25183-76-0

Basic information

• Product Name: 1-cyclopentylprop-2-en-1-one
• CAS NO: 25183-76-0
• Molecular Formula: C₈H₁₂O
• Molecular Weight: 124.1803
• Mol File: 25183-76-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 190.6°C at 760 mmHg
• Flash Point: 66.4°C
• Density: 0.943g/cm³
• Vapor Pressure: 0.538mmHg at 25°C
• Refractive Index: 1.468
• CAS DataBase Reference: 1-cyclopentylprop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-cyclopentylprop-2-en-1-one(25183-76-0)
• EPA Substance Registry System: 1-cyclopentylprop-2-en-1-one(25183-76-0)

Safety Data

• Hazardous Substances Data: 25183-76-0(Hazardous Substances Data)

Usage

Physical State

Colorless liquid.

Odor

Sharp, sweet, and floral.

Common Uses

Flavor and fragrance ingredient in perfumes and cosmetics; intermediate in the synthesis of other organic compounds.

Health Hazards

Skin and eye irritant; toxic if ingested or inhaled in large amounts.

Upstream product

• 814-68-6 acryloyl chloride 

Downstream Products

• 872834-99-6 1-cyclopentyl-4-(2-iodophenyl)-1-butanone 
• 872835-00-2 1-(4-cyclopentyl-4-penten-1-yl)-2-iodobenzene 
• 1338441-78-3 2-cyclopentyl-6-phenyl-4-(p-tolyl)pyridine 
• 1338441-55-6 (E)-N-(5-cyclopentyl-5-oxo-1-phenylpent-3-en-1-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Dissociated nonsteroidal glucocorticoid receptor modulators; discovery of the agonist trigger in a tetrahydronaphthalene-benzoxazine series

The tetrahydronaphthalene-benzoxazine glucocorticoid receptor (GR) partial agonist 4b was optimized to produce potent full agonists of GR. Aromatic ring substitution of the tetrahydronaphthalene leads to weak GR antagonists. Discovery of an "agonist trigger" substituent on the saturated ring of the tetrahydronaphthalene leads to increased potency and efficacious GR agonism. These compounds are efficacy selective in an NFkB GR agonist assay (representing transrepression effects) over an MMTV GR agonist assay (representing transactivation effects). 52 and 60 have NFkB pIC50 = 8.92 (105%) and 8.69 (92%) and MMTV pEC50 = 8.20 (47%) and 7.75 (39%), respectively. The impact of the trigger substituent on agonism is modeled within GR and discussed. 36, 52, and 60 have anti-inflammatory activity in a mouse model of inflammation after topical dosing with 52 and 60, having an effect similar to that of dexamethasone. The original lead was discovered by a manual agreement docking method, and automation of this method is also described.

Aluminum chloride (AlCl3) promotes selective oxidative deprotection of benzylic trimethylsilyl and tert-butyldimethylsilyl ethers to the corresponding carbonyl compounds with manganese dioxide (MnO2)

Various types of trimethylsilyl and tert-butyldimethylsilyl ethers of primary and secondary benzylic alcohols could be selectively converted to their corresponding carbonyl compounds with MnO2 in the presence of AlCl3 in good to excellent yields.