175671-32-6

Usage

Molecular structure

A complex structure derived from indene, a bicyclic aromatic hydrocarbon.

Type of compound

An aldehyde, due to the presence of a carbonyl group.

Ring system

A six-membered ring fused to a five-membered ring.

Functional group

A carboxaldehyde group attached to the indene ring system.

Potential applications

Utilized in organic synthesis and chemical research due to its unique structure and potential reactivity.

Stereochemistry

(3aR,4R,7aR), indicating the compound's orientation in three-dimensional space, which is important for understanding its chemical behavior and applications.

Upstream product

• 1334145-28-6 C₁₀H₁₄O 
• 159428-60-1 (2E,7E)-2,7,9-Decatrien-1-ol 
• 74930-35-1 hepta-4(E),6-dienecarbonitrile 
• 74930-36-2 (5E)-5,7-octadienal 
• 2409-89-4 methyl (2E,7E)-2,7,9-decatrien-1-oate 

Relevant academic research and scientific papers

Asymmetric intramolecular Diels-Alder reactions of trienals catalyzed by chiral ruthenium Lewis acids

Chiral single-point binding ruthenium Lewis acid catalysts [Ru(acetone)((S,S)-BIPHOP-F)(Cp)][SbF6] ((S,S)-1a) and [Ru(acetone)((S,S)-BIPHOP-F)(indenyl)][SbF6] ((S,S)-1b) efficiently catalyze intramolecular Diels-Alder (IMDA) reactions of trienals under mild conditions to afford the endo cycloaddition products as the major products in good yields with high diastereo-and enantioselectivities. Schweizerische Chemische Gesellschaft.

Intramolecular Diels-Alder reactions using chiral ruthenium Lewis acids and application in the total synthesis of ent-ledol

One-point binding chiral ruthenium Lewis acids incorporating the C 2-symmetric electron-poor bidentate phosphinite ligand BIPHOP-F and a Cp or an indenyl 'roof' can efficiently catalyze asymmetric intramolecular Diels-Alder reactions of trienes to form bicyclic adducts with good to excellent asymmetric induction. This reaction forms the key step in a total synthesis of ent-ledol in 96% ee. The synthesis also helps to clarify the stereochemical assignment of ledol and inconsistencies in the measured optical rotation.

Chiral ruthenium lewis acid catalyzed intramolecular diels - Alder reactions

Single point binding ruthenium Lewis acid catalysts [Ru(acetone)(S,S)- BIPHOP-F)Cp][SbF6] ((S,S)-1b) and [Ru(acetone)(S,S)-BIPHOP-F) (indenyl)][SbF6] ((S,S)-1c) efficiently catalyze intramolecular Diels - Alder (IMDA) reactions under mild conditions to afford the endo cycloaddition products as the major product in excellent yields with high diastereo- and enantioselectivities.