4-(4-methoxybenzyloxy)but-2-enoic acid methyl ester | 848486-68-0

• 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: 4-(4-methoxybenzyloxy)but-2-enoic acid methyl ester
• 英文别名: methyl 4-[(4-methoxyphenyl)methoxy]but-2-enoate
• CAS: 848486-68-0
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: ZQWJWTLVPYUZET-UHFFFAOYSA-N

物化性质

• 沸点：
  343.8±32.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

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)but-2-enoic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 30.0h， 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
• 作为产物：
  描述：

  2-(4-甲氧基苄氧基)乙醇 在 戴斯-马丁氧化剂 、 三苯基膦 、 methyloxirane 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 4-(4-methoxybenzyloxy)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

文献信息

• Synthesis of Fmoc-Protected Amino Alcohols via the Sharpless Asymmetric Aminohydroxylation Reaction Using FmocNHCl as the Nitrogen Source
  作者：Ryan Moreira、Matthew Diamandas、Scott D. Taylor

  DOI：10.1021/acs.joc.9b02491

  日期：2019.12.6

  The aminohydroxylation of various alkenes using FmocNHCl as a nitrogen source is reported. In general, in the absence of a ligand, the reaction provided racemic Fmoc-protected amino alcohols with excellent regioselectivity but in low to moderate yields. However, in some instances, the yield of an amino alcohol product and the regioselectivity could be altered by the addition of a catalytic amount of

  报道了使用FmocNHCl作为氮源的各种烯烃的氨基羟基化。通常，在不存在配体的情况下，该反应提供了外消旋的Fmoc保护的氨基醇，具有优异的区域选择性，但产率低至中等。但是，在某些情况下，可以通过添加催化量的三乙胺（TEA）来改变氨基醇产物的产率和区域选择性。使用（DHQD）2 PHAL（DHQD）或（DHQ）2进行此反应的Sharpless不对称变体（Sharpless不对称氨基羟基化（SAAH））与没有手性配体的相同反应相比，作为手性配体的PHAL（DHQ）更容易进行且收率更高。除两个实施例外，所有实施例的对映体比率（er）均超过90:10，许多实施例的er值均达到95：5或更高，这使得FmocNHCl成为制备手性氨基醇的高度实用的试剂。采用使用FmocNHCl的SAAH反应用于制备d -苏-β-hydroxyasparagine和d -苏-β-methoxyaspartate，对于Fmoc固相肽合成适当保护的。