22442-01-9

Basic information

• Product Name: (2E)-3-methylcyclopentadec-2-en-1-one
• Synonyms: (2E)-3-Methylcyclopentadec-2-en-1-one; 2-cyclopentadecen-1-one, 3-methyl-, (2E)-
• CAS NO: 22442-01-9
• Molecular Formula: C₁₆H₂₈O
• Molecular Weight: 236.3929
• Mol File: 22442-01-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 357.225°C at 760 mmHg
• Flash Point: 158.907°C
• Density: 0.863g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.45
• CAS DataBase Reference: (2E)-3-methylcyclopentadec-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-methylcyclopentadec-2-en-1-one(22442-01-9)
• EPA Substance Registry System: (2E)-3-methylcyclopentadec-2-en-1-one(22442-01-9)

Safety Data

• Hazardous Substances Data: 22442-01-9(Hazardous Substances Data)

Upstream product

• 18650-13-0 hexadecane-2,15-dione 
• 3344-70-5 1,12-dibromododecane 
• 4101-68-2 1,10-dibromodecane 
• 373596-12-4 1,14-diethyl 2,13-diacetyltetradecanedioate 
• 16355-92-3 1,10-diiododecane 
• 434283-08-6 1-Vinyl-cycloundecanol 
• 832-29-1 1-(aminomethyl)cyclododecanol 
• 50361-51-8 1-trimethylsilyloxy-1-cyclododecanecarbonitrile 
• 832-10-0 cyclotridecanone 
• 878-13-7 cycloundecanone 
• 39750-95-3 hexadeca-1,15-diyne 
• 308357-37-1 3-methylene-cyclopentadec-1-yne 
• 434312-80-8 1-prop-1-ynyl-cyclotridecanol 
• 54561-25-0 15,15-Dichloro-1-ethoxy-bicyclo[12.1.0]pentadecane 

Downstream Products

• 956-82-1 3-methylcyclopentadecanone 
• 10403-00-6 (R)-3-methyl-1-cyclopentadecanone 
• 63975-98-4 (S)-muscone 

Relevant articles and documents

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Continuous preparation method of DL-muscone

The invention discloses a continuous preparation method of DL-muscone. The preparation method comprises the following steps: 1) dissolving 2,15-hexadecanedione diketone in an aprotic solvent, then carrying out a continuous reaction in a fixed-bed cyclization reactor for generating a 3-methylcyclopentanone analogue under the action of a cyclization catalyst; 2) carrying out desolvation on the 3-methylcyclopentanone analogue, dissolving the obtained product in a protic solvent, then carrying out a continuous reaction with hydrogen in a fixed-bed hydrogenation reactor under the action of a hydrogenation catalyst to obtain muscone; and 3) carrying out desolvation on the product obtained in the step 2), carrying out continuous chromatographic separation, and carrying out desolvation on the product liquid containing the DL-muscone to obtain the DL-muscone product. The method for preparing the DL-muscone provided by the invention has high process stability and high product yield, continuous production of the DL-muscone can be realized, the production cost is greatly reduced, and the effective capacity of a device is improved.

PROCESS FOR PRODUCTION OF 3-METHYL-CYCLOPENTADECENONE, PROCESS FOR PRODUCTION OF R/S-MUSCONE, AND PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE MUSCONE

By intramolecular condensation reaction of 2,15-hexadecanedione in a gaseous phase with a compound of a Group II element of the Periodic Table as a catalyst, 3-methyl-cyclopentadecenones is generated. Magnesium oxide, calcium oxide, or zinc oxide is desirable as the catalyst for the intramolecular condensation reaction. (R)- and (S)-muscone is generated by subjecting 3-methyl-cyclopentadecenones obtained as above to hydrogenation by using a catalyst. Palladium catalyst is desirable as the hydrogenation catalyst. Optically active muscone is generated by separating 3-methyl-cyclopentadecenones into respective components thereof by means of precision distillation and subsequently subjecting the separated 3-methyl-cyclopentadecenones to asymmetric hydrogenation by using an optically active ruthenium complex catalyst. The production methods described above enable easy and economical production of 3-methyl-cyclopentadecenones, (R)-and (S)-muscone, and optically active muscone.

Enantioselective routes to (-)-(R)-muscone

The macrocyclic ring of muscone was prepared by Pd-catalyzed cyclization of hexadeca-1,15-diyne, which was converted to cyclopentadec-2-enone. The stereogenic center was introduced by enantioselective Cu-catalyzed conjugate addition of dimethylzinc. Because the ee in this step was only moderate, a new route via cyclopentadeca-2,14-dienone was developed. Enantioselective conjugate addition to this substrate led to 14-methylcylodec-2-enone, which was hydrogenated to give (-)-(R)-muscone in high overall yield with up to 98% ee. Georg Thieme Verlag Stuttgart.