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

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

Uses

Used in Organic Synthesis:
(2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE is used as a building block in organic synthesis for its capacity to undergo various chemical reactions, facilitating the production of a broad spectrum of substances.
Used in the Food Industry:
In the food industry, (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE is used as a flavoring agent to impart a sweet, fruity, and slightly floral aroma and taste to a variety of products, enhancing their sensory appeal.
Used in Pharmaceutical Applications:
(2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE is utilized in pharmaceuticals due to its potential to be incorporated into the development of new drugs, leveraging its versatile reactivity and chemical properties.
Used in Agrochemical Applications:
In agrochemicals, (2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE is employed for its potential role in the creation of new agrochemical products, possibly contributing to pest control or crop enhancement through its chemical interactions.
Used in Cosmetic Applications:
(2R,6R)-2-TERT-BUTYL-6-METHYL-1,3-DIOXAN-4-ONE is used in cosmetics for its favorable odor profile and potential incorporation into fragrances or other cosmetic formulations, adding to the sensory experience of cosmetic products.

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

• 155455-48-4 (1'R,2R,5R,6R)-2-(tert-butyl)-5-(1'-hydroxy-3'-phenylprop-2'-ynyl)-6-methyl-1,3-dioxan-4-one 
• 129287-51-0 (2R,5R,6R)-2-tert-Butyl-5-[(S)-hydroxy-(4-trifluoromethyl-phenyl)-methyl]-6-methyl-[1,3]dioxan-4-one 
• 129287-50-9 (2R,5R,6R)-2-tert-Butyl-5-[(R)-hydroxy-(4-trifluoromethyl-phenyl)-methyl]-6-methyl-[1,3]dioxan-4-one 
• 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 
• 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 

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.

Optically Active Alcohols from 1,3-Dioxan-4-ones. A Practical Version of Enantioselective Synthesis with Nucleophilic Substitution at Acetal Centers

Secondary alcohols in enantiomeric excesses above 90percent are accessible from 2-substituted 6-methyl-1,3-dioxan-4-ones.The dioxanones are prepared from aldehydes and readily available (R)- or (S)-3-hydroxybutanoic acid.Treatment of the dioxanones with silyl nuclophiles or triisopropoxy(methyl)titanium in the presence of yields the corresponding 3-alkoxy acids in diastereoselectivities >/= 95percent.The 'chiral auxiliary" is removed from the alkoxy acids by treatment with LiN(i-Pr)2 to give the secondary alcohols with >/= 90percent ee. cis/trans-Mixtures (9:1) of the dioxanones furnish products of the same configurational purity as those obtained from pure cis-isomers.In comparison with other variants of enantioselective syntheses with nucleophilic substitution at acetal centers, the following advantages of the dioxanone method are noteworthy: i) (R)- and (S)-3-hydroxybutanoic acids are both readily available; ii) reactions are not sensitive to changes in conditions; iii) the 'chiral auxiliary' is removed simply by base elimination, no oxidation is required; iv) no chromatographic purification steps are necessary.The overall reaction described here is an enantioselective nucleophilic addition to aldehydes with concomitant dehydration of enantiomerically pure 3-hydroxybutanoic to crotonic acid.

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.