4-溴-3,3-二甲氧基-2-丁酮 | 547753-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-溴-3,3-二甲氧基-2-丁酮
• 英文名称: 4-bromo-3,3-dimethoxy-2-butanone
• 英文别名: 4-bromo-3,3-dimethoxybutan-2-one；4-Bromo-3,3-dimethoxybutan-2-one
• CAS: 547753-50-4
• 化学式: C₆H₁₁BrO₃
• 分子量: 211.056
• InChiKey: MBHBFMUEHAWTLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-溴-3,3-二甲氧基-2-丁酮 在 4-甲基苯磺酸吡啶 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以32%的产率得到(Z)-4-bromo-3-methoxybut-3-en-2-one
  参考文献：
  名称：

  （E）-4-溴-3-甲氧基但是-3-烯-2-酮的合成，多羟基链中的关键片段是链孢菌内酯和磷酰胺类A–C共有的

  摘要：

  首次合成了隐伏内酯和oscillariolides中存在的多羟基化链的末端溴甲氧基二烯（BMD）部分。描述了4-溴-3-甲氧基但是3-en-2-烯的立体选择合成的几种策略。此外，成功地将BMD引入多元醇链和脂肪酸的初步研究使我们能够证实多元醇的末端结构。

  DOI：

  10.1002/chem.201600770
• 作为产物：
  描述：

  甲醇 、 3,3-二甲氧基-2-丁酮 在 N,N-Diisopropylethylamine p-toluenesulfonate salt 、 N-溴代丁二酰亚胺(NBS) 作用下， 反应 3.0h， 以14.90 g的产率得到4-溴-3,3-二甲氧基-2-丁酮
  参考文献：
  名称：

  Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols

  摘要：

  Several 1-alkyl-2-methylazetidin-3-ones were prepared in good yield by the hydride-induced cyclization of the corresponding beta-bromo-alpha,alpha-dimethoxyketimines, the resulting 3,3-dimethoxyazetidines being hydrolyzed by acid. Imination of these 1,2-disubstituted azetidin-3-ones, followed by alkylation under kinetic control conditions resulted in regioisomeric mixtures of 2,4- and 2,2-dialkylated compounds. Analytical samples of the major 2,4-disubstituted derivatives were obtained after extensive chromatographic separation. The cis stereochemistry of the major 2,4-dialkylated isomer was demonstrated on the basis of NMR data. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00241-2

文献信息

• Synthesis of (<i>E</i>)-4-Bromo-3-methoxybut-3-en-2-one, the Key Fragment in the Polyhydroxylated Chain Common to Oscillariolide and Phormidolides A-C
  作者：Alejandro Gil、Janire Lamariano-Merketegi、Adriana Lorente、Fernando Albericio、Mercedes Álvarez

  DOI：10.1002/chem.201600770

  日期：2016.5.17

  The terminal bromomethoxydiene (BMD) moiety of the polyhydroxylated chain present in phormidolides and oscillariolides has been synthesized for first time. Several strategies for the stereoselective synthesis of the 4‐bromo‐3‐methoxybut‐3‐en‐2‐ones are described. Furthermore, a preliminary study to successfully introduce the BMD within the polyol chain and the fatty acid allowed us to corroborate the

  首次合成了隐伏内酯和oscillariolides中存在的多羟基化链的末端溴甲氧基二烯（BMD）部分。描述了4-溴-3-甲氧基但是3-en-2-烯的立体选择合成的几种策略。此外，成功地将BMD引入多元醇链和脂肪酸的初步研究使我们能够证实多元醇的末端结构。
• Synthesis of 1-alkyl-2-methylazetidin-3-ones and 1-alkyl-2-methylazetidin-3-ols
  作者：Antonio Salgado、Yves Dejaegher、Guido Verniest、Mark Boeykens、Christine Gauthier、Christelle Lopin、Kourosch Abbaspour Tehrani、Norbert De Kimpe

  DOI：10.1016/s0040-4020(03)00241-2

  日期：2003.3

  Several 1-alkyl-2-methylazetidin-3-ones were prepared in good yield by the hydride-induced cyclization of the corresponding beta-bromo-alpha,alpha-dimethoxyketimines, the resulting 3,3-dimethoxyazetidines being hydrolyzed by acid. Imination of these 1,2-disubstituted azetidin-3-ones, followed by alkylation under kinetic control conditions resulted in regioisomeric mixtures of 2,4- and 2,2-dialkylated compounds. Analytical samples of the major 2,4-disubstituted derivatives were obtained after extensive chromatographic separation. The cis stereochemistry of the major 2,4-dialkylated isomer was demonstrated on the basis of NMR data. (C) 2003 Elsevier Science Ltd. All rights reserved.