1-(3,5-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one | 38790-00-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,5-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
• 英文别名: 1-(3,5-Dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
• CAS: 38790-00-0
• 化学式: C₁₈H₂₀O₆
• 分子量: 332.353
• InChiKey: PDSBBAGMJIJFRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  1-(3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 新铜试剂 、 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以12%的产率得到1-(3,5-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one
  参考文献：
  名称：

  β-O-4木质素模型化合物选择性CC键裂解的铜催化剂

  摘要：

  AbstractThe reactivity of homogeneous copper catalysts towards the selective CC bond cleavage of both phenolic and non‐phenolic arylglycerol β‐aryl ether lignin model compounds has been explored. Several copper precursors, nitrogen ligands, and solvents were evaluated in order to optimize the catalyst system. Using the optimized catalyst system, copper(I) trifluoromethanesulfonate [Cu(OTf)]/L/TEMPO (L=2,6‐lutidine, TEMPO=2,2,6,6‐tetramethyl‐piperidin‐1‐yl‐oxyl), aerobic oxidation of the non‐phenolic β‐O‐4 lignin model compound proceeded with good selectivity for CαCβ bond cleavage, affording 3,5‐dimethoxybenzaldehyde as the major product. Aerobic oxidation of the corresponding phenolic β‐O‐4 lignin model proceeded with different selectivity, affording 2,6‐dimethoxybenzoquinone and α,β‐unsaturated aldehyde products resulting from cleavage of the CαCaryl bond. At low catalyst concentrations, however, a change in selectivity was observed as oxidation of the benzylic secondary alcohol predominated with both substrates.magnified image

  DOI：

  10.1002/adsc.201400463

文献信息

• Aerobic Oxidation of β-1 Lignin Model Compounds with Copper and Oxovanadium Catalysts
  作者：Baburam Sedai、Christian Díaz-Urrutia、R. Tom Baker、Ruilian Wu、L. A. “Pete” Silks、Susan K. Hanson

  DOI：10.1021/cs400636k

  日期：2013.12.6

  TEMPO = 2,2,6,6-tetramethyl-piperidin-1-yl-oxyl) in toluene for the same reaction afforded 3,5-dimethoxybenzaldehyde (5) and 4-methoxybenzaldehyde (6) as major products resulting from Cα–Cβ bond cleavage. Reactions of the corresponding phenolic lignin model compounds (2T, 2E) with 10 mol % CuOTf/2,6-lutidine/TEMPO gave ketone (9) as the major product, whereas 10 mol % (HQ)2VV(O)(OiPr) or a stoichiometric

  研究了均相的氧钒和铜催化剂对酚类和非酚类β-1木质素模型化合物的需氧氧化的反应性。使用六配位钒配合物（HQ）2 V V（O）（O i Pr）（HQ = 8-oxyquinolinate）作为吡啶的前催化剂，对非对映非酚β-1木质素模型（1T，1E）进行有氧氧化仲醇氧化制得的酮（3）和脱水酮（4）。相反，在甲苯中使用CuOTf / 2,6-lutidine / TEMPO（OTf =三氟甲磺酸盐，TEMPO = 2,2,6,6-四甲基哌啶-1-基氧基）进行相同反应，得到3,5-二甲氧基苯甲醛（5）和4-甲氧基苯甲醛（6），其选自C所得产品主要α -C β键裂解。相应的酚类木质素模型化合物（2T，2E）与10 mol％CuOTf / 2,6-lutidine / TEMPO的反应生成酮（9）作为主要产物，而10 mol％（HQ）2 V V（O）（ ø我PR）或CuOTf的化学计量的量/ 2,6-二甲基吡啶/
• Copper Catalysts for Selective CC Bond Cleavage of β-O-4 Lignin Model Compounds
  作者：Baburam Sedai、R. Tom Baker

  DOI：10.1002/adsc.201400463

  日期：2014.11.24

  AbstractThe reactivity of homogeneous copper catalysts towards the selective CC bond cleavage of both phenolic and non‐phenolic arylglycerol β‐aryl ether lignin model compounds has been explored. Several copper precursors, nitrogen ligands, and solvents were evaluated in order to optimize the catalyst system. Using the optimized catalyst system, copper(I) trifluoromethanesulfonate [Cu(OTf)]/L/TEMPO (L=2,6‐lutidine, TEMPO=2,2,6,6‐tetramethyl‐piperidin‐1‐yl‐oxyl), aerobic oxidation of the non‐phenolic β‐O‐4 lignin model compound proceeded with good selectivity for CαCβ bond cleavage, affording 3,5‐dimethoxybenzaldehyde as the major product. Aerobic oxidation of the corresponding phenolic β‐O‐4 lignin model proceeded with different selectivity, affording 2,6‐dimethoxybenzoquinone and α,β‐unsaturated aldehyde products resulting from cleavage of the CαCaryl bond. At low catalyst concentrations, however, a change in selectivity was observed as oxidation of the benzylic secondary alcohol predominated with both substrates.magnified image