1-pyrenylmethyl methylmalonate monoester

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1-pyrenylmethyl methylmalonate monoester
• 英文别名: 2-Methyl-3-oxo-3-(pyren-1-ylmethoxy)propanoic acid；2-methyl-3-oxo-3-(pyren-1-ylmethoxy)propanoic acid
• 化学式: C₂₁H₁₆O₄
• 分子量: 332.356
• InChiKey: WXPGEXVZOJEUQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 1-pyrenylmethyl methylmalonate monoester 生成 2-Methyl-malonic acid methyl ester pyren-1-ylmethyl ester
  参考文献：
  名称：

  Formation in an aqueous matrix and properties and chromatographic behavior of 1-pyrenyldiazomethane derivatives of methylmalonic acid and other short-chain dicarboxylic acids

  摘要：

  Methylmalonic acid (MMA) and some short-chain dicarboxylic acids were derivatized with the fluorescent labeling reagent 1-pyrenyldiazomethane (PDAM) in an aqueous matrix. The derivatization of MMA and ethylmalonic acid (EMA) proceeded and leveled off rapidly at low pH, whereas at alkaline pH, the fluorescent derivative was progressively formed over a period of more than 24 h, and higher fluorescence yield was obtained. The PDAM esters of MMA and EMA had an excitation maximum at 340 mm and emission maxima at 376 and 395 mm. They were stable for days in aqueous media at room temperature. The MMA derivative was identified as 1-pyrenylmethyl methylmalonate monoester by mass spectrometry, and formation of 1-pyrenylmethyl methylmalonate diester could not be demonstrated. The free carboxylic acid moiety and the ionization of this group may explain the unique chromatographic properties of the MMA derivative, i.e. a marked increase in the capacity factor in a reversed-phase system by decreasing the pH of the mobile phase. The MMA derivative was separated from PDAM esters of several other short-chain dicarboxylic acids by a acetonitrile gradient in formate buffer, pH 2.5. These data may form the basis for the construction of automated MMA assays involving derivatization in aqueous media followed by liquid chromatography.

  DOI：

  10.1021/ac00027a013
• 作为产物：
  描述：

  甲基丙二酸 、 1-芘基二氮杂甲烷 生成 1-pyrenylmethyl methylmalonate monoester
  参考文献：
  名称：

  Formation in an aqueous matrix and properties and chromatographic behavior of 1-pyrenyldiazomethane derivatives of methylmalonic acid and other short-chain dicarboxylic acids

  摘要：

  Methylmalonic acid (MMA) and some short-chain dicarboxylic acids were derivatized with the fluorescent labeling reagent 1-pyrenyldiazomethane (PDAM) in an aqueous matrix. The derivatization of MMA and ethylmalonic acid (EMA) proceeded and leveled off rapidly at low pH, whereas at alkaline pH, the fluorescent derivative was progressively formed over a period of more than 24 h, and higher fluorescence yield was obtained. The PDAM esters of MMA and EMA had an excitation maximum at 340 mm and emission maxima at 376 and 395 mm. They were stable for days in aqueous media at room temperature. The MMA derivative was identified as 1-pyrenylmethyl methylmalonate monoester by mass spectrometry, and formation of 1-pyrenylmethyl methylmalonate diester could not be demonstrated. The free carboxylic acid moiety and the ionization of this group may explain the unique chromatographic properties of the MMA derivative, i.e. a marked increase in the capacity factor in a reversed-phase system by decreasing the pH of the mobile phase. The MMA derivative was separated from PDAM esters of several other short-chain dicarboxylic acids by a acetonitrile gradient in formate buffer, pH 2.5. These data may form the basis for the construction of automated MMA assays involving derivatization in aqueous media followed by liquid chromatography.

  DOI：

  10.1021/ac00027a013

文献信息

• Formation in an aqueous matrix and properties and chromatographic behavior of 1-pyrenyldiazomethane derivatives of methylmalonic acid and other short-chain dicarboxylic acids
  作者：Jorn. Schneede、Per Magne. Ueland

  DOI：10.1021/ac00027a013

  日期：1992.2.1

  Methylmalonic acid (MMA) and some short-chain dicarboxylic acids were derivatized with the fluorescent labeling reagent 1-pyrenyldiazomethane (PDAM) in an aqueous matrix. The derivatization of MMA and ethylmalonic acid (EMA) proceeded and leveled off rapidly at low pH, whereas at alkaline pH, the fluorescent derivative was progressively formed over a period of more than 24 h, and higher fluorescence yield was obtained. The PDAM esters of MMA and EMA had an excitation maximum at 340 mm and emission maxima at 376 and 395 mm. They were stable for days in aqueous media at room temperature. The MMA derivative was identified as 1-pyrenylmethyl methylmalonate monoester by mass spectrometry, and formation of 1-pyrenylmethyl methylmalonate diester could not be demonstrated. The free carboxylic acid moiety and the ionization of this group may explain the unique chromatographic properties of the MMA derivative, i.e. a marked increase in the capacity factor in a reversed-phase system by decreasing the pH of the mobile phase. The MMA derivative was separated from PDAM esters of several other short-chain dicarboxylic acids by a acetonitrile gradient in formate buffer, pH 2.5. These data may form the basis for the construction of automated MMA assays involving derivatization in aqueous media followed by liquid chromatography.