or a chlorination mixture, containing either a 5-bromo-levulinic acid methyl ester or a 5-chlorolevulinic acid methyl ester, respectively, produced by either brominating or chlorinating levulinic acid or a levulinic acid methyl ester, and further including the steps of dissolving the bromination or chlorination mixture in an organic solvent or solvent mixture and cooling the solution, preferably to −20° C.-−40° C., with the 5-bromolevulinic acid methyl ester or 5-chlorolaevulinic acid methyl ester being crystallized out of the solution. The 5-bromolevulinic acid methyl ester or 5-chlorolevulinic acid is then isolated by draining off the solution with the remaining bromination mixture or chlorination mixture, as appropriate.

  从溴化混合物或氯化混合物中获取5-溴丙酮酸甲酯或5-氯丙酮酸甲酯的方法，分别包含5-溴丙酮酸甲酯或5-氯丙酮酸甲酯，这些物质是通过溴化或氯化丙酮酸或丙酮酸甲酯产生的。进一步包括将溴化或氯化混合物溶解在有机溶剂或溶剂混合物中，并冷却溶液，最好冷却至-20°C至-40°C，其中5-溴丙酮酸甲酯或5-氯丙酮酸甲酯从溶液中结晶出来。然后通过排出剩余的溴化混合物或氯化混合物，分离出5-溴丙酮酸甲酯或5-氯丙酮酸甲酯。
• CONJUGATES OF 1,4,7-TRIAZA-CYCLONONANES, DINUCLEAR METAL COMPLEXES OF SUCH CONJUGATES, AND METHODS OF USE FOR BOTH 1,4,7-TRIAZA-CYCLONONANES AND CONJUGATES
  申请人：Bio-Rad Laboratories, Inc.

  公开号：EP2547666A1

  公开（公告）日：2013-01-23
• CONJUGATES OF 1,4,7-TRIAZACYCLONONANES, DINUCLEAR METAL COMPLEXES OF SUCH CONJUGATES, AND METHODS OF USE FOR BOTH 1,4,7-TRIAZACYCLONONANES AND CONJUGATES
  申请人：Berkelman Thomas R.

  公开号：US20120058565A1

  公开（公告）日：2012-03-08

  Conjugates of 1,3-bis(1,4,7-triazacyclonon-1-yl)-2-hydroxypropanes with a variety of conjugating members are used in the formation of dinuclear metal complexes which bind to phosphate esters. By virtue of their conjugated forms, the complexes are incorporated into chromatographic media, affinity binding reagents, and dyes, which make the complexes useful in a wide range of assays, separations, and purifications. In addition, dinuclear metal complexes of 1,3-bis(1,4,7-triazacyclonon-1-yl)-2-hydroxypropanes that are not so conjugated are used in the detection of phosphate esters of biological species by either MALDI-TOF mass spectrometry or by dye displacement.