3-Hydroxy-2-methyl-cyclopent-2-enone

Base Information

• Chemical Name: 3-Hydroxy-2-methyl-cyclopent-2-enone
• CAS No.: 5870-63-3
• Molecular Formula: C6H8 O2
• Molecular Weight: 112.128
• DSSTox Substance ID: DTXSID70207403
• Nikkaji Number: J853.317B
• Wikidata: Q83081306
• ChEMBL ID: CHEMBL1829795
• Mol file: 5870-63-3.mol

Synonyms:5870-63-3;3-Hydroxy-2-methyl-cyclopent-2-enone;3-Hydroxy-2-methyl-2-cyclopenten-1-one;2-Cyclopenten-1-one,3-hydroxy-2-methyl-;2-Cyclopenten-1-one, 3-hydroxy-2-methyl-;3-hydroxy-2-methylcyclopent-2-en-1-one;3-hydroxy-2-methylcyclopent-2-enone;SCHEMBL123412;CHEMBL1829795;DTXSID70207403;AKOS006291341;2-Methyl-3-hydroxy-2-cyclopenten-1-one;3-Hydroxy-2-methyl-2-cyclopenten-1-one #;TRANS,TRANS-4-(3,4-DIFLUOROPHENYL)-4-BUTYL-BICYCLOHEXYL

Chemical Property of 3-Hydroxy-2-methyl-cyclopent-2-enone

Chemical Property:

• Melting Point: 213-215 °C(Solv: ethanol (64-17-5))
• Boiling Point: 212.2°Cat760mmHg
• PKA: 4.82±0.30(Predicted)
• Flash Point: 84.4°C
• PSA: 37.30000
• Density: 1.225g/cm³
• LogP: 1.18130
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 156

Purity/Quality:

99%, ^*data from raw suppliers

3-hydroxy-2-methylcyclopent-2-enone 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(CCC1=O)O

Technology Process of 3-Hydroxy-2-methyl-cyclopent-2-enone

There total 7 articles about 3-Hydroxy-2-methyl-cyclopent-2-enone 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: 71.0%

2-methylcyclopentane-1,3-dione ethylene glycol monoacetal (54972-03-1) → 3-hydroxy-2-methyl-2-cyclopenten-1-one (5870-63-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; for 10h;

DOI:10.1039/c5ob02402a

Reference yield:

cyclopent-2-enone (930-30-3) → 3-hydroxy-2-methyl-2-cyclopenten-1-one (5870-63-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium / diethyl ether / 0.5 h / 0 °C / Inert atmosphere

1.2: 1 h / -78 °C / Inert atmosphere

1.3: 3 h / -78 - 20 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / benzene / 6 h / Reflux; Dean-Stark

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Inert atmosphere

3.2: 20 h

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere

5.1: hydrogenchloride / tetrahydrofuran; water / 10 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; methyllithium; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; benzene; 3.2: |Tamao-Kumada Oxidation;

DOI:10.1039/c5ob02402a

Reference yield:

trans-2-methyl-3-(pentamethyldisilan-1-yl)cyclopentan-1-one → 3-hydroxy-2-methyl-2-cyclopenten-1-one (5870-63-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / benzene / 6 h / Reflux; Dean-Stark

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / Inert atmosphere

2.2: 20 h

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / Molecular sieve; Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; water / 10 h

With hydrogenchloride; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; benzene; 2.2: |Tamao-Kumada Oxidation;

DOI:10.1039/c5ob02402a

upstream raw materials:

cyclopent-2-enone

2-methylcyclopentane-1,3-dione ethylene glycol monoacetal

Downstream raw materials:

2-methyl-2-cyclopenten-1-one-3-carboxylic acid

methyl 2-methyl-3-oxocyclopent-1-ene-1-carboxylate

(S)-Halos-Parish ketone

(+)-(3aS,7aS)-2,3,3a,4,7,7a-hexahydro-3a-hydroxy-7a-methyl-1H-indene-1,5(6H)-dione

Refernces

• 1、 Gao, Fuye,Burnell, D. Jean. "Reactions of 1,2-bis(trimethylsilyloxy)cycloalkenes with the diethyl acetals of aldehydes". . p. 356 - 359. Retrieved 2007/10/03.