丙醛烯醇阴离子 | 64724-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 丙醛烯醇阴离子
• 英文名称: propionaldehyde enolate anion
• 英文别名: n-propionaldehyde enolate；propanal enolate ion；propanal enolate；propionaldehyde; deprotonated form；prop-1-en-1-olate
• CAS: 64724-01-2
• 化学式: C₃H₅O
• 分子量: 57.0721
• InChiKey: RKMAINRIKIRXIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.41
• 重原子数：
  4.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  丙醛烯醇阴离子 在 亚硝酸丙酯 作用下， 生成
  参考文献：
  名称：

  Hayes, Roger N.; Bowie, John H.; Klass, Gunter, Journal of the Chemical Society. Perkin transactions II, 1984, # 7, p. 1167 - 1174

  摘要：

  DOI：
• 作为产物：
  描述：

  propan-1-ol; deprotonated form 生成 丙醛烯醇阴离子 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Mercer, Roger S.; Harrison, Alex G., Canadian Journal of Chemistry, 1988, vol. 66, p. 2947 - 2953

  摘要：

  DOI：

文献信息

• Studies on SRN1 reactions-9
  作者：René Beugelmans、Jacqueline Chastanet、Georges Roussi

  DOI：10.1016/s0040-4020(01)91177-9

  日期：1984.1
• Gas-phase ion-molecule reactions of phenylnitrene anion
  作者：Mark J. Pellerite、John I. Brauman

  DOI：10.1021/ja00393a033

  日期：1981.2
• Anion Structure Determination in the Gas Phase:  Chemical Reactivity as a Probe
  作者：Jeehiun K. Lee、Joseph J. Grabowski

  DOI：10.1021/jo961463j

  日期：1996.1.1

  In the gas phase, the discrimination between two isomeric anion structures is a challenge that requires different solutions for different applications. The anionic oxy-Cope rearrangement involves the rearrangement of an alkoxide to an isomeric enolate; the mechanistic study of such a process in the gas phase requires a simple and selective probe process. Using a flowing afterglow mass spectrometer, we have examined the utility and limitations of using chemical reactivity to discriminate between alkoxides and enolates in the gas phase. A series of alkoxides and enolates were allowed to react with three chemical probe reagents: methanol-O-d, methyl nitrite, and dimethyl disulfide. Quantitative and qualitative characterization of each probe reagent reveals the especially broad and flexible utility of dimethyl disulfide as a chemical probe. Dimethyl disulfide is a selective reagent with ambident behavior that reacts efficiently with all anions studied and fully capitalizes on the structure/reactivity differences between alkoxides and enolates. Alkoxides behave as classical ''hard bases'' when allowed to react with dimethyl disulfide, effecting elimination across the C-S bond, whereas enolates, ''soft bases'', attack at sulfur. Methyl nitrite is also a selective ambident probe reagent but, due to its particularly slow reaction with enolates, is useful only in conjunction with a more reliable probe such as dimethyl disulfide. Methanol-O-d, for a variety of reasons detailed in the paper, is unsuitable as a chemical probe reagent for the unequivocal discernment between alkoxides and enolates.
• 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.
• Solvent effects on ion-molecule reactions. Vinyl anions vs. conjugate addition
  作者：John E. Bartmess

  DOI：10.1021/ja00527a070

  日期：1980.3