160389-86-6

Basic information

• Product Name: (12R)-(-)-12-methyl-10-oxo-13-tridecanolide
• CAS NO: 160389-86-6
• Molecular Weight: 240.343
• Mol File: 160389-86-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (12R)-(-)-12-methyl-10-oxo-13-tridecanolide(CAS DataBase Reference)
• NIST Chemistry Reference: (12R)-(-)-12-methyl-10-oxo-13-tridecanolide(160389-86-6)
• EPA Substance Registry System: (12R)-(-)-12-methyl-10-oxo-13-tridecanolide(160389-86-6)

Safety Data

• Hazardous Substances Data: 160389-86-6(Hazardous Substances Data)

Upstream product

• 1502-06-3 cyclodecanone 
• 160389-85-5 (13R)-(-)-13-methyl-11-oxabicyclo<8.4.0>-tetradec-1(10)-ene 

Relevant articles and documents

Synthesis of Medium and Large Ring Compounds, XXXVIII. - Ring Enlargement of Cyclodecanone by a Chiral Building Block: Synthesis and Olfactory Properties of (12R)-(+)-12-Methyl-13-tridecanolide

The title compound (+)-3 was synthesized in four steps by ring enlargement of cyclodecanone (6) with the chiral building block 5.The protected hydroxy halide 5, easily prepared from commercially available (2S)-(+)-methyl 3-hydroxy-2-methylpropanoate (4), was introduced by HMPA-mediated enolate alkylation and subsequent formation of the cyclic enol ether 8.Ozonolysis and mild chemoselective reduction of the carbonyl function led to the optically active target molecule (+)-3, which possesses a very interesting clear musk note with elegant sandalwood aspects. - Key Words: Angelica root oil / Ring enlargement / Chiral building block / Olfactory properties / Propanoic acid, 3-hydroxy-2-methyl, methyl ester / Oxacyclotetradecan-2-one, 13-methyl-