4-(4-methoxybenzyloxy)butanoic acid methyl ester | 78132-73-7

• 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)butanoic acid methyl ester
• 英文别名: Methyl 4-[(4-methoxyphenyl)methoxy]butanoate
• CAS: 78132-73-7
• 化学式: C₁₃H₁₈O₄
• mdl: MFCD12410054
• 分子量: 238.284
• InChiKey: KLESLUSGNHSOGK-UHFFFAOYSA-N

物化性质

• 沸点：
  332.7±27.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-methoxybenzyloxy)butanoic acid methyl ester 在 水 、 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 乙腈 为溶剂， 以91%的产率得到γ-丁内酯
  参考文献：
  名称：

  三苯基碳鎓和三（P溴苯基）铵基离子（ω -苄氧基诱导lactonizations和ω- P -methoxybenzyloxy甲酯

  摘要：

  标题反应通过2型中间体的甲氧基甲氧基的直接亲核参与导致平滑生成五元和六元内酯。

  DOI：

  10.1016/0040-4039(81)80004-4
• 作为产物：
  描述：

  4-(((4-methoxybenzyl)oxy)methyl)-2,2-dimethyl-1,3-dioxolane 在 palladium on activated charcoal 盐酸 、 sodium periodate 、 氢气 、 三苯基膦 、 methyloxirane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 132.0h， 生成 4-(4-methoxybenzyloxy)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

文献信息

• HOYE T. R.; KURTH M. J.; LO V., TETRAHEDRON LETT., 1981, 22, NO 9, 815-818
  作者：HOYE T. R.、 KURTH M. J.、 LO V.

  DOI：——

  日期：——
• Synthesis of 13C-labeled γ-hydroxybutyrates for EPR studies with 4-hydroxybutyryl-CoA dehydratase
  作者：Ulrike Näser、Antonio J. Pierik、Richard Scott、Irfan Çinkaya、Wolfgang Buckel、Bernard T. Golding

  DOI：10.1016/j.bioorg.2004.09.001

  日期：2005.2

  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.
• Triphenylcarbenium and tris(P-bromophenyl)ammoniumyl ion induced lactonizations of (ω-benzyloxy and ω-P-methoxybenzyloxy methyl esters
  作者：Thomas R. Hoye、Mark J. Kurth、Vincent Lo

  DOI：10.1016/0040-4039(81)80004-4

  日期：1981.1

  The title reaction leads to smooth generation of five and six membered lactones via direct nucleophilic participation of the carbomethoxy group in intermediates of type .

  标题反应通过2型中间体的甲氧基甲氧基的直接亲核参与导致平滑生成五元和六元内酯。