1,3-Dioxolan-2-ylidene(methyl)oxidanium | 101418-99-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Dioxolan-2-ylidene(methyl)oxidanium
• CAS: 101418-99-9
• 化学式: C₄H₇O₃
• 分子量: 103.098
• InChiKey: FDZKNFCEUXEKME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  19.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-Dioxolan-2-ylidene(methyl)oxidanium 在 水 作用下， 生成 2-Methoxy-[1,3]dioxolan-2-ol
  参考文献：
  名称：

  Radiation-chemical production and lifetimes of trialkoxymethyl carbocations in aqueous solution

  摘要：

  DOI：

  10.1021/ja00271a004
• 作为产物：
  描述：

  2,2-Dimethoxy-1,3-dioxolane 在 硫酸 作用下， 生成 1,3-Dioxolan-2-ylidene(methyl)oxidanium
  参考文献：
  名称：

  Radiation-chemical production and lifetimes of trialkoxymethyl carbocations in aqueous solution

  摘要：

  DOI：

  10.1021/ja00271a004

文献信息

• Gas-phase oxirane addition to acylium ions on reaction with 1,3-dioxolanes elucidated by tandem and triple stage mass spectrometric experiments
  作者：Marcos N. Eberlin、R. G. Cooks

  DOI：10.1002/oms.1210280605

  日期：1993.6

  AbstractAcylium ions containing a variety of substituents all undergo an unprecedented reaction with 1,3‐dioxolanes which gives rise to a cyclic, resonance‐stabilized oxonium ion, formally the product of oxirane (C2H4O) addition to the reagent ion. The structure for the ion–molecule product is supported by multiple‐stage mass spectrometric experiments, performed in a pentaquadrupole mass spectrometer, which show the expected fragmentation by C2H4O loss to yield the original reactant acylium ions. The oxonium ions are formed in relatively high abundance in many cases and are observed even when proton‐transfer reactions would be expected to occur competitively owing to the acidity of some of the acylium ions studied. This ion–molecule reaction is proposed to serve as a general method for identification and/or trapping of ions of the whole acylium ion class and also for the gas‐phase generation of the oxonium ions. The reaction with 1,3‐dioxolane is also useful in distinguishing the most stable C2H3O+ ion, the acetyl cation, from its two stable isomers, O‐protonated ketene and the oxiranyl cation. The thioacetyl cation, the only sulfur analog investigated, also reacts with dioxolane to form the corresponding oxirane addition product, indicating that the C2H4O addition reaction occurs and that it may be useful for identification of the thioacylium class and for the gas‐phase generation of sulfur analogs of oxonium ions.