(1R,4R,8R)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene
(1R,4R,8R)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene (CAS 948594-95-4) is a chiral bicyclic diene with the molecular formula C22H30O and a molecular weight of 310.47 g/mol. This compound is primarily utilised as a ligand in asymmetric synthesis, specifically for performing enantioselective conjugate additions. Its unique structure enables high selectivity in reactions involving unsaturated esters and aldehydes when employed with rhodium precatalysts.
- IUPAC
- (1R,4R,8R) Carreira DOLEFIN Ligand,(1R,4R,8R)-8-Methoxy-1,8-dimethyl-2-(2-methylpropyl)-5-(phenylmethyl)bicyclo[2.2.2]octa-2,5-diene
- Synonyms
- (1R,4R,8R)-8-Methoxy-1,8-dimethyl-2-(2-methylpropyl)-5-(phenylmethyl)bicyclo[2.2.2]octa-2,5-diene8-dimethylbicyclo[2.2.2]octa-2,5-diene,948594-95-4, C22H30O
![(1R,4R,8R)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene (C22H30O) — chemical structure, CAS 948594-95-4; Chemistry, fine chemical supplied by Tech Serve Solutions](/_next/image?url=https%3A%2F%2Fpub-f4d920c906024441a773a96f7098e551.r2.dev%2Fimages%2Fproducts%2F948594-95-4.png&w=3840&q=75)
Asymmetric Conjugate Addition
This ligand, when complexed with rhodium precatalysts, facilitates enantioselective conjugate addition reactions. It is particularly effective for unsaturated esters and aldehydes, enabling the synthesis of chiral building blocks.
Chiral Ligand in Catalysis
As a chiral catalyst component, it plays a crucial role in stereoselective transformations. Its application is key in methodologies requiring precise control over enantiomeric excess during synthesis.
Organic Synthesis Reagent
It serves as a valuable reagent in advanced organic synthesis, contributing to the construction of complex molecules with defined stereochemistry.
| Molecular weight | 310.47 |
|---|---|
| Empirical formula | C22H30O |
| Assay | 95% |
| Refractive index | n20/D 1.5205 |
| Optical activity | [α]20/D +98±5°, c = 0.7 in chloroform |
| Application | When used in conjunction with Rh precatalysts, selectively perform asymmetric conjugate addition to unsaturated esters and aldehydes.1,2 |
| Protective equipment | Eyeshields, Gloves |
|---|---|
| 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 (1R,4R,8R)-5-Benzyl-2-isobutyl-8-methoxy-1,8-dimethylbicyclo[2.2.2]octa-2,5-diene used for?
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This compound is used as a chiral ligand in asymmetric synthesis, specifically for the enantioselective conjugate addition to unsaturated esters and aldehydes when employed with rhodium precatalysts.
What are the CAS number and molecular formula for this product?
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The CAS number is 948594-95-4 and the empirical formula is C22H30O.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this compound at an assay of 95%. We do not represent this product as USP, BP, EP, or any other pharmacopoeia grade.
How should this chemical be handled safely?
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Handling requires appropriate personal protective equipment, including eyeshields and gloves, due to its classification (WGK Germany: 3). Refer to the Safety Data Sheet for comprehensive guidance.
Is this product available for international export?
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Yes, Tech Serve Solutions is a global supplier and exporter of fine chemicals, and this product can be shipped internationally.
How can I request a sample or quote?
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To request a sample or a quote, please contact our sales team through the website or by phone, providing the product name and CAS number.
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