4748-86-1

Usage

InChI:InChI=1/C8H10O/c1-7-4-2-3-5-8(7)6-9/h2-3,5-7H,4H2,1H3

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 111-92-2 dibutylamine 
• 123-73-9 crotonaldehyde 
• 64-19-7 acetic acid 
• 123-31-9 hydroquinone 
• 124-40-3 dimethyl amine 
• 109-89-7 diethylamine 
• 1515-76-0 1-acetoxy-1,3-butadiene 
• 38053-91-7 2-trimethylsilyloxy-1,3-butadiene 
• 6651-43-0 1-(trimethylsiloxy)-1,3-butadiene 
• 108-24-7 acetic anhydride 
• 82454-07-7 1-(4-Chloro-phenylselanyl)-6-methyl-cyclohex-3-enecarbaldehyde 
• 127-09-3 sodium acetate 
• 7732-18-5 water 

Downstream Products

• 34557-54-5 methane 
• 100-52-7 benzaldehyde 
• 67086-98-0 2-methyl-1-hydroxymethyl-cyclohexadiene-(4.6) 
• 112405-18-2 7-Methyl-2-phenyl-8,8a-dihydro-7H-thiochromene-6-carbaldehyde 
• 112405-20-6 7-Methyl-2,3-diphenyl-8,8a-dihydro-7H-thiochromene-6-carbaldehyde 
• 112405-19-3 2-(4-Methoxy-phenyl)-7-methyl-8,8a-dihydro-7H-thiochromene-6-carbaldehyde 
• 112405-21-7 2-(4-Dimethylamino-phenyl)-7-methyl-8,8a-dihydro-7H-thiochromene-6-carbaldehyde 
• 112405-22-8 2,3-Bis-(4-methoxy-phenyl)-7-methyl-8,8a-dihydro-7H-thiochromene-6-carbaldehyde 
• 119751-99-4 erythro-4-hydroxy-3-methyl-4-(6-methylcyclohexa-1,3-dienyl)butan-2-one 
• 119751-99-4 threo-4-hydroxy-3-methyl-4-(6-methylcyclohexa-1,3-dienyl)butan-2-one 
• 498-21-5 2-methylbutanedioic acid 
• 95-47-6 o-xylene 
• 108-88-3 toluene 

Relevant academic research and scientific papers

CHEMISTRY OF ENOL ETHERS. LXXXVI. DIENE CONDENSATION OF 2-TRIMETHYLSILYLOXY-1,3-DIENES WITH α,β-UNSATURATED ALDEHYDES. 1-FORMYL-4-TRIMETHYLSILYLOXY-3-CYCLOHEXENES AND 1-FORMYL-4-OXOCYCLOHEXANES

The diene condensation of a series of 2-trimethylsilyloxy-1,3-dienes (2-trimethylsilyloxy-1,3-butadiene, 2-trimethylsilyloxy-1,3-pentadiene, 2-trimethylsilyloxy-4-methyl-1,3-pentadiene) with acrylaldehyde and crotonaldehyde is distinguished by high regioselectivity and low stereoselectivity.The "para" adducts (1-formyl-4-trimethylsilyloxy-3-cyclohexenes) are formed exclusively in all cases, and the reaction leads to the formation of a mixture of the cis and trans isomers with respect to the asymmetric centers.Alcoholysis or acid hydrolysis of 1-formyl-4-trimethylsilyloxy-3-cyclohexenes give high yields of 1-formyl-4-oxocyclohexanes.In a number of cases the diene condensation is accompanied by the formation of undesirable side compounds, produced as a result of transsilylation, which takes place between the 2-trimethylsilyloxy-1,3-diene and crotonaldehyde used in the reaction.

CONDENSATION OF ETHYL AND METHYL 4-(TRIPHENYLPHOSPHORANYLIDENE)-3-OXOBUTANOATE WITH ENALS

The manipulation of the mode of reaction of 4-(phosphoranylidene)-3-oxobutanoates with enals and a resulting new synthesis of ethyl β-safranate have been explored.

CHEMISTRY OF ENOL ETHERS. LXII. DIENE CONDENSATION OF 1-TRIMETHYLSILYLOXY-1,3-DIENES WITH α,β-UNSATURATED ALDEHYDES

The diene condensation of 1-trimethylsilyloxy-1,3-dienes (1-trimethylsilyloxy-1,3-butadiene, 1-trimethylsilyloxy-2-methyl-1,3-pentadiene, 1-trimethylsilyloxy-3-methyl-1,3-butadiene) with α,β-unsaturated aldehydes (acrylic, crotonic) is regioselective, leading to the formation of the "ortho isomers," and the cis-adducts are obtained preferentially.When heated with 10percent hydrochloric acid, the mono- and dimethyl-substituted 1-formyl-2-trimethylsilyloxy-3-cyclohexenes obtained during the diene condensation give high yields of the corresponding substituted 1-formyl-1,3-cyclohexadienes.

ELECTROCHEMICAL HYDROXYSELENENYLATION AS A NEW METHOD FOR ONE-STEP PREPARATION OF α-ARYLSELENO-α,β-UNSATURATED ALDEHYDES FROM 3-HYDROXYALKYNES

Electrochemical oxidation of 3-hydroxyalkynes in the presence of diaryl diselenides in MeCN-H2O provided α-arylseleno-α,β-unsaturated aldehydes 2 in 62-94percent yields via hydroxyselenenylation of alkynes.

Diels-Alder Route to Potential Trichothecene Precursors

2-Methyl-3-yn-2-ol (9) is efficiently converted into 6-formyl-3,6-dimethylcyclohex-2-enyl acetate (4b) and into 6-acetyl-3,6-dimethylcyclohex-2-enyl acetate (4c) via highly regio- and stereo-selective Diels-Alder cycloadditions of 3-methylbuta-1,3-dienyl acetate (2b).The cycloadduct (4b) is converted by base into 4a,5,6,8a-tetrahydro-4a,7-dimethylcoumarin (13b), whilst the cycloadduct (4c) yields 2,3,4a,5,6,8a-hexahydro-2-hydroxy-2,4a,7-trimethylchroman-4-one (15), the structure of which was confirmed by X-ray analysis.Both (13b) and (15) possess a number of structural features of the trichothecenes and may be of value in their total synthesis.

Electronic Energy Levels in a Homologous Series of Unsubstituted Linear Polyenes

Absorption, emission, and exitation spectra of 1,3,5,7-octatetraene, 1,3,5,7,9-decapentaene, and 1,3,5,7,9,11-dodecahexaene have been obtained in room temperature solutions and 77 K glasses.All spectra exibit the chracteristic gap between the origin of the strongly allowed absorption (1Ag --> 1Bu) and the origin of fluorescence (1Ag* --> 1Ag).Comparison with results previously obtained for methyl-substituted polyenes shows that the 1Bu-1Ag* energy gap is a sensitive function of the degree of substitution.Solvent-effects studies have been used to extrapolate transition energies of the unsubstituted polyenes to gas-phase conditions.For the tetraene, pentaene, and hexaene the 1Bu-1Ag* energy differences are 6380, 7050, and 7420 cm-1, respectively.These results are discussed in terms of current theoretical descriptions of polyene electronic states.

Phase-Transfer Catalyzed Reactions. 5. Dramatic Effect of the Concentration of Base on the Dimerization of Crotonaldehyde

Self-condensation of crotonaldehyde under base-catalyzed phase-transfer conditions leads to aldehydes 3 or 4, depending only on the concentration of aqueous hydroxide used.Quaternary ammonium fluorides in anhydrous THF is shown to be a useful system for conjugate additions involving base-sensitive aldehydes.