(S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione
(S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione (CAS: 33878-99-8), a chiral building block with the molecular formula C11H14O2, is a key intermediate in complex organic synthesis. Its structure makes it valuable for constructing intricate molecular architectures, particularly in the fields of natural product synthesis and asymmetric methodologies. Tech Serve Solutions supplies this compound for advanced research and development applications.
- IUPAC
- (S)-Miescher-Wieland ketone,(S)-(+)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione,(S)-(+)-9-Methyl-5(10)-octaline-1,6-dione,Wieland-Miescher ketone
- Synonyms
- 8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione(S)-Miescher-Wieland ketone(S)-(+)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione(S)-(+)-9-Methyl-5(10)-octaline-1,6-dioneWieland-Miescher ketone
Natural Product Synthesis
This compound serves as a crucial intermediate in the total synthesis of macrocyclic diterpene lactones, such as (+)-cleomeolide. Its chiral nature is essential for constructing the complex stereochemistry of these natural products.
Asymmetric Synthesis
It functions as a chiral building block for enantioselective synthetic routes, notably in approaches to the A and C rings of taxol. This highlights its utility in creating specific stereoisomers of target molecules.
Catalysis Research
The compound has been employed in studies investigating the selective hydrogenation of alpha,beta-unsaturated ketones. This research explores the efficacy of novel palladium complexes as catalysts for such transformations.
| Molecular weight | 178.23 |
|---|---|
| Empirical formula | C11H14O2 |
| Assay | 98% |
| Optical activity | [α]20/D +98°, c = 1.1 in benzene |
| Application | Key intermediate in the total synthesis of the macrocyclic diterpene lactone, (+)-cleomeolide.1,2 Chiral building block for enantioselective approaches to the A and C rings of taxol.3,4,5 Used to study selective hydrogenations of the carbon-carbon double bonds in α,β-unsaturated ketones with a new class of palladium complexes as catalysts.6 |
| Melting point | 50-52 °C(lit.) |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is (S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione used for?
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It is used as a key intermediate in the total synthesis of natural products like (+)-cleomeolide and as a chiral building block for enantioselective syntheses, including approaches to taxol. It is also used in catalysis research for selective hydrogenations of unsaturated ketones.
What is the CAS number and molecular formula for this compound?
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The CAS number is 33878-99-8, and the molecular formula is C11H14O2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical with an assay of 98%. We do not represent it as USP, BP, EP, or other pharmacopoeia grades unless explicitly stated in the product data.
How should (S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione be handled?
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Handle with appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter is recommended. It is classified under WGK 2 in Germany.
Is this product available for export?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, pharmaceutical intermediates, and laboratory reagents.
How can I request a sample or quote?
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Please contact our sales team through the website or by phone to request a sample or a formal quotation for this product.
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