methyl 2-(acetoxymethyl)-3-(2-bromophenyl)acrylate | 752254-58-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 2-(acetoxymethyl)-3-(2-bromophenyl)acrylate
• 英文别名: methyl (E)-2-(acetyloxymethyl)-3-(2-bromophenyl)prop-2-enoate
• CAS: 752254-58-3
• 化学式: C₁₃H₁₃BrO₄
• 分子量: 313.148
• InChiKey: MEXRWCCEDMDNJB-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl 2-(acetoxy(2-bromophenyl)methyl)acrylate 在 bismuth(lll) trifluoromethanesulfonate 作用下， 以 乙腈 为溶剂， 反应 35.0h， 以82%的产率得到methyl 2-(acetoxymethyl)-3-(2-bromophenyl)acrylate
  参考文献：
  名称：

  Bismuth triflate-catalyzed rearrangement of acetates of the Baylis–Hillman adducts into (E)-trisubstituted alkenes

  摘要：

  In the presence of a catalytic amount of bismuth triflate, methyl 3-acetoxy-3-aryl-2-methyl-enepropanoates and 3-acetoxy-3-aryl-2-methylenepropanitriles were smoothly converted into methyl (2E)-2-(acetoxymethyl)-3-arylprop-2-enoates and (2E)-2-(acetoxymethyl)-3-arylprop-2-enenitriles, respectively. A remarkable reversal in stereochemical directions from ester to nitrile was observed. 3-Aryl-3-hydroxy-2-methylenepropanoates and 3-aryl-3-hydroxy-2-methylenepropanitriles could be easily obtained as Baylis-Hillman adducts from methyl acrylate and acrylonitrile, respectively. The overall process is an efficient isomerization of the Baylis-Hillman adducts to the corresponding cinnamyl derivatives. The isomerization reaction proceeded rapidly and afforded smoothly the cinnamyl acetates in moderate to very good yields using catalytic amounts of Bi(OTf)(3)center dot 4H(2)O (10 mol%). (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.053