3-Methylcyclopentadecanone

Base Information

• Chemical Name: 3-Methylcyclopentadecanone
• CAS No.: 541-91-3
• Deprecated CAS: 22460-48-6,956-82-1,956-82-1
• Molecular Formula: C16H30O
• Molecular Weight: 238.41
• Hs Code.: 2914700090
• European Community (EC) Number: 208-795-8
• UNII: 5JO79R7S9R
• DSSTox Substance ID: DTXSID8052192
• Nikkaji Number: J6.397E
• Wikipedia: Muscone
• Wikidata: Q416022
• Metabolomics Workbench ID: 46406
• Mol file: 541-91-3.mol

Synonyms:3-methylcyclopentadecanone;DL-3-methylcyclopentadecanone;muscone;muscone, (+-)-;muskone

Chemical Property of 3-Methylcyclopentadecanone

Chemical Property:

• Appearance/Colour: white to yellowish semi-solid
• Vapor Pressure: 0.000176mmHg at 25°C
• Melting Point: 33oC
• Refractive Index: 1.436
• Boiling Point: 329.5 °C at 760 mmHg
• Flash Point: 145.3 °C
• PSA: 17.07000
• Density: 0.843 g/cm³
• LogP: 5.27650
• Storage Temp.: -20°C
• Solubility.: Chloroform, Methanol (Sparingly)
• Water Solubility.: 430μg/L at 20℃
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 238.229665576
• Heavy Atom Count: 17
• Complexity: 198

Purity/Quality:

≥98% ^*data from raw suppliers

MUSK ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: CC1CCCCCCCCCCCCC(=O)C1
• General Description: Muscone, also known as Moschus ketone or Muskone, is a macrocyclic ketone with a musky odor, commonly used in perfumery. The synthesis of racemic muscone (rac-Muscone) involves ring expansion techniques, starting from intermediates like 1-morpholino-cyclododec-1-ene, followed by reactions with ketene, saponification, decarboxylation, and hydrogenation to yield the final product. This process highlights Muscone's structural complexity and the utility of ring expansion methods in its preparation.

Refernces

Application of ring expansions for the preparation of rac muscone and exaltone

10.1002/hlca.19750580821

The research focuses on the synthesis of complex organic compounds, specifically the preparation of rac-Muscone and Exaltone using ring expansions. Key chemicals involved include 1-morpholino-cyclododec-1-ene (7) and 1-morpholino-cyclotridec-1-en (15), which were reacted with ketene to form 4,6-Undecamethylene-2-pyron (8) and 4,6-Dodecamethylene-2-pyron (16), respectively. These compounds were then subjected to saponification and decarboxylation processes to produce mixtures of 3-methyl-cycloalkenones, which were subsequently hydrogenated to yield the desired products. The study also explores the application of the keton homologation method of Mock & Hartman, using diazoacetic ester and triethyl oxonium fluoroborate to synthesize higher homologs of cyclododecanone (1), resulting in cyclotridecanone (4) and cyclopentadecanone (5). Additionally, the research investigates the radical anion of 2,7-diazapyrene and its protonated forms, examining the changes in coupling constants and orbital sequences upon protonation.