19870-49-6

Basic information

• Product Name: 3,9-Undecadien-2-one, 6,10-dimethyl-, (E)-
• CAS NO: 19870-49-6
• Molecular Formula: C13H22O
• Molecular Weight: 194.317
• Mol File: 19870-49-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3,9-Undecadien-2-one, 6,10-dimethyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,9-Undecadien-2-one, 6,10-dimethyl-, (E)-(19870-49-6)
• EPA Substance Registry System: 3,9-Undecadien-2-one, 6,10-dimethyl-, (E)-(19870-49-6)

Safety Data

• Hazardous Substances Data: 19870-49-6(Hazardous Substances Data)

Upstream product

• 106-23-0 3,7-dimethyl-oct-6-enal 
• 67-64-1 acetone 
• 1235-21-8 acetonyltriphenylphosphonium chloride 
• 90660-54-1 6,10-dimethylundeca-1,9-dien-4-ol 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 108-22-5 Isopropenyl acetate 
• 33027-94-0 4-hydroxy-6,10-dimethylundec-9-en-2-one 

Downstream Products

• 36557-27-4 S-(+)-11-methoxy-3,7,11-trimethyldodecadienoic acid isopropyl ester 

Relevant articles and documents

Synthesis of S-(+)-methoprene

An optically active juvenile hormone analogue, S-(+)-methoprene (1), is synthesized in six steps from technical grade S-(+)-3,7-dimethyl-1,6-octadiene (''(+)-dihydromyrcene'', e.e. ca. 50percent) by a novel procedure which begins with selective hydroalumination-oxidation to give S-(-)-citronellol.This alcohol is oxidized to give S-(-)-citronellal which on reaction with allylmagnesium chloride affords 6S,10-dimethyl-1,9-undecadien-4R/S-ol (5).Smidt-Moiseev oxygenation of 5 followed by dehydration leads to 6S,10-dimethyl-3E,9-undecadien-2-one.The latter on treatment with isopropoxyethynylmagnesium bromide is transformed into isopropyl 3,7S,11-trimethyl-2E/Z,4E,10-dodecatrienoate which upon Brown solvomercuration-reduction in MeOH gives 1 in 14percent overall yield.

Selective Synthesis of Unsymmetrical Aliphatic Acyloins through Oxidation of Iridium Enolates

The first method to access unsymmetrical aliphatic acyloins is presented. The method relies on a fast 1,3-hydride shift mediated by an IrIII complex in allylic alcohols followed by oxidation with TEMPO+. The direct conversion of allylic alcohols into acyloins is achieved in a one-pot procedure. Further functionalization of the Cα′ of the α-amino-oxylated ketone products gives access to highly functionalized unsymmetrical aliphatic ketones, which further highlights the utility of this transformation.

Photochemical transformations of terpenoids in the presence of cyclodextrins

The effect of complexation of terpene compounds with cyclodextrins on photolysis depends on the type of cyclodextrin and on the structure of the initial substrates. In some cases, only a change in the reaction rate is observed; in other cases, the complexation results in allylic rearrangements, hydride and acyl shifts, and cyclization with the formation of four-, five-, and six-membered cycles, whereas only cis-trans isomerization reactions are observed in the absence of complexation.