methyl 4-(4-bromophenyl)-4-(2,4-dimethoxyphenyl)-2-oxobutanoate | 1227202-79-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(4-bromophenyl)-4-(2,4-dimethoxyphenyl)-2-oxobutanoate
• CAS: 1227202-79-0
• 化学式: C₁₉H₁₉BrO₅
• 分子量: 407.261
• InChiKey: ABISBGLQXGQEJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4-(4-bromophenyl)-4-(2,4-dimethoxyphenyl)-2-oxobutanoate 、 methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 methyl 4-[5-(3-methoxycarbonyl-3-oxo-1-(4-bromophenyl)propyl)-2,4-dimethoxyphenyl]-2-oxo-4-(4-bromophenyl)butanoate 、 methyl 4-[5-(3-methoxycarbonyl-3-oxo-1-(4-bromophenyl)propyl)-2,4-dimethoxyphenyl]-2-oxo-4-(4-bromophenyl)butanoate
  参考文献：
  名称：

  Asymmetric Friedel–Crafts alkylation of activated benzenes with methyl (E)-2-oxo-4-aryl-3-butenoates catalyzed by [Pybox/Sc(OTf)3]

  摘要：

  The asymmetric Friedel-Crafts reaction between methyl (E)-2-oxo-4-aryl-3-butenoates (la-c) and activated benzenes (2a-d) has been efficiently catalyzed by the Sc-III triflate complex of (4'S,5'S)-2,6-bis[4'-(triisopropylsilyl) oxymethyl-5'-phenyl-1',3'-oxazolin-2'-yl]pyridine (pybox 3). The 4,4-diaryl-2-oxo-butyric acid methyl esters (4) are usually formed in good yields and the enantioselectivity is up to 99% ee. The sense of the stereoinduction can be rationalized with the same octahedral complex (10) between 1, pybox 3 and Sc triflate already proposed for other reactions involving pyruvates, and catalyzed by the same complex. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.054
• 作为产物：
  描述：

  methyl (E)-2-oxo-4-(4-bromophenyl)-3-butenoate 、 间苯二甲醚 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 12.25h， 以42%的产率得到methyl 4-(4-bromophenyl)-4-(2,4-dimethoxyphenyl)-2-oxobutanoate
  参考文献：
  名称：

  Asymmetric Friedel–Crafts alkylation of activated benzenes with methyl (E)-2-oxo-4-aryl-3-butenoates catalyzed by [Pybox/Sc(OTf)3]

  摘要：

  The asymmetric Friedel-Crafts reaction between methyl (E)-2-oxo-4-aryl-3-butenoates (la-c) and activated benzenes (2a-d) has been efficiently catalyzed by the Sc-III triflate complex of (4'S,5'S)-2,6-bis[4'-(triisopropylsilyl) oxymethyl-5'-phenyl-1',3'-oxazolin-2'-yl]pyridine (pybox 3). The 4,4-diaryl-2-oxo-butyric acid methyl esters (4) are usually formed in good yields and the enantioselectivity is up to 99% ee. The sense of the stereoinduction can be rationalized with the same octahedral complex (10) between 1, pybox 3 and Sc triflate already proposed for other reactions involving pyruvates, and catalyzed by the same complex. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.054