3-(O-Benzyl-guajacyl)-3-hydroxy-propionsaeure-aethylester | 94385-68-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(O-Benzyl-guajacyl)-3-hydroxy-propionsaeure-aethylester
• 英文别名: Ethyl 3-[4-(Benzyloxy)-3-methoxyphenyl]-3-hydroxypropanoate；ethyl 3-hydroxy-3-(3-methoxy-4-phenylmethoxyphenyl)propanoate
• CAS: 94385-68-9
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: YRIYIQOTBHHKRY-UHFFFAOYSA-N

物化性质

• 沸点：
  490.5±45.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(O-Benzyl-guajacyl)-3-hydroxy-propionsaeure-aethylester 在 一水合肼 作用下， 生成 3--3-hydroxy-propionsaeure-hydrazid
  参考文献：
  名称：

  Zur Synthese des 1-Guajacyl-propandiols-(1,3)

  摘要：

  DOI：

  10.1007/bf00903493
• 作为产物：
  描述：

  ethyl (4-benzyloxy-3-methoxybenzoyl)acetate 在 copper chromite 氢气 作用下， 以 乙醇 为溶剂， 生成 3-(O-Benzyl-guajacyl)-3-hydroxy-propionsaeure-aethylester
  参考文献：
  名称：

  Zur Synthese des 1-Guajacyl-propandiols-(1,3)

  摘要：

  DOI：

  10.1007/bf00903493

文献信息

• Synthesis of β-hydroxy esters using highly active manganese
  作者：YoungSung Suh、Reuben D. Rieke

  DOI：10.1016/j.tetlet.2003.11.045

  日期：2004.2

  A modified Reformatsky reaction is reported using highly reactive manganese (Mn*). The active manganese was found to readily react with α-haloester in the presence of aldehydes and ketones to yield the corresponding β-hydroxy esters. The reaction is carried out at room temperature in the absence of Lewis acid or trapping agents.

  据报道使用高反应性锰（Mn *）进行了改良的Reformatsky反应。发现该活性锰在醛和酮的存在下容易与α-卤代酯反应以产生相应的β-羟基酯。该反应在室温下在没有路易斯酸或捕集剂的条件下进行。
• Chemical synthesis of β-O-4 type artificial lignin
  作者：Takao Kishimoto、Yasumitsu Uraki、Makoto Ubukata

  DOI：10.1039/b518005h

  日期：——

  An artificial lignin polymer containing only the β-O-4 substructure was synthesized. The procedure consists of two key steps: 1) polycondensation of a brominated monomer by aromatic Williamson reaction; and 2) subsequent reduction of the carbonyl polymer. 13C-NMR and HMQC spectra of the polymer were consistent with β-O-4 substructures in milled wood lignin isolated from Japanese fir wood. The weight average degree of polymerization (DPw) ranged from 19.5 to 30.6, which is comparable to enzymatically synthesized artificial lignin from p-hydroxycinnamyl alcohols (dehydrogenation polymer, DHP) and some isolated lignins. Using this new lignin model polymer, it will now be possible to reinvestigate the properties and reactivity of the main lignin structure in terms of its polymeric character.

  合成了一种仅含有β-O-4亚结构的人工木质素聚合物。该过程包括两个关键步骤：1) 通过芳香威廉姆森反应对溴化单体进行聚缩合；2) 随后对羰基聚合物进行还原。聚合物的13C-NMR和HMQC谱与从日本冷杉木材中分离出的木材木质素中的β-O-4亚结构一致。聚合物的重量平均聚合度（DPw）范围为19.5至30.6，与从对羟基肉桂醇酶合成的人工木质素（脱氢聚合物，DHP）和一些分离的木质素相当。利用这种新的木质素模型聚合物，现在将有可能重新研究主要木质素结构在其聚合物特性方面的性质和反应性。
• Arylpropane-1,3-diols in Lignins from Normal and CAD-Deficient Pines
  作者：John Ralph、Hoon Kim、Junpeng Peng、Fachuang Lu

  DOI：10.1021/ol9906559

  日期：1999.7.1

  have been identified in lignins isolated from a CAD-deficient pine mutant; smaller amounts are also present in lignins from normal pine. They arise from dihydroconiferyl alcohol via the action of peroxidases which are responsible for the radical generation steps of lignification. The structures in the complex lignin polymers are proven using 2D and 3D NMR of isolated lignin fractions.

  在从缺乏CAD的松树突变体中分离出的木质素中，已经鉴定出大量的1,3-丙二醇。普通松木中的木质素含量也较少。它们由过氧化酶的作用由二氢松柏油基醇产生，过氧化物酶负责木质化的自由基生成步骤。使用分离的木质素级分的2D和3D NMR证明了复杂木质素聚合物中的结构。
• 3-Arylpropionylhydroxamic acid derivatives as Helicobacter pylori urease inhibitors: Synthesis, molecular docking and biological evaluation
  作者：Wei-Kang Shi、Rui-Cheng Deng、Peng-Fei Wang、Qin-Qin Yue、Qi Liu、Kun-Ling Ding、Mei-Hui Yang、Hong-Yu Zhang、Si-Hua Gong、Min Deng、Wen-Run Liu、Qiu-Ju Feng、Zhu-Ping Xiao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2016.07.052

  日期：2016.10

  Helicobacter pylori urease is involved in several physiologic responses such as stomach and duodenal ulcers, adenocarcinomas and stomach lymphomas. Thus, inhibition of urease is taken for a good chance to treat H. pylori-caused infections, we have therefore focused our efforts on seeking novel urease inhibitors. Here, a series of arylpropionylhydroxamic acids were synthesized and evaluated for urease inhibition. Out of these compounds, 3-(2-benzyloxy-5-chlorophenyl)-3-hydroxypropionylhydroxamic acid (d24) was the most active inhibitor with IC50 of 0.15 +/- 0.05 mu M, showing a mixed inhibition with both competitive and uncompetitive aspects. Non-linear fitting of kinetic data gives kinetics parameters of 0.13 and 0.12 mu g.mL(-1) for K-i and K-i', respectively. The plasma protein binding assays suggested that d24 exhibited moderate binding to human and rabbit plasma proteins. (C) 2016 Elsevier Ltd. All rights reserved.
• Ciofi-Baffoni, Simone; Banci, Lucia; Brandi, Alberto, Journal of the Chemical Society. Perkin transactions I, 1998, # 19, p. 3207 - 3217
  作者：Ciofi-Baffoni, Simone、Banci, Lucia、Brandi, Alberto

  DOI：——

  日期：——