potassium enolate of acetophenone | 15480-89-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: potassium enolate of acetophenone
• 英文别名: Potassium;1-phenylethenolate
• CAS: 15480-89-4
• 化学式: C₈H₇O*K
• 分子量: 158.241
• InChiKey: FPTYPTBPKIQSPF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  potassium enolate of acetophenone 在 CO 作用下， 以 四氢呋喃 、 氘代苯 为溶剂， 生成
  参考文献：
  名称：

  Slough, Greg A.; Hayashi, Randy; Ashbaugh, John R., Organometallics, 1994, vol. 13, # 3, p. 890 - 898

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 生成 potassium enolate of acetophenone
  参考文献：
  名称：

  S_RN1 Photostimulated Reaction of Triphenylvinyl Bromide with Carbanions in DMSO

  摘要：

  DOI：

  10.1021/jo951144c

文献信息

• Mechanism of the carbon-carbon cleavage of acetone by the ruthenium benzyne complex (PMe3)4Ru(.eta.2-C6H4): formation and reactivity of an oxametallacyclobutane complex
  作者：John F. Hartwig、Robert G. Bergman、Richard A. Andersen

  DOI：10.1021/ja00164a067

  日期：1990.4

  Generation et caracterisation d'un intermediaire potentiel de la reaction, le complexe (methyl-4 phenyl-4)oxa-1 ruthena-2 cyclobutane

  Generation et caracterisation d'un intermediaire potentiel de la reaction, le complexe (methyl-4 phenyl-4)oxa-1 ruthena-2 cyclobutane
• Ambient-Temperature Carbon–Oxygen Bond Cleavage of an α-Aryloxy Ketone with Cp₂Ti(BTMSA) and Selective Protonolysis of the Resulting Ti–OR Bonds
  作者：Addison N. Desnoyer、Beata Fartel、K. Cory MacLeod、Brian O. Patrick、Kevin M. Smith

  DOI：10.1021/om300950c

  日期：2012.11.12

  Reaction of Cp2Ti[η2-(CSiMe3)2] with an α-aryloxy ketone produces a Ti(IV) enolate aryloxide complex. Selective protonolysis of the enolate ligand or both Ti–OR bonds can be achieved with various acids. The reaction of the enolate aryloxide with 1-phenyl-2-phenoxyethanol is catalyzed by a mixture of NEt3 and [HNEt3]X (X = OTf, BPh4).

  Cp的反应2的Ti [η 2 - （CSiMe 3）2 ]与α-芳氧基酮产生的Ti（IV）烯醇芳复杂。烯醇盐配体或两个Ti-OR键的选择性质子分解可以通过各种酸实现。NEt 3和[HNEt 3 ] X（X = OTf，BPh 4）的混合物催化烯醇盐的芳氧化物与1-苯基-2-苯氧基乙醇的反应。
• Mechanism of Catalytic Oxidation of Styrenes with Hydrogen Peroxide in the Presence of Cationic Palladium(II) Complexes
  作者：Katherine L. Walker、Laura M. Dornan、Richard N. Zare、Robert M. Waymouth、Mark J. Muldoon

  DOI：10.1021/jacs.7b05413

  日期：2017.9.13

  Kinetic studies, isotope labeling, and in situ high-resolution mass spectrometry are used to elucidate the mechanism for the catalytic oxidation of styrenes using aqueous hydrogen peroxide (H2O2) and the cationic palladium(II) compound, [(PBO)Pd(NCMe)2][OTf]2 (PBO = 2-(pyridin-2-yl)benzoxazole). Previous studies have shown that this reaction yields acetophenones with high selectivity. We find that

  动力学研究、同位素标记和原位高分辨率质谱用于阐明使用过氧化氢 (H2O2) 水溶液和阳离子钯 (II) 化合物 [(PBO)Pd(NCMe) 催化氧化苯乙烯的机制2][OTf]2 (PBO = 2-(吡啶-2-基)苯并恶唑)。先前的研究表明，该反应可以高选择性地产生苯乙酮。我们发现 H2O2 与 Pd(II) 结合，然后与苯乙烯结合以生成 Pd-烷基过氧化物，该过氧化物至少通过两个竞争过程释放苯乙酮，其中一个过程涉及钯烯醇化物中间体，此前在烯烃氧化反应中未观察到该中间体。我们建议苯乙酮是由钯烯醇中间体通过 H2O2 质子化形成的。我们用叔丁基过氧化氢代替过氧化氢，发现，
• Novel photoinduced carbon-carbon bond formation in purines
  作者：Vasu Nair、Stanley D. Chamberlain

  DOI：10.1021/ja00293a066

  日期：1985.4

  Reactions S RN1 entre l'ethyl-9 iodo-6 purine et l'enolate de diverses cetones. Mecanismes

  反应 S RN1 进入 l'ethyl-9 iodo-6 purine et l'enolate de differents cetones。机制
• Structure and reactions of oxametallacyclobutanes and oxametallacyclobutenes of ruthenium
  作者：John F. Hartwig、Robert G. Bergman、Richard A. Andersen

  DOI：10.1021/om00055a061

  日期：1991.9

  Structure and reactivity studies are reported with the ruthenium metallacycles prepared as described in the previous paper. A C-C cleavage reaction by an apparent beta-Me elimination pathway at 45-degrees-C is reported for the PMe3-substituted oxametallacyclobutane complex (PMe3)4Ru(OC(Me)(Ph)CH2) (1), while the analogous DMPE-substituted metallacyclobutane (DMPE)2Ru(OC(Me)(Ph)CH2) (2) is stable at 140-degrees-C. Similarly, compound 1 undergoes insertion of CO into the metal-carbon bond, while 2 is inert toward this substrate. Addition of protic acids and electrophiles leads to rapid extrusion of alpha-methylstyrene with both metallacycles. X-ray structural analysis of the acetone dianion complex (PMe3)4Ru((CH2)2CO) (17) was performed and displays a dihedral angle of 46-degrees-C in the metallacycle. In contrast, the 4,4-dimethyl-2-butanone dianion complex (PMe3)4Ru(CH2C(CHCMe3)O) (15) contains a flat metallacycle that is bound through the CH2 group and the oxygen atom. Reactivity studies with 15 showed that, unlike compounds 1 and 2, the organic portion remained intact upon addition of protic acids. The addition of 4,4-dimethyl-2-butanone led to a second C-C cleavage reaction, forming the di-tert-butylacetylacetonate complex (PMe3)3Ru(Me)(CH(COCH2CMe3)2) (19). Reactivity studies with 17 showed reversible formation of the isolable oxatrimethylenemethane complex 18, which was isolated and structurally characterized. Addition of acetone to 17 led to formation of mesityl oxide dianion complex (PMe3)4Ru(OC(Me)CHC(Me)CH) (19); mesityl oxide is presumably formed by aldol condensation at the metal center. Reactivity studies of the oxametallacyclobutene complex (PMe3)4Ru(OC(CMe3)CH) showed formation of free ketone upon addition of protic acids and insertion into the metal-oxygen bond upon addition of CO2. The metallacycle was converted to the silyl enol ether upon addition of trimethylsilane and to the free ketone following addition of H-2.