3-Methyl-1-phenylcyclopent-1-ene

Base Information

• Chemical Name: 3-Methyl-1-phenylcyclopent-1-ene
• CAS No.: 57497-04-8
• Molecular Formula: C₁₂H₁₄
• Molecular Weight: 158.243
• Mol file: 57497-04-8.mol

Synonyms:3-Methyl-1-phenylcyclopent-1-ene

Chemical Property of 3-Methyl-1-phenylcyclopent-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of 3-Methyl-1-phenylcyclopent-1-ene

There total 7 articles about 3-Methyl-1-phenylcyclopent-1-ene 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: 28.0%

bromobenzene (108-86-1,52753-63-6) + 3-Methylcyclopentenyl triflate (98056-45-2) → 3-Methyl-1-phenylcyclopent-1-ene (57497-04-8)

Guidance literature:

With lithium; copper(I) bromide; In diethyl ether; for 8h; Ambient temperature;

DOI:10.1021/jo00109a043

Reference yield:

(1R,2S,5S)-2-Phenyl-bicyclo[3.1.0]hexane-2-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester → 1-Phenylcyclohexene (771-98-2) + 3-Methyl-1-phenylcyclopent-1-ene (57497-04-8) + 1-Phenylbicyclo[3.1.0]hexane

Guidance literature:

With 2-methylpropan-2-thiol; In benzene; at -0.1 ℃; Rate constant; Product distribution; Thermodynamic data; Irradiation; other temp., various conc. of t-BuSH; ΔΔH(excit.), ΔΔS(excit.), ΔΔG(excit.) for exocyclic ring scission vs. endocyclic ring opening;

DOI:10.1021/jo00109a043

Reference yield:

2-Phenyl-bicyclo[3.1.0]hexane-2-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester (156006-03-0) → 1-Phenylcyclohexene (771-98-2) + 3-Methyl-1-phenylcyclopent-1-ene (57497-04-8) + 1-Phenylbicyclo[3.1.0]hexane

Guidance literature:

With 2-methylpropan-2-thiol; In benzene; for 0.25h; Product distribution; Rate constant; Irradiation; ratio of produkt and ratio of velocity constants;

DOI:10.1021/jo00092a003

upstream raw materials:

1-Brom-2-methyl-5-phenyl-1-penten

2-Phenyl-bicyclo[3.1.0]hexane-2-carboxylic acid 2-thioxo-2H-pyridin-1-yl ester

bromobenzene

3-Methylcyclopentenyl triflate

Refernces

Benzylic Stabilization as a Mechanistic Tool for Studying Radical Rearrangements

10.1021/jo00109a043

The research focused on studying the kinetic parameters and relative energies of radicals involved in the rearrangement of a bicyclic cyclopropylmethylhomoallyl system. The purpose was to understand the effects of benzylic stabilization on the cyclopropylmethyl radical, which facilitates the characterization of all four ring-opening and closing processes. The study concluded that benzylic stabilization does not significantly perturb the position of the transition state for ring opening, suggesting that phenyl substitution of a bicyclic cyclopropylmethyl radical can be a useful tool for analyzing the effects of substituents elsewhere in the system. Key chemicals used in the process included bicyclo[3.1.0]hexan-1-yl, Bu3SnH, PhSH, and t-BuSH as radical traps, as well as a series of synthesized compounds such as 1-phenylbicyclo[3.1.0]hexane, 3-methyl-1-phenylcyclopent-1-ene, and 1-phenylcyclohexene. The research provided insights into the regioselectivity of ring opening and the energetics of isomeric homoallyl radicals, which are valuable for the rational application of cyclopropylmethyl radical rearrangements in organic synthesis.