3-乙酰氧基-2-(2-甲氧基苯氧基)-1-(3,4-二甲氧基苯基)-1-丙酮 | 32565-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙酰氧基-2-(2-甲氧基苯氧基)-1-(3,4-二甲氧基苯基)-1-丙酮
• 英文名称: 3-acetoxy-2-(2-methoxyphenoxy)-1-(3,4-dimethoxyphenyl)-1-propanone
• 英文别名: 3-acetoxy-1-(3,4-dimethoxy-phenyl)-2-(2-methoxy-phenoxy)-propan-1-one；3-Acetoxy-1-(3,4-dimethoxy-phenyl)-2-(2-methoxy-phenoxy)-propan-1-on；Veratrone acetate；[3-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-3-oxopropyl] acetate
• CAS: 32565-77-8
• 化学式: C₂₀H₂₂O₇
• 分子量: 374.39
• InChiKey: ODPYOMZIVHDXSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-乙酰氧基-2-(2-甲氧基苯氧基)-1-(3,4-二甲氧基苯基)-1-丙酮 在 氢氟酸 、 四甲基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.5h， 生成 3-(3,4-Dimethoxy-phenyl)-4,4,4-trifluoro-2-(2-methoxy-phenoxy)-butane-1,3-diol
  参考文献：
  名称：

  ¹⁹F Nuclear Magnetic Resonance Spectroscopy for the Elucidation of Carbonyl Groups in Lignins. 1. Model Compounds

  摘要：

  A new method for the detection of different classes of carbonyl groups in a series of carbonyl-containing lignin-like model compounds has been developed. The method is based on the selective fluoride-induced trifluoromethylation of carbonyl groups with (trifluoromethyl)trimethylsilane (TMS-CF3) in the presence of tetramethylammonium fluoride (TMAF), followed by hydrolysis with aqueous HF or TMAF in the case of quinones. In this study a series of ketones, aldehydes, quinones, and dimeric-lignin model compounds were quantitatively trifluoromethylated followed by F-19 NMR spectral analyses of the resulting fluorine-containing derivatives, allowing for a thorough understanding of their structure/F-19 chemical shift relationships. These studies have shown that the F-19-NMR chemical shifts of the trifluoromethyl groups vary significantly and consistently for various classes of carbonyl groups which may be present in complex lignocellulosic materials. These studies are to form the basis for the development of a novel and sensitive method that can be used to obtain quantitative information on the various carbonyl groups present in such materials.

  DOI：

  10.1021/jf960154r
• 作为产物：
  描述：

  3,4-二甲氧基苯乙酮 在 盐酸 、 sodium tetrahydroborate 、 pyridinium hydrobromide perbromide 、 氧气 、 硝酸 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 60.58h， 生成 3-乙酰氧基-2-(2-甲氧基苯氧基)-1-(3,4-二甲氧基苯基)-1-丙酮
  参考文献：
  名称：

  α，γ-二醇保护的木质素的高度选择性氧化和解聚

  摘要：

  木质素氧化为氧化的芳香分子提供了潜在的可持续途径。但是，目前使用真正的木质素的方法往往具有较低的选择性，且收率受到其提取过程中木质素降解的限制。我们开发了化学计量和催化氧化方法，使用2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）作为氧化剂/催化剂，以选择性地将乙缩醛脱保护并将α-OH氧化为酮。然后，使用甲酸/甲酸钠系统将氧化的木质素解聚，生成芳香族单体，其收率为36 mol％（在化学计量氧化的情况下）和31 mol％（在催化氧化的情况下）（基于原始的Klason）木质素）。对单一产物的选择性达到80％（丁香基丙烷二酮，对愈创木基丙烷二酮的选择性为10-13％）。

  DOI：

  10.1002/anie.201811630

文献信息

• Hydrogenolysis of a γ-Acetylated Lignin Model Compound with a Ruthenium–Xantphos Catalyst
  作者：Adam Wu、Jean Michel Lauzon、Brian R. James

  DOI：10.1007/s10562-014-1401-7

  日期：2015.2

  Catalytic hydrogenolysis of a gamma-acetylated dimer lignin model compound is effected using a Ru-xantphos catalyst. Mechanistic investigations show mono-aryl degradation products are generated from the beta-O-4 substrate as well as a terminal alkene ketone dimer (bis-aryl) that further dimerizes to a tetra-aryl product. Preliminary results using an acetylated kraft lignin as a substrate are also discussed.
• Highly Selective Oxidation and Depolymerization of α,γ‐Diol‐Protected Lignin
  作者：Wu Lan、Jean Behaghel de Bueren、Jeremy S. Luterbacher

  DOI：10.1002/anie.201811630

  日期：2019.2.25

  Lignin oxidation offers a potential sustainable pathway to oxygenated aromatic molecules. However, current methods that use real lignin tend to have low selectivity and a yield that is limited by lignin degradation during its extraction. We developed stoichiometric and catalytic oxidation methods using 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) as oxidant/catalyst to selectively deprotect the

  木质素氧化为氧化的芳香分子提供了潜在的可持续途径。但是，目前使用真正的木质素的方法往往具有较低的选择性，且收率受到其提取过程中木质素降解的限制。我们开发了化学计量和催化氧化方法，使用2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）作为氧化剂/催化剂，以选择性地将乙缩醛脱保护并将α-OH氧化为酮。然后，使用甲酸/甲酸钠系统将氧化的木质素解聚，生成芳香族单体，其收率为36 mol％（在化学计量氧化的情况下）和31 mol％（在催化氧化的情况下）（基于原始的Klason）木质素）。对单一产物的选择性达到80％（丁香基丙烷二酮，对愈创木基丙烷二酮的选择性为10-13％）。
• ¹⁹F Nuclear Magnetic Resonance Spectroscopy for the Elucidation of Carbonyl Groups in Lignins. 1. Model Compounds
  作者：Behzad C. Ahvazi、Dimitris S. Argyropoulos

  DOI：10.1021/jf960154r

  日期：1996.1.1

  A new method for the detection of different classes of carbonyl groups in a series of carbonyl-containing lignin-like model compounds has been developed. The method is based on the selective fluoride-induced trifluoromethylation of carbonyl groups with (trifluoromethyl)trimethylsilane (TMS-CF3) in the presence of tetramethylammonium fluoride (TMAF), followed by hydrolysis with aqueous HF or TMAF in the case of quinones. In this study a series of ketones, aldehydes, quinones, and dimeric-lignin model compounds were quantitatively trifluoromethylated followed by F-19 NMR spectral analyses of the resulting fluorine-containing derivatives, allowing for a thorough understanding of their structure/F-19 chemical shift relationships. These studies have shown that the F-19-NMR chemical shifts of the trifluoromethyl groups vary significantly and consistently for various classes of carbonyl groups which may be present in complex lignocellulosic materials. These studies are to form the basis for the development of a novel and sensitive method that can be used to obtain quantitative information on the various carbonyl groups present in such materials.

表征谱图