Methyl (2,4-dimethoxybenzoyl)formate | 99865-93-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl (2,4-dimethoxybenzoyl)formate
• 英文别名: methyl 2,4-dimethoxyphenylglyoxylate；(2,4-dimethoxy-phenyl)-glyoxylic acid methyl ester；(2,4-Dimethoxy-phenyl)-glyoxylsaeure-methylester；Methyl (2,4-dimethoxyphenyl)(oxo)acetate；methyl 2-(2,4-dimethoxyphenyl)-2-oxoacetate
• CAS: 99865-93-7
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: NIPMNYAYTGCSET-UHFFFAOYSA-N

物化性质

• 沸点：
  353.2±32.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl (2,4-dimethoxybenzoyl)formate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 Methyl 2,4-dimethoxymandelate
  参考文献：
  名称：

  Photochemistry of Substituted Benzoylformate Esters. A Convenient Method for the Photochemical Oxidation of Alcohols

  摘要：

  The production of aldehydes and ketones via photochemical hydrogen atom transfer in substituted benzoylformate esters of primary and secondary alcohols has been investigated. Substituent effect studies have shown that (2,4-dimethoxybenzoyl)formate (DMBF) esters give superior performance. A divergence in the byproducts derived from the ester group (the benzaldehyde (and presumably CO) or the benzoic acid (and presumably CO2)) is observed depending on the presence of oxygen. A mechanistic rationale for the formation of the benzoic acid has been advanced based on the known trapping of intermediate 1,4-biradicals by oxygen followed by fragmentation.

  DOI：

  10.1021/jo00113a029
• 作为产物：
  描述：

  2,4-Dihydroxybenzoylformic acid 生成 Methyl (2,4-dimethoxybenzoyl)formate
  参考文献：
  名称：

  Hargreaves et al., Journal of Applied Chemistry, 1958, vol. 8, p. 273,280

  摘要：

  DOI：

文献信息

• Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates
  作者：Sunewang R. Wang、Jiru Shao、Caiyun An

  DOI：10.1055/a-1526-7839

  日期：2021.11

  -aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C–C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.

  报道了一种从容易获得的 2-酰基环丙烷-1-芳基-1-羧酸酯通过 TfOH 介导多取代 2-吡喃酮的简便途径。强供体 1-芳基对于指导供体-受体环丙烷环的 C-C 键断裂很重要，然后通过内酯化形成 2-吡喃酮环。
• Vilsmeier formylation and glyoxylation reactions of nucleophilic aromatic compounds using pyrophosphoryl chloride
  作者：Ian M. Downie、Martyn J. Earle、Harry Heaney、Khamis F. Shuhaibar

  DOI：10.1016/s0040-4020(01)89915-4

  日期：1993.5

  that undergo reactions with a wide range of nucleophilic aromatic substrates, including indoles, pyrroles, thiophenes, furans, and methoxy-substituted carbocyclic arenes to afford, after hydrolysis of the initial products, good to excellent yields of the expected aldehydes; reactions with methyl oxamates allow the preparation of methyl arylglyoxylates.

  N，N-二甲基甲酰胺和N-甲基甲酰苯胺与焦磷酰氯的反应导致形成与多种亲核芳香族底物发生反应的试剂，包括吲哚，吡咯，噻吩，呋喃和甲氧基取代的碳环芳烃，初始产物水解后，预期醛的收率好至极好；与草酸甲酯反应可以制备芳基乙醛酸甲酯。