methyl 4-(2'-bromo-4'-fluorophenyl)-4-oxobutyrate | 579461-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-(2'-bromo-4'-fluorophenyl)-4-oxobutyrate
• 英文别名: Methyl 4-(2-bromo-4-fluorophenyl)-4-oxobutanoate；methyl 4-(2-bromo-4-fluorophenyl)-4-oxobutanoate
• CAS: 579461-39-5
• 化学式: C₁₁H₁₀BrFO₃
• 分子量: 289.101
• InChiKey: GBZVRBBZUSZKPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2'-bromo-4'-fluorophenyl)-4-oxobutyrate 在 barium dihydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到4-(2-bromo-4-fluorophenyl)-4-oxobutanoic acid
  参考文献：
  名称：

  Photoinduced cleavage of DNA by bromofluoroacetophenone–pyrrolecarboxamide conjugates

  摘要：

  Bromofluoroacetophenone derivatives which produce fluorine substituted phenyl radicals that cleave DNA upon excitation were investigated as a novel photonuclease. Pyrrolecarboxamide-conjugated bromofluoroacetophenones; 4'-bromo-2'-fluoroacetophenone and 2'-bromo-4'-fluoroacetophenone were synthesized and their DNA cleaving activities and sequence selectivities were determined. Bromofluoroacetophenone-pyrrolecarboxamide conjugates were. found to be effective DNA cleaving agents upon irradiation in concentration dependent manner based on plasma relaxation assay. The DNA cleaving activities of 2'-bromo-4'-fluoroacetophenone derivatives were larger than those of 4'-bromo-2'-fluoroacetophenone derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00212-9
• 作为产物：
  描述：

  间溴氟苯 、 丁二酸单甲酯酰氯 在 三氯化铝 作用下， 以 二硫化碳 为溶剂， 反应 4.0h， 生成 methyl 4-(4-bromo-2-fluorophenyl)-4-oxobutanoate 、 methyl 4-(2'-bromo-4'-fluorophenyl)-4-oxobutyrate
  参考文献：
  名称：

  Photoinduced cleavage of DNA by bromofluoroacetophenone–pyrrolecarboxamide conjugates

  摘要：

  Bromofluoroacetophenone derivatives which produce fluorine substituted phenyl radicals that cleave DNA upon excitation were investigated as a novel photonuclease. Pyrrolecarboxamide-conjugated bromofluoroacetophenones; 4'-bromo-2'-fluoroacetophenone and 2'-bromo-4'-fluoroacetophenone were synthesized and their DNA cleaving activities and sequence selectivities were determined. Bromofluoroacetophenone-pyrrolecarboxamide conjugates were. found to be effective DNA cleaving agents upon irradiation in concentration dependent manner based on plasma relaxation assay. The DNA cleaving activities of 2'-bromo-4'-fluoroacetophenone derivatives were larger than those of 4'-bromo-2'-fluoroacetophenone derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00212-9

文献信息

• Photoinduced cleavage of DNA by bromofluoroacetophenone–pyrrolecarboxamide conjugates
  作者：Paul A. Wender、Raok Jeon

  DOI：10.1016/s0960-894x(03)00212-9

  日期：2003.5

  Bromofluoroacetophenone derivatives which produce fluorine substituted phenyl radicals that cleave DNA upon excitation were investigated as a novel photonuclease. Pyrrolecarboxamide-conjugated bromofluoroacetophenones; 4'-bromo-2'-fluoroacetophenone and 2'-bromo-4'-fluoroacetophenone were synthesized and their DNA cleaving activities and sequence selectivities were determined. Bromofluoroacetophenone-pyrrolecarboxamide conjugates were. found to be effective DNA cleaving agents upon irradiation in concentration dependent manner based on plasma relaxation assay. The DNA cleaving activities of 2'-bromo-4'-fluoroacetophenone derivatives were larger than those of 4'-bromo-2'-fluoroacetophenone derivatives. (C) 2003 Elsevier Science Ltd. All rights reserved.