53263-58-4

Basic information

• Product Name: 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one
• Synonyms: 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one;2-Cyclopenten-1-one, 5-ethyl-2-hydroxy-3-methyl-;5-ETHYL-2-HYDROXY-3-METHYL-2-CYCLOPENTEN-1-ON;5-ETHYL-3-METHYL CYCLOTENE;5-Ethyl-2-hydroxy-3-methylcycolpent-2-en-1-one;5-Ethyl-2-hydroxy-3-methyl-2-cyclopenten-1-one;Ethylcyclotene;YGSOVVMFKDBTKX-UHFFFAOYSA-N
• CAS NO: 53263-58-4
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.17968
• EINECS: 258-451-6
• Mol File: 53263-58-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 260.5 °C at 760 mmHg
• Flash Point: 108 °C
• Appearance: /
• Density: 1.086g/cm³
• Vapor Pressure: 0.00177mmHg at 25°C
• Refractive Index: 1.507
• PKA: 9.22±0.40(Predicted)
• CAS DataBase Reference: 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one(53263-58-4)
• EPA Substance Registry System: 5-ethyl-2-hydroxy-3-methylcyclopent-2-en-1-one(53263-58-4)

Safety Data

• Hazardous Substances Data: 53263-58-4(Hazardous Substances Data)

Usage

Occurrence

Reported found in coffee.

InChI:InChI=1/C8H12O2/c1-3-6-4-5(2)7(9)8(6)10/h6,9H,3-4H2,1-2H3

Upstream product

• 504-29-0 2-aminopyridine 
• 74-85-1 ethene 
• 765-70-8 3-methyl-1,2-cyclopentanedione 
• 1394172-84-9 C₁₃H₁₆N₂O 
• 1394172-79-2 5-methyl-2-(pyridin-2-ylamino)cyclopent-2-enone 
• 127663-18-7 5-ethyl-2-methoxy-3-methyl-2-cyclopenten-1-one 

Relevant articles and documents

Catalytic intermolecular C-alkylation of 1,2-diketones with simple olefins: A recyclable directing group strategy

We describe the first example of Rh-catalyzed intermolecular C-alkylation of cyclic 1,2-diketones using simple terminal olefins as alkylating agents. Aminopyridine is employed as a recyclable directing group. First, it reacts with ketones to give enamines and delivers Rh to activate the vinyl C-H bonds in the same pot; second, it can be cleaved off and recovered via hydrolysis. A broad range of olefins can be utilized as substrates, including aliphatic, aromatic olefins and vinyl esters. The efficiency of this method is also demonstrated in the synthesis of a natural flavoring compound, 3-ethyl-5-methyl-1,2- cyclopentadione (one-pot 53% yield vs a previous four-step route 16% yield from the same starting material). This work is expected to serve as a seminal study toward catalytic ketone α-alkylation with unactivated olefins.