1-METHYL-1-CYCLOHEXENE

Base Information

• Chemical Name: 1-METHYL-1-CYCLOHEXENE
• CAS No.: 591-49-1
• Molecular Formula: C7H12
• Molecular Weight: 96.1723
• Hs Code.: 29021900
• European Community (EC) Number: 209-718-0,215-640-8
• NSC Number: 66539
• UNII: TE4P8Q2044
• DSSTox Substance ID: DTXSID3060451
• Nikkaji Number: J96.131K
• Wikipedia: Methylcyclohexene
• Wikidata: Q63392428
• Mol file: 591-49-1.mol

Synonyms:1-Methylcyclohexene;2-Methylcyclohexene;NSC 66539;a-Methylcyclohexene;

Chemical Property of 1-METHYL-1-CYCLOHEXENE

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 27.4 at 20.2 °C, 36.4 at 25.0 °C (transpiration method, Verevkin et al., 2000)
• Melting Point: -119.4°C
• Refractive Index: n20/D 1.45(lit.)
• Boiling Point: 108.938 °C at 760 mmHg
• Flash Point: 25 °F
• PSA: 0.00000
• Density: 0.817 g/cm³
• LogP: 2.50670
• Storage Temp.: Flammables area
• Solubility.: Soluble in benzene and ether (Weast, 1986) and miscible with many hydrocarbons similar in chemical structure, e.g., cyclohexane, cyclohexene, etc.
• Water Solubility.: 52 mg/kg at 25 °C (shake flask-GC, McAuliffe, 1966)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 96.093900383
• Heavy Atom Count: 7
• Complexity: 80

Purity/Quality:

99%, ^*data from raw suppliers

1-?Methyl-?cyclohexene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xn, Xi
• Hazard Codes: F,Xn,Xi
• Statements: 11-36/37/38-65
• Safety Statements: 16-26-36-62

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: CC1=CCCCC1
• General Description: 1-Methyl-1-cyclohexene is a cycloalkene that exhibits reduced stability in olefin-silver ion complexes due to steric hindrance from its methyl substituent at the double bond. In reactions such as acylation-cycloalkylation with phenylacetyl chloride, it forms both cis- and trans-methylhydrophenanthrones, demonstrating its reactivity and the influence of substituents on product stereochemistry. 1-METHYL-1-CYCLOHEXENE's behavior in complexation and chemical transformations highlights the interplay of steric and electronic effects in its reactivity.

Technology Process of 1-METHYL-1-CYCLOHEXENE

There total 229 articles about 1-METHYL-1-CYCLOHEXENE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C10H19NO2 (865241-08-3) + phenylmagnesium bromide (100-58-3) → 1-methylcyclohex-1-ene (591-49-1) + benzaldehyde (100-52-7)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 2 h / Reflux

2: acetonitrile / Irradiation

In tetrahydrofuran; acetonitrile;

DOI:10.1039/c0cc05337f

Reference yield:

(1-methylcyclohexyl)(phenyl)methanone (2892-99-1) → 1-methylcyclohex-1-ene (591-49-1) + cyclobutanol (2919-23-5) + benzaldehyde (100-52-7)

Guidance literature:

In acetonitrile; Irradiation;

DOI:10.1039/c0cc05337f

Reference yield:

2,7,7-trimethyltricyclo[4.1.1.02,4]octane (286-08-8) + acetic acid (64-19-7,77671-22-8) → 1-methylcyclohex-1-ene (591-49-1) + 3-methyl-1-cyclohexene (591-48-0) + Cycloheptene (628-92-2,45509-99-7) + 1-acetoxy-1-methyl-cyclohexane (16737-30-7) + cycloheptyl acetate (18631-70-4) + (+/-)-trans-2-methylcyclohexanol acetate (5726-19-2,15288-14-9,15288-15-0,20993-78-6,50539-18-9,50539-19-0,54714-33-9,54714-34-0)

Guidance literature:

toluene-4-sulfonic acid; Rate constant; Product distribution; Thermodynamic data; ΔH^(excit.), ΔS^(excit.);

DOI:10.1021/ja00290a042

upstream raw materials:

quinoline

cyclohexylmethyl iodide

phthalic anhydride

1-Methylcyclohexanol

Downstream raw materials:

1-Methyl-1-methoxycyclohexane

2-methyl-2-cyclohexen-1-one

3-methylcyclohexen-2-one

3-methylcyclohex-2-en-1-ol

Refernces

DETERMINATION OF THE STABILITY CONSTANTS OF COMPLEXES BY GAS CHROMATOGRAPHY

10.1021/j100812a519

The study investigates the stability constants of olefin-silver ion complexes in ethylene glycol solutions using gas chromatography. Olefins coordinate with silver ions to form complexes, and the stability of these complexes is influenced by factors such as the position and size of substituents on the olefins. For instance, a methyl substituent at the double bond reduces complex stability due to steric effects, while electronic factors play a role in the higher complex formation tendency of certain 3-alkylcyclopentenes compared to 4-alkyl isomers. The study also finds that cyclopentenes have a higher affinity for silver ions than corresponding cyclohexenes. The stability constants for various olefins, including 1-methylcyclohexene, 3-methylcyclohexene, 4-methylcyclohexene, methylenecyclohexane, and others, are determined and compared, providing insights into the effects of molecular structure on complex stability.

Acylation-Cycloalkylation. Reaction of Phenylacetyl Chloride with Cyclohexene

10.1021/jo01323a029

The study investigates the acylation-cycloalkylation reaction of phenylacetyl chloride with cyclohexene, focusing on the formation of cyclic ketones. The aluminum chloride complex of phenylacetyl chloride reacts with cyclohexene to produce cis-hexahydro-9-phenanthrone (3) along with other products like chloro and unsaturated ketones. The reaction's stereoselectivity and the stability of the products under various conditions are explored. The study also examines the reaction with 1-methylcyclohexene, yielding cis- and trans-methylhydrophenanthrones (30 and 31). The stereochemistry of the ketones is established through conversions to known compounds. The stability of cis-hydrophenanthrone (3) is notable, as it resists isomerization under Friedel-Crafts reaction conditions but readily converts to the trans isomer (2) in the presence of acid, base, or heat. The study provides insights into the reaction mechanism and the factors influencing the selectivity and stability of the products.

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