4423-79-4

Basic information

• Product Name: 2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE
• Synonyms: 2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE;1,4-DIOXASPIRO[4.5]-2-DECANONE;1,4-DIOXASPIRO[4.5]DECAN-2-ONE;2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE 98+%
• CAS NO: 4423-79-4
• Molecular Formula: C₈H₁₂O₃
• Molecular Weight: 156.18
• Product Categories: Dioxanes & Dioxolanes;Dioxolanes;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactones;Organic Building Blocks
• Mol File: 4423-79-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 32-35 °C(lit.)
• Boiling Point: 70 °C0.5 mm Hg(lit.)
• Flash Point: 221 °F
• Appearance: /
• Density: 1.0887 (rough estimate)
• Vapor Pressure: 0.0165mmHg at 25°C
• Refractive Index: 1.4430 (estimate)
• CAS DataBase Reference: 2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE(4423-79-4)
• EPA Substance Registry System: 2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE(4423-79-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 4423-79-4(Hazardous Substances Data)

Usage

Description

2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE, also known as 1,4-Dioxaspiro[4.5]decan-2-one, is an organic compound that serves as an important intermediate in the synthesis of various complex molecules. Its unique structure and properties make it a valuable building block in organic chemistry.
Used in Pharmaceutical Industry:
2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE is used as a key intermediate in the synthesis of L-callipeltose, the deoxyamino sugar of L-callipeltoside A. 2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE has potential applications in the development of new drugs and therapeutic agents, particularly in the field of cancer treatment and drug delivery systems.
Used in Organic Chemistry Research:
2,2-PENTAMETHYLENE-1,3-DIOXOLAN-4-ONE is used as a versatile building block in organic chemistry research for the synthesis of complex organic molecules and natural products. Its unique structure allows for various synthetic transformations, making it a valuable tool for chemists in the development of new compounds and materials.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 1353, 1987 DOI: 10.1021/jo00383a038

InChI:InChI=1/C8H12O3/c9-7-6-10-8(11-7)4-2-1-3-5-8/h1-6H2

Upstream product

• 33581-77-0 trimethylsilyl [(trimethylsilyl)oxy]acetate 
• 108-94-1 cyclohexanone 
• 94034-49-8 5'-bromocyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 344886-78-8 5'-isobutylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 94034-51-2 5'-n-butylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 93831-17-5 (Z)-5'-benzylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 94034-50-1 5'-oxocyclohexanespiro-2'-(1',3'-dioxolan)-4'-yltriphenylphosphonium bromide 
• 93796-39-5 5'-triphenylphosphoranylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 79-14-1 glycolic Acid 
• 7633-32-1 tert-butyl glyoxylate 
• 933-40-4 cycloxexanone dimethyl ketal 

Downstream Products

• 23782-85-6 3-phenyltetronic acid 
• 108-94-1 cyclohexanone 
• 94034-50-1 5'-oxocyclohexanespiro-2'-(1',3'-dioxolan)-4'-yltriphenylphosphonium bromide 
• 94034-54-5 (Z)-5'-(4-benzyloxybenzylidene)cyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 94046-03-4 5'(5-phenylpenta-2,4-dienylidene)cyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 94034-53-4 5'-cinnamylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 94034-68-1 5'-benzylcyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 93831-17-5 (Z)-5'-benzylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 94034-67-0 5'-cyclohexylmethylcyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 93796-39-5 5'-triphenylphosphoranylidenecyclohexanespiro-2'-(1',3'-dioxolan)-4'-one 
• 590-67-0 1-Methylcyclohexanol 
• 29839-61-0 1-oxaspiro[4.5]decan-3-ol 
• 374073-08-2 (4R,5S)-4-[(R)-1-Hydroxy-1-((R)-3-oxo-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester 
• 166117-14-2 2-[1-Phenyl-meth-(Z)-ylidene]-1,4-dioxa-spiro[4.5]decane 

Relevant articles and documents

The first enantioselective synthesis of palinurin

The first enantioselective synthesis of palinurin has been accomplished starting from commercially available furaldehyde and (R)-methyl-3-hydroxy-2- methylpropionate; the key steps of the synthesis include the use of a chiral pyrrolidine to create the chiral tetronic moiety, and Horner-Wadsworth-Emmons, Wittig and Wittig-Horner reactions to construct the alkene units.

Dioxalanones as synthetic intermediates. Part 6. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), 3-Deoxy-D-Arabino-2-Heptulosonic acid (DAH) and 2-Keto-3-Deoxy-D-Gluconic acid (KDG)

Three biosynthetically significant α-keto acids KDO (7), DAH (8) and KDG (9) have been synthesised via 5-ylidene-1,3-dioxalan-4-one intermediates formed by Wittig reactions of protected monosaccharide-derived aldehydes with the Wittig reagent (3).

Dioxolanones as Synthetic Intermediates. Part 1. Synthesis of α-Keto Acids, α-Keto Aldehydes, and α-Ketols

2,2-Pentamethylene-1,3-dioxolan-4-one (10) has been elaborated to provide 5'-ylidene derivatives using a Wittig approach.This apparently novel class of compounds is subject to nucleophilic attack at the 4-position because of strain inherent in the 5-membered ring.Thus alkaline hydrolysis leads to the formation of α-keto acids; hydride reduction of dioxolanones incorporating conjugated aryl substituents using di-isobutylaluminium hydride leads to α-keto-aldehydes; the reaction of dioxolanone (15) with methylmagnesium iodide gave the α-ketol (40).