(1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene
(1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene (CAS 1063949-39-2) is a chiral organic compound with the molecular formula C15H24O. This bicyclic diene serves as a valuable reactant and chiral ligand in asymmetric synthesis. Its specific stereochemistry makes it instrumental in catalysing stereoselective reactions, particularly conjugate additions and arylations.
- IUPAC
- (1R,4R,7R)-α,α,5-Trimethyl-7-(1-methylethyl)bicyclo[2.2.2]octa-2,5-diene-2-methanol
- Synonyms
- 5-dieneC15H24O(1R,4R,7R)-α,α,5-Trimethyl-7-(1-methylethyl)bicyclo[2.2.2]octa-2,5-diene-2-methanol
![(1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene (C15H24O) — chemical structure, CAS 1063949-39-2; Chemistry, fine chemical supplied by Tech Serve Solutions](/_next/image?url=https%3A%2F%2Fpub-f4d920c906024441a773a96f7098e551.r2.dev%2Fimages%2Fproducts%2F1063949-39-2.png&w=3840&q=75)
Chiral Ligand for Asymmetric Conjugate Addition
This compound acts as a chiral ligand in asymmetric 1,4-conjugate addition reactions. It facilitates the stereoselective formation of new carbon-carbon bonds, crucial in complex molecule synthesis.
Rh-Catalyzed Asymmetric Conjugate Addition
It is employed in rhodium-catalysed asymmetric conjugate addition of boronic acids to α,β-unsaturated ketones. This application enables the enantioselective synthesis of valuable ketone derivatives.
Rhodium-Catalyzed Asymmetric Arylation
The compound is utilised in rhodium-catalysed asymmetric arylation reactions involving imines. This method allows for the enantioselective introduction of aryl groups, producing chiral amine precursors.
| Molecular weight | 220.35 |
|---|---|
| Empirical formula | C15H24O |
| Density | 0.952 g/mL at 25 °C |
| Refractive index | n20/D 1.495 |
| Optical activity | [α]22/D +42.0°, c = 0.5 in chloroform |
| Application | Reactant for:• Chiral ligand for asymmetric 1,4-conjugate addition1Used for:• Rh-catalyzed asymmetric conjugate addition reaction of boronic acids to α,β-unsaturated ketones2• Rhodium-catalyzed asymmetric arylation of imines3 |
Hazard statements
- H302Harmful if swallowed
- H400Very toxic to aquatic life
Precautionary statements
- P273Avoid release to the environment
| Transport (UN / ADR) | UN 3077 9 / PGIII |
|---|---|
| Water hazard class (WGK, DE) | 2 |
| Hazard codes (EU) | Xn,N |
| Risk statements (R) | 22-50/53 |
| Safety statements (S) | 60-61 |
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,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene used for?
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This compound is used as a chiral ligand for asymmetric 1,4-conjugate addition reactions and in Rh-catalyzed asymmetric conjugate addition of boronic acids to α,β-unsaturated ketones, as well as Rh-catalyzed asymmetric arylation of imines.
What is the CAS number and molecular formula?
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The CAS number is 1063949-39-2, and the molecular formula is C15H24O.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical with a purity indicated by its refractive index (n20/D 1.495) and density (0.952 g/mL at 25 °C). It is supplied as a research or technical grade; TSS does not represent it as USP, BP, or EP grade.
How should this chemical be handled?
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This compound is classified as harmful if swallowed (H302) and is very toxic to aquatic life with long-lasting effects (H400). Handle with appropriate personal protective equipment and avoid release into the environment (P273). Refer to the Safety Data Sheet for full handling information.
Is this chemical a controlled substance?
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The provided data does not indicate that this chemical is a controlled substance.
How can I get a quote or sample?
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To request a quote or sample, please contact our sales team through the website or by phone. Provide the product name and CAS number for prompt service.
How is this chemical shipped and exported?
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This chemical is shipped and exported according to international regulations, identified as UN 3077, Class 9, Packing Group III. Specific shipping details can be confirmed upon order.
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