4-(4-methoxybenzyloxy)[1,2,3,4-13C4]but-2-enoic acid methyl ester | 848486-85-1

• 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: 4-(4-methoxybenzyloxy)[1,2,3,4-13C4]but-2-enoic acid methyl ester
• CAS: 848486-85-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 240.224
• InChiKey: ZQWJWTLVPYUZET-BBEXWYGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(4-methoxybenzyloxy)[1,2,3,4-13C4]but-2-enoic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 4-(4-methoxybenzyloxy)[1,2,3,4-13C4]butanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of 13C-labeled γ-hydroxybutyrates for EPR studies with 4-hydroxybutyryl-CoA dehydratase

  摘要：

  4-Hydroxybutyryl-CoA dehydratase from Clostridium aminobutyricum catalyses the reversible dehydration of its substrate 4-hydroxybutyryl-CoA (4-HB-CoA) to crotonyl CoA. The enzyme contains one [4Fe-4S](2+) cluster and one flavin adenine dinucleotide (FAD) molecule per homotetramer. Incubation of the enzyme with its substrate under equilibrium conditions followed by freezing at 77 K induced the EPR-spectrum of a neutral flavin semiquinone (g = 2.005, linewidth 2.1 mT), while at 10 K additional signals were detected. In an attempt to characterize these signals, 4-HB-CoA molecules specifically labeled with C-13 have been synthesized. This was achieved via C-13-labeled gamma-butyrolactones, which were obtained from C-13-labeled bromoacetic acids by efficient synthetic routes. Incubation of the C-13-labeled 4-hydroxybutyrate-CoA molecules with 4-hydroxybutyryi-CoA dehydratase did not lead to marked broadening of the signals.(C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.09.001
• 作为产物：
  描述：

  (4-methoxybenzyloxy)[1,2-13C]acetic acid methyl ester 在 lithium aluminium tetrahydride 、 戴斯-马丁氧化剂 、 三苯基膦 、 methyloxirane 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 4-(4-methoxybenzyloxy)[1,2,3,4-13C4]but-2-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis of 13C-labeled γ-hydroxybutyrates for EPR studies with 4-hydroxybutyryl-CoA dehydratase

  摘要：

  4-Hydroxybutyryl-CoA dehydratase from Clostridium aminobutyricum catalyses the reversible dehydration of its substrate 4-hydroxybutyryl-CoA (4-HB-CoA) to crotonyl CoA. The enzyme contains one [4Fe-4S](2+) cluster and one flavin adenine dinucleotide (FAD) molecule per homotetramer. Incubation of the enzyme with its substrate under equilibrium conditions followed by freezing at 77 K induced the EPR-spectrum of a neutral flavin semiquinone (g = 2.005, linewidth 2.1 mT), while at 10 K additional signals were detected. In an attempt to characterize these signals, 4-HB-CoA molecules specifically labeled with C-13 have been synthesized. This was achieved via C-13-labeled gamma-butyrolactones, which were obtained from C-13-labeled bromoacetic acids by efficient synthetic routes. Incubation of the C-13-labeled 4-hydroxybutyrate-CoA molecules with 4-hydroxybutyryi-CoA dehydratase did not lead to marked broadening of the signals.(C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2004.09.001