2-bromo-3-(furan-2-yl)acrylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-bromo-3-(furan-2-yl)acrylic acid
• 英文别名: (Z)-2-bromo-3-(furan-2-yl)prop-2-enoic acid
• 化学式: C₇H₅BrO₃
• 分子量: 217.019
• InChiKey: OJIUMQCFSUQILV-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苄脒盐酸盐 、 2-bromo-3-(furan-2-yl)acrylic acid 在 copper(I) oxide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以67%的产率得到4-Furfurylidene-2-phenyl-2-imidazolin-5-one
  参考文献：
  名称：

  Simple and Efficient Copper-Catalyzed Approach to 2,4-Disubstituted Imidazolones

  摘要：

  Some imidazolone derivatives are biological and pharmaceutical active molecules and the chromophores of the fluorescent proteins. In this communication, a simple and efficient approach to 4-arylidene-2-alkyl-4,5-dihydro-1H-imidazol-5-ones (2,4-disubstituted imidazolones) has been developed, and the protocol uses readily available 2-bromo-3-alkylacrylic acids and amidines as the starting materials without addition of any ligand or additive. The reactions were performed under mild conditions. Therefore, the present method will be of wide application in organic chemistry and medicinal chemistry.

  DOI：

  10.1021/ol1008813
• 作为产物：
  描述：

  (Z)-ethyl 3-(furan-2-yl)-2-bromoprop-2-enoate 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以68%的产率得到2-bromo-3-(furan-2-yl)acrylic acid
  参考文献：
  名称：

  Simple and Efficient Copper-Catalyzed Approach to 2,4-Disubstituted Imidazolones

  摘要：

  Some imidazolone derivatives are biological and pharmaceutical active molecules and the chromophores of the fluorescent proteins. In this communication, a simple and efficient approach to 4-arylidene-2-alkyl-4,5-dihydro-1H-imidazol-5-ones (2,4-disubstituted imidazolones) has been developed, and the protocol uses readily available 2-bromo-3-alkylacrylic acids and amidines as the starting materials without addition of any ligand or additive. The reactions were performed under mild conditions. Therefore, the present method will be of wide application in organic chemistry and medicinal chemistry.

  DOI：

  10.1021/ol1008813

文献信息

• Palladium-Catalyzed Heteroannulation of 1,3-Dienes To Form α-Alkylidene-γ-butyrolactones
  作者：Steve V. Gagnier、Richard C. Larock

  DOI：10.1021/jo991692g

  日期：2000.3.1

  by the palladium-catalyzed heteroannulation of a variety of 1,3-dienes by alpha-iodo and alpha-bromo acrylic acids. The best results are obtained by employing a catalytic amount of the sterically hindered chelating alkyl phosphine D-t-BPF [(di-tert-butylphosphino)ferrocene]. In most cases, this process is highly regioselective. The reaction is believed to proceed via (1) oxidative addition of the vinylic

  α-亚炔基-γ-丁内酯很容易通过α-碘和α-溴丙烯酸的钯催化多种1,3-二烯的杂环化反应制得。通过使用催化量的空间受阻的螯合烷基膦Dt-BPF [（二叔丁基膦基）二茂铁]可获得最佳结果。在大多数情况下，该过程是高度区域选择性的。据信该反应是通过（1）将乙烯基卤化物氧化加成到Pd（0）上，（2）将有机钯加成到1,3-二烯的受阻较小的末端而形成pi-烯丙基钯中间体，和（3） ）通过羧酸根离子对钯的亲核取代