methyl vinyl ketone enolate anion | 130336-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl vinyl ketone enolate anion
• CAS: 130336-62-8
• 化学式: C₄H₅O
• 分子量: 69.0831
• InChiKey: YNAOPTIRNRNSPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  5.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  1-vinylcyclobutoxide 生成 乙烯 、 methyl vinyl ketone enolate anion
  参考文献：
  名称：

  气相中的单分子重排和断裂：[1,3] Sigmatropic 异构化和 [2 + 2] Cycloreversions

  摘要：

  3-丁烯-2-醇、1-乙烯基环丙醇、1-乙烯基环丁醇和环丁醇的三甲基甲硅烷醚在变温流动余辉三重四极杆装置中在很宽的温度范围（–40 至 300°C）内用氟化物处理。通过离子-分子反应及其碰撞诱导解离 (CID) 光谱探测所得醇盐和烯醇化物的结构。获得了几个阴离子加速的[1,3] sigmatropic 重排和[2 + 2] 环回复的活化能。讨论了这些异构化和碎片化（逐步与协同）的机制及其合成潜力。

  DOI：

  10.1071/ch03002

文献信息

• Carbanion rearrangements. Collision-induced dissociations of the enolate ion of heptan-4-one
  作者：Michael B. Stringer、John H. Bowie、John L. Holmes

  DOI：10.1021/ja00274a005

  日期：1986.7

  Le mecanisme de formation des principaux ions negatifs obtenus dans le schema de fragmentation de l'ion du titre est etudie en utilisant une serie de composes marques D et 13 C

  Le mecanisme deformation des principaux ions negatifs obtenus dans le schema de fragmentation de l'ion du titre est etudie en utilisant une serie de composes marques D et 13 C
• Hypovalent radicals. 8. Identification of nucleophilic 1,2- and 1,4-addition processes with .alpha.,.beta.-unsaturated molecules in the gas phase
  作者：Richard N. McDonald、A. Kasem Chowdhury

  DOI：10.1021/ja00539a031

  日期：1980.9
• 1,2-Versus 1,4-reduction of α,β-unsaturated carbonyl compounds in the gas phase
  作者：Yeunghaw Ho、Robert R. Squires

  DOI：10.1002/oms.1210281243

  日期：1993.12

  AbstractThe regioselectivity involved in the gas‐phase hydride reduction of α,β‐unsaturated carbonyl compounds by pentacoordinate silicon hydride ions is investigated. The kinetics and product distributions of the reactions of acrolein, methyl vinyl ketone and cyclohex‐2‐enone with monoalkoxysiliconate ions of the general composition RSiH3(OR′)− were examined with the flowing afterglow–triple quadrupole technique. All three substrates react by hydride transfer and by formation of a siliconate adduct in which hydride reduction of the organic reactant has occurred. The structures of these adducts and the hydride transfer products were identified by various tandem mass spectrometric protocols, including analysis of competitive collision‐induced dissociation (CID) reactions and comparisons of CID spectra obtained from reference ions with known structures. 1,4‐Reduction forming an enolate ion product is found to be the dominant or exclusive process with all three substrates, i.e. acrolein (70 ± 5%), methyl vinyl ketone (72 ± 5%) and cyclohex‐2‐enone (100%). Comparisons are made between these gas‐phase results and the regioselectivity reported for analogous condensed‐phase reactions. The observed behavior is discussed in terms of the reaction thermochemistry.
• Unimolecular Rearrangements and Fragmentations in the Gas Phase: [1,3] Sigmatropic Isomerizations and [2 + 2] Cycloreversions
  作者：Mohammad R. Ahmad、Steven R. Kass

  DOI：10.1071/ch03002

  日期：——

  alkoxides and enolates were probed by ion–molecule reactions and their collision-induced dissociation (CID) spectra. Activation energies were obtained for several anion-accelerated [1,3] sigmatropic rearrangements and [2 + 2] cycloreversions. The mechanisms for these isomerizations and fragmentations (stepwise versus concerted) and their synthetic potential are discussed.

  3-丁烯-2-醇、1-乙烯基环丙醇、1-乙烯基环丁醇和环丁醇的三甲基甲硅烷醚在变温流动余辉三重四极杆装置中在很宽的温度范围（–40 至 300°C）内用氟化物处理。通过离子-分子反应及其碰撞诱导解离 (CID) 光谱探测所得醇盐和烯醇化物的结构。获得了几个阴离子加速的[1,3] sigmatropic 重排和[2 + 2] 环回复的活化能。讨论了这些异构化和碎片化（逐步与协同）的机制及其合成潜力。