100017-18-3

Basic information

• Product Name: (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE
• Synonyms: (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE
• CAS NO: 100017-18-3
• Molecular Formula: C₉H₁₆O₃
• Molecular Weight: 172.22
• Product Categories: Chiral Building Blocks;Lactones;Organic Building Blocks
• Mol File: 100017-18-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 82-84 °C(lit.)
• Boiling Point: 252.9°Cat760mmHg
• Flash Point: 99.7°C
• Appearance: /
• Density: 1.005g/cm³
• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: 1.435
• Storage Temp.: −20°C
• CAS DataBase Reference: (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE(100017-18-3)
• EPA Substance Registry System: (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE(100017-18-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 100017-18-3(Hazardous Substances Data)

Usage

General Description

"(2R,6R)-2-tert-butyl-6-methyl-1,3-dioxan-4-one" is a chemical compound with a molecular formula of C10H18O2. It is a cyclic ketone that is commonly used as a building block in organic synthesis. (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE is known for its ability to undergo a variety of chemical reactions, making it useful in the production of a wide range of different substances. It is also used as a flavoring agent in the food industry, adding a sweet, fruity, and slightly floral aroma and taste to various products. In addition to these applications, (2R,6R)-2-tert-butyl-6-methyl-1,3-dioxan-4-one has potential applications in pharmaceuticals, agrochemicals, and cosmetics due to its versatile reactivity and favorable odor profile.

InChI:InChI=1/C9H16O3/c1-6-5-7(10)12-8(11-6)9(2,3)4/h6,8H,5H2,1-4H3/t6-,8-/m1/s1

Upstream product

• 107289-20-3 (2R)-2-(tert-butyl)-6-methyl-2H,4H-1,3-dioxin-4-one 
• 625-72-9 (R)-3-hydroxybutyric acid 
• 630-19-3 pivalaldehyde 
• 108438-96-6 trimethylsilyl (R)-3-<(trimethylsilyl)oxy>butyrate 

Downstream Products

• 155455-46-2 (1'S,2R,5R,6R)-2-(tert-butyl)-5-(1'-hydroxy-2',2'-diphenylethyl)-6-methyl-1,3-dioxan-4-one 
• 195886-76-1 (2R,5R,6R)-2-tert-Butyl-5-[4-(tert-butyl-diphenyl-silanyloxymethyl)-benzyl]-6-methyl-[1,3]dioxan-4-one 
• 406951-36-8 (1'RS,2R,5R,6R)-5-(α-hydroxy-p-methoxybenzyl)-2-tert-butyl-6-methyl-1,3-dioxan-4-one 
• 129287-53-2 (2R,6R)-2-tert-Butyl-5,6-dimethyl-5-phenylselenyl-1,3-dioxan-4-on 
• 129287-59-8 (2R,4S,6R)-2-tert-Butyl-5-hydroxymethyl-6-methyl-4-(2'-phenylethyl)-1,3-dioxan 
• 118356-58-4 (2R,5S,6R)-2-tert-Butyl-5-[(dimethyl-phenyl-silanyl)-phenyl-methyl]-6-methyl-[1,3]dioxan-4-one 
• 118356-58-4 (2R,5R,6R)-2-tert-Butyl-5-[(dimethyl-phenyl-silanyl)-phenyl-methyl]-6-methyl-[1,3]dioxan-4-one 
• 118356-57-3 (2R,5S,6R)-2-tert-Butyl-5-[(tert-butyl-dimethyl-silanyl)-phenyl-methyl]-6-methyl-[1,3]dioxan-4-one 
• 118356-57-3 (2R,5R,6R)-2-tert-Butyl-5-[(tert-butyl-dimethyl-silanyl)-phenyl-methyl]-6-methyl-[1,3]dioxan-4-one 
• 118375-36-3 (2R,5S,6R)-2-tert-Butyl-6-methyl-5-(phenyl-triethylsilanyl-methyl)-[1,3]dioxan-4-one 
• 118356-56-2 (2R,5S,6R)-2-tert-Butyl-6-methyl-5-(phenyl-trimethylsilanyl-methyl)-[1,3]dioxan-4-one 
• 147673-29-8 (1'R,2R,5S,6R)-5-<1'-benzoyloxy-1'-(naphth-1-yl)methyl>-2-(tert-butyl)-6-methyl-1,3-dioxan-4-one 
• 147673-30-1 (1'S,2R,5S,6R)-5-<1'-benzoyloxy-1'-(naphth-1-yl)methyl>-2-(tert-butyl)-6-methyl-1,3-dioxan-4-one 
• 147673-25-4 (1'R,2R,5S,6R)-5-<1'-benzoyloxy-1'-(naphth-2-yl)methyl>-2-(tert-butyl)-6-methyl-1,3-dioxan-4-one 

Relevant articles and documents

Absolute configurations of melanoxadin, MR-93A, melanoxazal, and MR-93B

Fungal metabolites melanoxadin, MR-93A, melanoxazal, and MR-93B were synthesized with the key stereogenic centers derived from commercially available chiral building blocks. The optically active synthetic products with well-defined absolute configurations provided authentic samples for the stereoisomers of these oxazole-containing natural products and thus allowed for unambiguous assignments of their relative and absolute configurations. The large discrepancies in the optical rotations between the natural and the pure synthetic samples are discussed. Some errors in the previously reported NMR signal assignments are also corrected.

123. 1,3-Dioxanone Derivatives from β-Hydroxy-carboxylic Acids and Pivalaldehyde. Versatile Buiding Blocks for Syntheses of Enantiomerically Pure Compounds. A Chiral Acetoacetic Acid Derivative

(R)-3-Hydroxybutyric acid (from the biopolymer PHB) and pivalaldehyde give the crystalline cis- or (R,R)-2-(tert-butyl)-6-methyl-1,3-dioxan-4-one (1a), the enolate of which is stable at low temperature in THF solution and can be alkylated diastereoselectively (->3, 4, 5, and 7).Phenylselenation and subsequent elimination give an enantiomerically pure enol acetal 10 of aceto-acetic acid.Some reactions of 10 have been carried out, such as Michael addition (->11), alkylation on the CH3 substituent (->13), hydrogenation of the C=C bond (->1a) and photochemical cycloaddition (->16).The overall reactions are substitutions on the one sterogenic center of the starting β-hydroxy acid without racemization and without using a chiral auxiliary.