4316-49-8

Basic information

• Product Name: 7-Methyl-1,6-dioxaspiro[4.4]nonane-2-acetic acid
• Synonyms: 7-Methyl-1,6-dioxaspiro[4.4]nonane-2-acetic acid;Exogonic acid
• CAS NO: 4316-49-8
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23
• Mol File: 4316-49-8.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Methyl-1,6-dioxaspiro[4.4]nonane-2-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Methyl-1,6-dioxaspiro[4.4]nonane-2-acetic acid(4316-49-8)
• EPA Substance Registry System: 7-Methyl-1,6-dioxaspiro[4.4]nonane-2-acetic acid(4316-49-8)

Safety Data

• Hazardous Substances Data: 4316-49-8(Hazardous Substances Data)

Upstream product

• 119681-13-9 exogonal 
• 3620-18-6 3-acetyl-5-methyldihydrofuran-2(3H)-one 
• 91006-92-7 (2R,5RS,7S)-2-(2'-Hydroxyethyl)-7-methyl-1,6-dioxaspiro<4.4>nonane 
• 137846-91-4 tert-Butyl-dimethyl-[2-((2S,5S,7R)-7-methyl-1,6-dioxa-spiro[4.4]non-2-yl)-ethoxy]-silane 
• 119681-12-8 2-Methyl-7-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1,6-dioxa-spiro[4.4]nonane 
• 60551-20-4 γ-(carboxymethyl)-γ-butyrolactone 
• 119681-13-9 (2R,5RS,7S)-Exogonal 
• 119681-11-7 2-(4'-hydroxy-1'-oxo-6'-tetrahydropyranyloxy)-4-pentanolide 
• 91006-92-7 racemic Exogonol 

Downstream Products

• 20969-25-9 racemic Methyl exogonate 
• 627-93-0 hexanedioic acid dimethyl ester 

Relevant articles and documents

Synthesis of Exogonic Acid and Related Compounds

Hydroxymercuration, cyclization, and reduction of appropriate hydroxy ketones or enones carrying a suitably located α,β-unsaturated ester function is an efficient route to exogonic acid (2-(carboxymethyl)-7-methyl-1,6-dioxaspirononane), a resin constituent of the Brazilian tree Ipomoea operculata (Martin), and related and spiroketal systems.Procedures incorporating stereocontrol at C-2 and C-7 of exogonic acid are also reported and involve sequential alkylation with epoxypropane and 1,2-epoxy-4-(tetrahydropyranyloxy)butane of anions (or dianions) derived from methyl acetoacetate or acetone dimethylhydrazone.

Naturally Occurring Spirocyclic Ketals from Lactones. 3

Our earlier methodology for the synthesis of 1,6-dioxaspirononane and 1,6-dioxaspirodecane derivatives has been applied to the synthesis of substances found in the mandibular gland secretions of Andrena bees.Use of optically active propylene oxide as a precursor gave 7-methyl-1,6-dioxaspirodecane, reported from Andrena and Vespula species, in 80percent optical purity as shown by 13C NMR spectroscopy with a chiral shift reagent.Adaptations of the method allowed synthesis of a tetramethyl-1,6-dioxaspirononene found in Japanese hop oil and of exogonic acid, a resin constituent of the Brazilian tree Ipomoae operculata (Martin).We have also simplified our synthesis of chalcogran, 2-ethyl-1,6-dioxaspirononane, by using γ-caprolactone and the lithium reagent prepared from 3-bromo-1-propyl 1-ethoxyethyl ether.