cyclohexanone enolate | 155069-25-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexanone enolate
• 英文别名: cyclohexanone; enolate；cyclohexanone enolate anion；Cyclohexen-1-olate
• CAS: 155069-25-3
• 化学式: C₆H₉O
• 分子量: 97.1369
• InChiKey: QHDHNVFIKWGRJR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-碘苄胺 、 cyclohexanone enolate 在 sodium tetrahydroborate 、 氢气 作用下， 生成 1,2,3,4-tetrahydrophenanthridine
  参考文献：
  名称：

  Studies on SRN1 reactions-9

  摘要：

  DOI：

  10.1016/s0040-4020(01)91177-9
• 作为产物：
  描述：

  2-环己烯-1-酮 、 以 gas 为溶剂， 296.0 ℃ 、53.33 Pa 条件下， 生成 cyclohexanone enolate 、 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  1,2-Versus 1,4-reduction of α,β-unsaturated carbonyl compounds in the gas phase

  摘要：

  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.

  DOI：

  10.1002/oms.1210281243

文献信息

• Alkylation of enolate ions
  作者：Mark E. Jones、Steven R. Kass、Jonathan Filley、Robert M. Barkley、G. Barney Ellison

  DOI：10.1021/ja00287a019

  日期：1985.1

  Description d'une procedure pour etudier la chimie ion-molecule en phase gazeuse dans laquelle les produits de reaction neutres sont collectes et identifies. Application a l'etude de la reaction de l'enolate de la cyclohexanone avec le bromomethane qui conduit seulement au produit d'O-alkylation

  描述 d'une procedure pour etudier la chimie ion-molecule en phasegazeuse dans laquelle les produits de reaction neutres sont collectes et识别。应用 a l'etude de la 反应 de l'enolate de la cyclohexanone avec le bromethane qui导管 seulement au produit d'O-烷基化
• Gas-phase Broensted versus Lewis acid-base reactions of 6,6-dimethylfulvene. A sensitive probe of the electronic structures of organic anions
  作者：Mark D. Brickhouse、Robert R. Squires

  DOI：10.1021/ja00217a002

  日期：1988.4
• Die Michael-Addition von Enolaten und Enaminaten an 2-(<i>N</i>-Methylanilino)-acrylonitril. Eine einfache und vielseitige Synthese von 1,4-Dicarbonyl-Verbindungen
  作者：Hubertus Ahlbrecht、Klaus Pfaff

  DOI：10.1055/s-1980-29044

  日期：——
• The SRN1 Reaction: An Attempt to Calculate the Thermodynamic Driving Force for the Addition of Nucleophiles to Phenyl Radical.
  作者：Carlo Galli、Patrizia Gentili、Lian Zhang、Björn Åkermark、John H. Wagenknecht、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0067

  日期：——

  Phenyl radical is formed in the propagation chain of the aromatic SRN 1 reaction from cleavage of the radical anion of the precursor phenyl halide (PhX.-); subsequent addition of nucleophile Y- to Ph-. yields the radical anion of the substitution product (PhY.-). In this addition step, transfer of an electron from the nucleophile to Ph-. is concerted with bond formation, and the extra electron of the new two-center three-electron bond is, in general, located in a pi* MO of the aromatic moiety. Three factors mainly affect the efficiency of this addition step: (i) the energy of the new Ph-Y bond; (ii) the stability of the radical anion of the substitution product; (iii) the oxidation potential of the nucleophile. In keeping with these points, the energy of some Ph-Y bonds has been calculated, and the oxidation potential of Y- species, along with the reduction potential of the related PhY substitution products, have been determined. Calculation of the thermodynamic driving force of the nucleophile/radical addition step is reported for some significant nucleophiles. Finally, comparison of the thermodynamic driving force with experimental reactivity of the same nucleophile in the addition step is attempted.