4748-86-1

Basic information

• Product Name: 6-methylcyclohexa-1,3-diene-1-carbaldehyde
• Synonyms: 6-methylcyclohexa-1,3-diene-1-carbaldehyde;6-Methyl-1,3-cyclohexadiene-1-carbaldehyde;Einecs 225-269-3
• CAS NO: 4748-86-1
• Molecular Formula: C₈H₁₀O
• Molecular Weight: 122.1644
• EINECS: 225-269-3
• Mol File: 4748-86-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 199.6°Cat760mmHg
• Flash Point: 72.4°C
• Appearance: /
• Density: 1.038g/cm³
• Vapor Pressure: 0.339mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: 6-methylcyclohexa-1,3-diene-1-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 6-methylcyclohexa-1,3-diene-1-carbaldehyde(4748-86-1)
• EPA Substance Registry System: 6-methylcyclohexa-1,3-diene-1-carbaldehyde(4748-86-1)

Safety Data

• Hazardous Substances Data: 4748-86-1(Hazardous Substances Data)

Usage

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

Upstream product

• 110-89-4 piperidine 
• 64-19-7 acetic acid 
• 123-73-9 crotonaldehyde 
• 7732-18-5 water 
• 123-73-9 trans-Crotonaldehyde 
• 127-09-3 sodium acetate 
• 78-94-4 methyl vinyl ketone 
• 82454-07-7 1-(4-Chloro-phenylselanyl)-6-methyl-cyclohex-3-enecarbaldehyde 
• 108-24-7 acetic anhydride 
• 98815-59-9 (3-methoxycarbonyl-2-oxopropylidene)triphenylphosphorane 
• 6651-43-0 1-(trimethylsiloxy)-1,3-butadiene 
• 38053-91-7 2-trimethylsilyloxy-1,3-butadiene 
• 1515-76-0 1-acetoxy-1,3-butadiene 
• 109-89-7 diethylamine 

Downstream Products

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

Relevant articles and documents

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.

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.

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.