2-Methyl-[3,3-2H2]butansaeure | 95926-93-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Methyl-[3,3-2H2]butansaeure
• CAS: 95926-93-5
• 化学式: C₅H₁₀O₂
• 分子量: 104.117
• InChiKey: WLAMNBDJUVNPJU-SMZGMGDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  7.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-Methyl-[3,3-2H2]butansaeure 在 lithium aluminium tetrahydride 、 lithium aluminium deuteride 、 氢溴酸 、 magnesium 作用下， 生成
  参考文献：
  名称：

  A Study of the Gas-Phase Reactivity of Neutral Alkoxy Radicals by Mass Spectrometry: α-Cleavages and Barton-type Hydrogen Migrations

  摘要：

  AbstractThe reactivity of neutral alkoxy radicals in the absence of any interfering intermolecular interactions is investigated by means of the recently introduced method of neutral and ion decomposition difference (NIDD) spectra. These are obtained from quantitative analysis of the corresponding neutralization–reionization (NR) and charge reversal (CR) mass spectra. The following trends emerge: alkoxy radicals with short (C1C3) or branched alkyl chains give rise to α‐cleavage products, whereas longer‐chained alkoxy radicals undergo 1,5‐hydrogen migrations from carbon to oxygen, that is, Barton‐type chemistry. This facile rearrangement has been studied in detail for n‐pentoxy radicals by isotopic labeling experiments and computation at the Becke 3 LYP/6‐31 G* level of theory. Further, the NIDD spectra of 3‐methylpentoxy radicals permit for the first time the identification of the diastereoselectivity of the gas‐phase hydrogen migrations. The results from the NIDD method are compared to those from earlier studies in the condensed phase. This new mass spectrometric approach is suggested as a tool for the examination of intramolecular reactions of free alkoxy radicals which can usefully complement theoretical studies.

  DOI：

  10.1002/chem.19970031120
• 作为产物：
  描述：

  溴乙烷-1,1-d2 、 丙酸 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 2-Methyl-[3,3-2H2]butansaeure
  参考文献：
  名称：

  A Study of the Gas-Phase Reactivity of Neutral Alkoxy Radicals by Mass Spectrometry: α-Cleavages and Barton-type Hydrogen Migrations

  摘要：

  AbstractThe reactivity of neutral alkoxy radicals in the absence of any interfering intermolecular interactions is investigated by means of the recently introduced method of neutral and ion decomposition difference (NIDD) spectra. These are obtained from quantitative analysis of the corresponding neutralization–reionization (NR) and charge reversal (CR) mass spectra. The following trends emerge: alkoxy radicals with short (C1C3) or branched alkyl chains give rise to α‐cleavage products, whereas longer‐chained alkoxy radicals undergo 1,5‐hydrogen migrations from carbon to oxygen, that is, Barton‐type chemistry. This facile rearrangement has been studied in detail for n‐pentoxy radicals by isotopic labeling experiments and computation at the Becke 3 LYP/6‐31 G* level of theory. Further, the NIDD spectra of 3‐methylpentoxy radicals permit for the first time the identification of the diastereoselectivity of the gas‐phase hydrogen migrations. The results from the NIDD method are compared to those from earlier studies in the condensed phase. This new mass spectrometric approach is suggested as a tool for the examination of intramolecular reactions of free alkoxy radicals which can usefully complement theoretical studies.

  DOI：

  10.1002/chem.19970031120

文献信息

• A Study of the Gas-Phase Reactivity of Neutral Alkoxy Radicals by Mass Spectrometry: α-Cleavages and Barton-type Hydrogen Migrations
  作者：Georg Hornung、Christoph A. Schalley、Martin Dieterle、Detlef Schröder、Helmut Schwarz

  DOI：10.1002/chem.19970031120

  日期：1997.11

  AbstractThe reactivity of neutral alkoxy radicals in the absence of any interfering intermolecular interactions is investigated by means of the recently introduced method of neutral and ion decomposition difference (NIDD) spectra. These are obtained from quantitative analysis of the corresponding neutralization–reionization (NR) and charge reversal (CR) mass spectra. The following trends emerge: alkoxy radicals with short (C1C3) or branched alkyl chains give rise to α‐cleavage products, whereas longer‐chained alkoxy radicals undergo 1,5‐hydrogen migrations from carbon to oxygen, that is, Barton‐type chemistry. This facile rearrangement has been studied in detail for n‐pentoxy radicals by isotopic labeling experiments and computation at the Becke 3 LYP/6‐31 G* level of theory. Further, the NIDD spectra of 3‐methylpentoxy radicals permit for the first time the identification of the diastereoselectivity of the gas‐phase hydrogen migrations. The results from the NIDD method are compared to those from earlier studies in the condensed phase. This new mass spectrometric approach is suggested as a tool for the examination of intramolecular reactions of free alkoxy radicals which can usefully complement theoretical studies.