1-(3,4-二甲氧基苯基)-2-(2-甲氧基苯氧基)-1-丙酮 | 1835-09-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3,4-二甲氧基苯基)-2-(2-甲氧基苯氧基)-1-丙酮
• 英文名称: α-Guajacoxy-propioveratron
• 英文别名: 1-(3,4 Dimethoxyphenyl)-2-(-2-phenoxy-1-methoxy)-1-propanone；1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propan-1-one
• CAS: 1835-09-2
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: VSFLOUIGMNOHRL-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C
• 沸点：
  459.9±40.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,4-二甲氧基苯基)-2-(2-甲氧基苯氧基)-1-丙酮 在 sodium tetrahydroborate 作用下， 生成 苯甲醇,3,4-二甲氧基-a-[1-(2-甲氧基苯氧基)乙基]-
  参考文献：
  名称：

  Gieser,J.; Noren,I., Acta Chemica Scandinavica (1947), 1962, vol. 16, p. 1713 - 1729

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3,4-二甲氧基苯基)-1-丙酮 在 溴 、 potassium carbonate 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 0.33h， 生成 1-(3,4-二甲氧基苯基)-2-(2-甲氧基苯氧基)-1-丙酮
  参考文献：
  名称：

  Electroorganic reactions. 38. Mechanism of electrooxidative cleavage of lignin model dimers

  摘要：

  The mechanisms for oxidative cleavage of several phenolic ethers, models for lignins, have been investigated by a detailed comparison of the result of anodic oxidation at nickel anodes in alkaline electrolyte with that of oxidation in acetonitrile in the presence of a triarylamine redox catalyst. The latter reaction is unambiguously initiated by single-electron transfer (SET), and in this case the major product of cleavage is aldehyde (vanillin or syringaldehyde derivatives). At nickel anodes polymerization is predominant although the aldehydes are formed together with larger amounts of the corresponding carboxylic acids. Combinations of 4-hydroxyl, alpha-keto, beta-O-aryl, and beta-hydroxymethyl functionality are shown to be crucial for the oxidation at nickel; the carboxylic acid formation probably involves a route with initial hydrogen atom abstraction at the surface. Important chemical conversions precede and accompany oxidation in alkaline media, and these are associated with the propensity for polymerization.

  DOI：

  10.1021/jo00026a022

文献信息

• Rhodium-terpyridine catalyzed redox-neutral depolymerization of lignin in water
  作者：Yuxuan Liu、Changzhi Li、Wang Miao、Weijun Tang、Dong Xue、Jianliang Xiao、Tao Zhang、Chao Wang

  DOI：10.1039/c9gc03057c

  日期：——

  ketones and phenols, the catalytic system could also be applied to depolymerize dioxasolv lignin and lignocellulose, affording aromatic ketones as the major monomer products. The (hemi)cellulose components in the lignocellulose sample remain almost intact during lignin depolymerization, providing an example of a “lignin-first” process under mild conditions. Mechanistic studies suggest that the reaction

  发现简单的铑吡啶吡啶络合物是木质素在水中的氧化还原中性裂解的合适催化剂。除了将木质素模型化合物裂解为酮和酚外，该催化体系还可以用于解聚二氧杂酚木质素和木质纤维素，从而提供芳香族酮作为主要单体产物。木质纤维素样品中的（半）纤维素成分在木质素解聚过程中几乎保持完整，这是在温和条件下“木质素优先”过程的一个例子。机理研究表明，该反应通过铑催化的氢自转移过程进行。
• Ruthenium-Catalyzed CC Bond Cleavage in Lignin Model Substrates
  作者：Thorsten vom Stein、Tim den Hartog、Julien Buendia、Spas Stoychev、Jakob Mottweiler、Carsten Bolm、Jürgen Klankermayer、Walter Leitner

  DOI：10.1002/anie.201410620

  日期：2015.5.11

  Ruthenium–triphos complexes exhibited unprecedented catalytic activity and selectivity in the redox‐neutral CC bond cleavage of the β‐O‐4 lignin linkage of 1,3‐dilignol model compounds. A mechanistic pathway involving a dehydrogenation‐initiated retro‐aldol reaction for the CC bond cleavage was proposed in line with experimental data and DFT calculations.

  钌-三膦络合物氧化还原中性Ç表现出前所未有的催化活性和选择性的β-O-4木质素1,3- dilignol模型化合物键的C键断裂。根据实验数据和DFT计算，提出了一种涉及脱氢引发的逆式羟醛反应进行CC键断裂的机理。
• Maiorova, E. D.; Platonov, A. Yu.; Evstigneev, E. I., Journal of general chemistry of the USSR, 1992, vol. 62, # 5.2, p. 959 - 963
  作者：Maiorova, E. D.、Platonov, A. Yu.、Evstigneev, E. I.、Chistokletov, V. N.

  DOI：——

  日期：——
• DIMMEL, D. R.;SHEPARD, D., J. ORG. CHEM., 1982, 47, N 24, 4799-4800
  作者：DIMMEL, D. R.、SHEPARD, D.

  DOI：——

  日期：——
• GRABKINA, O. A.;BABKIN, V. A.;MEDVEDEVA, S. A.;IVANOVA, S. Z.;PAVLINSKIJ,+, XIMIYA DREVESINY,(1987) N 5, 34-40, 121, 122
  作者：GRABKINA, O. A.、BABKIN, V. A.、MEDVEDEVA, S. A.、IVANOVA, S. Z.、PAVLINSKIJ,+

  DOI：——

  日期：——