79629-17-7

Upstream product

• 95485-29-3 Dimethyl (4-Methyl-2-oxo-3-pentenyl)phosphonate 
• 100-52-7 benzaldehyde 
• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 
• 102-92-1 Cinnamoyl chloride 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 67-64-1 acetone 
• 300708-87-6 ((E)-2-oxo-4-phenylbut-3-enyl)phosphonic acid dimethyl ester 
• 104-54-1 3-Phenylpropenol 
• 563-47-3 3-Chloro-2-methylpropene 
• 104-55-2 3-phenyl-propenal 
• 773892-46-9 2-bromo-3-phenyl-4,4-dimethylcyclopentan-1-one 
• 588-72-7 [(E)-2-bromoethenyl]benzene 

Downstream Products

• 74966-39-5 2,2-dimethyl-cis-6-phenylselenan-r-4-ol 
• 74966-43-1 2,2-dimethyl-trans-6-phenylselenan-r-4-ol 
• 1254705-73-1 C₁₈H₂₂O₅ 
• 1254705-71-9 dimethyl 2,2-dimethyl-4-oxo-6-phenylcyclohexane-1,1-dicarboxylate 
• 74966-34-0 2,2-dimethyl-6-phenyl-4-selenanone 

Relevant academic research and scientific papers

Intramolecular Hetero-Michael addition of ss-hydroxyenones for the preparation of highly substituted tetrahydropyranones

Structurally diverse ss-hydroxyenones are shown to undergo nonoxidative 6-endo-trig ring closure to form highly substituted tetrahydropyranones. Amberlyst-15, Al(C1O4) 3·9H2O and [Pd(MeCN)4](BF 4)sub

Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: Chloride compensates for π-complex instability

Methallyl chloride serves as an efficient allyl donor in highly enantioselective Grignard Nozaki-Hiyama methallylations from the alcohol or aldehyde oxidation level via iridium catalyzed transfer hydrogenation. Under identical conditions, methallyl acetat

Stereoselective synthesis of cyclohexanones via phase transfer catalyzed double addition of nucleophiles to divinyl ketones

Functionalized cyclohexanones are formed in excellent yield and diastereoselectivity from a phase transfer catalyzed double addition of active methylene pronucleophiles to nonsymmetrical divinyl ketones.

A novel and efficient stereo-controlled synthesis of hexahydroquinolinones via the diene-transmissive hetero-Diels-Alder reaction of cross-conjugated azatrienes with ketenes and electrophilic dienophiles

The diene-transmissive hetero-Diels-Alder (DTHDA) reactions of cross-conjugated azatrienes (divinylimines or penta-1,4-dien-3-imines) having an N-aryl, N-alkyl, or N-dimethylamino substituent have been examined. The initial reaction of the azatrienes with diphenylketene at room temperature yielded β-lactams of [2+2] cycloadducts, which upon heating underwent [1,3]-sigmatropic rearrangement to produce the formal [4+2] cycloadducts. The reaction of N-phenylazatriene with dimethylketene or dichloroketene produced the [2+2] cycloadducts only, while the reaction of N-(dimethylamino)azatriene with dichloroketene gave the [4+2] cycloadduct without heating. When the [2+2] cycloadduct has two different vinyl substituents at C-4 of the β-lactam ring, the regioselectivity of the rearrangement depends on steric factors and the electronic demand of the substituents. The second Diels-Alder reaction of the initial [4+2] cycloadducts with electron-deficient dienophiles (TCNE, N-phenylmaleimide) stereoselectively yielded hexahydroquinolinone derivatives. Similarly, a tandem intermolecular-intramolecular mode of the aza-DTHDA reactions produced tetracyclic nitrogen-containing heterocycles in a regio- and stereoselective manner.

Combined computational and experimental studies of the mechanism and scope of the retro-Nazarov reaction

Density functional theory calculations (B3LYP/6-31+G*) demonstrate that conjugating and electron-donating substituents at carbons three and four of a cyclopentenyl oxyallylic cation should have a rate-accelerating effect on the retro-Nazarov reactions of these species. The retro-Nazarov reaction of these intermediates is predicted to exhibit significant torquoselectivity when carbon three is substituted with a methoxy and a methyl group. Experimental studies show that oxyallylic cations can undergo effective retro-Nazarov reactions when two alkyl and one aryl/vinyl groups are on carbons three and four. An equal number of alkyl substituents or a single aryl substituent is not effective in promoting the reaction. Interestingly, a single alkoxy substituent at carbon three is sufficient for the retro-Nazarov reaction to occur. The methodology developed was used in a total synthesis of the natural product turmerone.

1,8-diazabicyclo[5.4.0]undec-7-ene: A remarkable base in the epoxidation of α,β-unsaturated-δ-lactones and other enones with anhydrous t-BuOOH

1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) has been studied for the epoxidation of electron deficient alkenes with anhydrous t-BuOOH (TBHP) in dichloroethane. Steric demands are higher than that for alkaline H2O2 DBU is recognised as a remarkable base in these oxidations as other bases such as triethyl amine, diisopropylethyl amine, and 1,4-diazabicyclo[2.2.2]octane (DABCO) are absolutely inefficient. DBU is effective in promoting the oxidation of α,β-unsaturated δ-lactones where most of conventional methods either fail or perform poor.

Nazarov Reaction of Trisubstituted Dienones: Mechanism Involving Wagner-Meerwein Shift

The Nazarov reactions of trisubstituted α,α'-dienones were studied.Whereas α,β-dimethyl-β'-alkyl α,α'-dienones gave 2,3-dimethyl-4-alkyl-2-cyclopentenones when heated in concentrated sulfuric acid, the reaction of β,β-dimethyl-β'-alkyl α,α'-dienones afforded 3,4-dimethyl-4-alkyl-2-cyclopentenones as the rearranged products.A mechanistic investigation using two deuterated dienones suggests that the Nazarov reactions of the latter dienones are accompanied by Wagner-Meerwein shifts to form the most stable carbocations.

Metallic Nickel-Mediated Synthesis of Ketones by the Reaction of Benzylic, Allylic, Vinylic, and Pentafluorophenyl Halides with Acid Halides

Metallic nickel was investigated as a convenient coupling reagent for the synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides at 85 deg C in glyme.A variety of benzylic ketones with functional groups including halogen, cyano, methoxycarbonyl, and hydroxycarbonyl groups were prepared in good yields by this method.The reaction was demonstrated to proceed via organonickel halide intermediates formed by the smooth oxidative addition of benzylic and acyl halides to metallic nickel, which were trapped with electron-deficient olefins. (?-Allyl)nickel halides, prepared in situ at 85 deg C from allylic halides and the nickel, also worked for the preparation of ketones.Vinylic and pentafluorophenyl halides but not alkyl halides reacted with acid halides to give the corresponding ketones in moderate yields.