67884-60-0

Basic information

• Product Name: (Z)-4-Methyl-8-oxo-4-nonenoic acid methyl ester
• Synonyms: (Z)-4-Methyl-8-oxo-4-nonenoic acid methyl ester
• CAS NO: 67884-60-0
• Molecular Formula: C11H18O3
• Molecular Weight: 198.26
• Mol File: 67884-60-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-4-Methyl-8-oxo-4-nonenoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-Methyl-8-oxo-4-nonenoic acid methyl ester(67884-60-0)
• EPA Substance Registry System: (Z)-4-Methyl-8-oxo-4-nonenoic acid methyl ester(67884-60-0)

Safety Data

• Hazardous Substances Data: 67884-60-0(Hazardous Substances Data)

Upstream product

• 124-41-4 sodium methylate 
• 33462-81-6 cyclopropyldiphenylsulfonium tetrafluoroborate 
• 105-45-3 acetoacetic acid methyl ester 
• 186581-53-3 diazomethane 
• 82342-31-2 4-methyl-8-oxo-4Z-nonenoic acid 
• 74866-58-3 2-((E)-2-Methyl-6-oxo-hept-2-enyl)-malonic acid dimethyl ester 
• 82736-45-6 Methyl 2,7-Dicarbomethoxy-4-methyl-8-oxo-4-nonenoate 
• 63284-77-5 (Z)-4-methyl-8-oxo-non-4-enal 
• 73022-52-3 1,5-dimethyl-1,5-cyclooctadiene 
• 67-56-1 methanol 

Relevant articles and documents

Terpenoid Synthesis via Palladium-Catalyzed Allylic Alkylation of Allylic Nitro Compounds

Dimethyl (E,E)-3,7-dimethyl-2,6-decadienedioate and (E)-6,10-dimethyl-9-methylene-5-undecen-2-one (two natural products) are prepared starting from 2-methyl-3-nitropropene/2-methyl-1-nitropropene and butenone by convenient four- and five-step procedures, respectively.

Synthesis of the Major Pheromonal Component of the Monarch Butterfly (Danaus plexippus) via Palladium-Catalyzed 1,4-Functionalization of Isoprene

4-Chloroprenyl acetate (2), regioselectively prepared by palladium(II)-catalyzed 1,4-acetoxychlorination of isoprene, was selectively functionalized in the 1- and 4-positions to afford 6, which is readily transformed to the dimethyl ester of the pheromone (E,E)-3,7-dimethyldeca-2,6-diene-1,10-dioic acid (1a) of the Monarch butterfly.The allylic chloro group in 2 was chemoselectively substituted with sodium dimethyl malonate (classically or with palladium(0) catalysis) without affecting the allylic acetoxy group, which subsequently was replaced with sodium methyl acetoacetate using palladium(0) catalysis to give 5.The configuration of the double bond in 5 is >95percent E when triphenylphosphine is used as ligand.A double alkylation of 2 to 5 can also be performed as a one-pot sequence.Selective double decarboxylation of 5 gave methyl (E)-4-methyl-8-oxo-4-nonenoate (6) in 35 percent overall yield from isoprene.Transformation of 6 to the dimethyl ester of 1 has been described elsewhere.