1063949-39-2

Basic information

• Product Name: (1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene
• Synonyms: (1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene
• CAS NO: 1063949-39-2
• Molecular Formula: C15H24O
• Molecular Weight: 220.35046
• Mol File: 1063949-39-2.mol

Chemical Properties

• Boiling Point: 303.0±11.0 °C(Predicted)
• Appearance: /
• Density: 0.952 g/mL at 25 °C
• Refractive Index: n20/D1.495
• PKA: 14.85±0.29(Predicted)
• CAS DataBase Reference: (1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene(1063949-39-2)
• EPA Substance Registry System: (1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene(1063949-39-2)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 2
• Hazardous Substances Data: 1063949-39-2(Hazardous Substances Data)

Usage

Uses

1. Used in Chemical Synthesis:
(1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene is used as a chiral ligand for asymmetric 1,4-conjugate addition reactions. Its unique structure allows for the selective formation of desired products with high enantioselectivity and diastereoselectivity, making it a valuable tool in the synthesis of complex organic molecules.
2. Used in Pharmaceutical Industry:
(1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene is used as a reactant in the development of new pharmaceutical compounds. Its chiral nature and unique structural features make it a promising candidate for the synthesis of novel drugs with improved efficacy and selectivity.
3. Used in Catalyst Development:
In the field of catalysis, (1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2.2.2]octa-2,5-diene is used for the development of new catalysts, particularly in Rh-catalyzed asymmetric conjugate addition reactions of boronic acids to α,β-unsaturated ketones. Its chiral properties enable the creation of catalysts that can selectively promote specific reactions, leading to the formation of desired products with high enantiomeric purity.
4. Used in Asymmetric Arylation of Imines:
(1R,4R,7R)-7-Isopropyl-2-(1-hydroxy-1-methylethyl)-5-methylbicyclo[2,2,2]octa-2,5-diene is also used in the Rhodium-catalyzed asymmetric arylation of imines. This application takes advantage of the compound's chiral centers and structural features to facilitate the formation of enantiomerically enriched products, which are essential in the synthesis of biologically active molecules and pharmaceuticals.

Upstream product

• 1063949-34-7 (1R,4R,7R)-methyl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate 
• 74-88-4 methyl iodide 
• 1188966-75-7 (1R,4R,7R)-naphthalen-2-yl 7-isopropyl-5-methylbicyclo[2.2.2]octa-2,5-diene-2-carboxylate 
• 917-54-4 methyllithium 

Relevant articles and documents

Electronic and steric tuning of chiral diene ligands for rhodium-catalyzed asymmetric arylation of imines

Rhodium-catalyzed asymmetric arylation of imines using electronically and sterically-modified chiral diene ligands gave the corresponding diarylmethylamines in high yield and with high enantioselectivity using just 0.3 mol% of catalyst.

Simple chiral diene ligands provide high enantioselectivities in transition-metal-catalyzed conjugate addition reactions

(Chemical Equation Presented) Chiral dienes possessing the bicyclo[2.2.2]octadiene framework were prepared readily through the [4 + 2] cycloaddition of (R)-α-phellandrene with methyl propiolate as the key step. Diene 9, substituted with a tertiary alcohol