2-Hydroxy-2-(2,3-dimethoxyphenyl)-1-phenylethanone | 74552-56-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-Hydroxy-2-(2,3-dimethoxyphenyl)-1-phenylethanone
• 英文别名: 2-(2,3-Dimethoxyphenyl)-2-hydroxy-1-phenylethanone
• CAS: 74552-56-0
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: WYKWQRQQPXYCSQ-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  432.5±45.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Hydroxy-2-(2,3-dimethoxyphenyl)-1-phenylethanone 在 sodium dichromate 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 2,3-Dimethoxy-benzil
  参考文献：
  名称：

  酮取代三邻苯二酚钛(IV)配合物单体-二聚体平衡的溶剂依赖性

  摘要：

  基于酮取代三邻苯二酚钛(IV)的多级螺旋化合物根据不同的溶剂表现出不同的单体-二聚体行为。分析了一系列不同烷基取代的配合物的二聚常数，表明溶剂对二聚有很强的影响。因此，诸如疏溶剂性/亲和性、空间立体、取代基的电子性和弱侧链-侧链相互作用等效应似乎协同作用。

  DOI：

  10.1002/chem.202001053
• 作为产物：
  描述：

  2-diethylphosphoryloxy-2-(2,3-dimethoxyphenyl)-1-phenylethanone 在 二乙胺 作用下， 以 水 为溶剂， 以56%的产率得到2-Hydroxy-2-(2,3-dimethoxyphenyl)-1-phenylethanone
  参考文献：
  名称：

  氰化物催化的醛到醛的加成反应：苯偶姻型反应的新的酰基供体

  摘要：

  酰基膦酸酯已被用作氰化物催化的安息香型反应的新的酰基供体。酰基膦酸酯的氰化，然后是[1,2]-磷酰基迁移，生成了活性的酰基阴离子中间体。推测的（氰基）磷酸根阴离子与各种芳基醛反应，生成磷酸酯保护的不对称安息香，收率良好至极佳。在用胺水溶液使磷酸酯脱保护后，可以获得不对称的安息香产物。

  DOI：

  10.1002/adsc.200505097

文献信息

• Photoremovable Protecting Groups for Phosphorylation of Chiral Alcohols. Asymmetric Synthesis of Phosphotriesters of (-)-3',5'-Dimethoxybenzoin
  作者：Michael C. Pirrung、Steven W. Shuey

  DOI：10.1021/jo00093a021

  日期：1994.7

  Procedures have been developed for the preparation of dimethoxybenzoinyl (DMB) phosphate triesters that can be deprotected photochemically. These compounds can be useful in light-directed synthesis and caging. The photochemistry of a wide variety of fluorine-, oxygen-, and nitrogen-substituted benzoin acetates was examined to determine the substitution pattern in the nonacylated aromatic ring producing optimum chemical yields. Two groups, 2',3'-dimethoxybenzoin and 3',5'dimethoxybenzoin, were found to give the highest yields of the benzofuran product and were further developed for the photochemical deprotection of phosphate esters. These reactions could not be quenched, suggesting a singlet photosolvolysis mechanism. An asymmetric synthesis of 3',5'dimethoxybenzoin via the benzaldehyde cyanohydrin was developed that minimizes the number of diastereomers formed in the phosphorylation of chiral alcohols. A phosphoramidite reagent for the derivatization of alcohols was prepared and used to produce scalemic dimethoxybenzoinyl phosphate esters from pantolactone and glycerol, serine, and tyrosine derivatives. These compounds were deprotected photochemically to produce the phosphodiesters in high yield.
• .alpha.-Heterosubstituted phosphonate carbanions. 11. Benzoins via an acyl anion equivalent. Novel one-pot preparation of benzo[b]furans via benzoins using hydriodic acid
  作者：Rusty E. Koenigkramer、Hans Zimmer

  DOI：10.1021/jo01308a009

  日期：1980.9
• KOENIGKRAMER R. E.; ZIMMER H., J. ORG. CEM., 1980, 45, NO 20, 3994-3998
  作者：KOENIGKRAMER R. E.、 ZIMMER H.

  DOI：——

  日期：——
• Solvent Dependence of the Monomer–Dimer Equilibrium of Ketone‐Substituted Triscatecholate Titanium(IV) Complexes
  作者：A. Carel N. Kwamen、Judith Jenniches、Iris M. Oppel、Markus Albrecht

  DOI：10.1002/chem.202001053

  日期：2020.8.17

  Hierarchical helicates based on ketone‐substituted titanium(IV)triscatecholates show different monomer‐dimer behavior depending on different solvents. The dimerization constants of a whole series of differently alkyl‐substituted complexes is analyzed to show that the solvent has a very strong influence on the dimerization. Hereby, effects like solvophobicity/philicity, sterics, electronics of the substituents

  基于酮取代三邻苯二酚钛(IV)的多级螺旋化合物根据不同的溶剂表现出不同的单体-二聚体行为。分析了一系列不同烷基取代的配合物的二聚常数，表明溶剂对二聚有很强的影响。因此，诸如疏溶剂性/亲和性、空间立体、取代基的电子性和弱侧链-侧链相互作用等效应似乎协同作用。
• Cyanide-Catalyzed Additions of Acyl Phosphonates to Aldehydes: A New Acyl Donor for Benzoin-Type Reactions
  作者：Cory C. Bausch、Jeffrey S. Johnson

  DOI：10.1002/adsc.200505097

  日期：2005.7

  phosphonates, followed by a [1,2]-phosphoryl migration generates the active acyl anion intermediate. The presumed (cyano)phosphate anion reacts with a variety of aryl aldehydes to yield phosphate ester-protected, unsymmetrical benzoins in good to excellent yields. The unsymmetrical benzoin product can be obtained after deprotection of the phosphate ester with an aqueous amine solution.

  酰基膦酸酯已被用作氰化物催化的安息香型反应的新的酰基供体。酰基膦酸酯的氰化，然后是[1,2]-磷酰基迁移，生成了活性的酰基阴离子中间体。推测的（氰基）磷酸根阴离子与各种芳基醛反应，生成磷酸酯保护的不对称安息香，收率良好至极佳。在用胺水溶液使磷酸酯脱保护后，可以获得不对称的安息香产物。