249730-06-1

Basic information

• Product Name: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-methyl-, (1S,2S,3R,4R)-
• CAS NO: 249730-06-1
• Molecular Formula: C9H12O
• Molecular Weight: 136.194
• Mol File: 249730-06-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-methyl-, (1S,2S,3R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-methyl-, (1S,2S,3R,4R)-(249730-06-1)
• EPA Substance Registry System: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 3-methyl-, (1S,2S,3R,4R)-(249730-06-1)

Safety Data

• Hazardous Substances Data: 249730-06-1(Hazardous Substances Data)

Upstream product

• 123-73-9 trans-Crotonaldehyde 
• 542-92-7 cyclopenta-1,3-diene 
• 123-73-9 crotonaldehyde 

Relevant articles and documents

Organocatalysis using protonated 1,2-diamino-1,2-diphenylethane for asymmetric Diels-Alder reaction

Bisammonium salts of mono-N-alkylated chiral 1,2-diamino-1,2-diphenylethane (DPEN) were employed in the catalytic and asymmetric Diels-Alder reaction between cyclopentadiene and crotonaldehyde. The N-3-pentyl diamine·2HCl catalyst shows high endo/exo selectivity and endo-enantioselectivity for the cycloaddition, and this organocatalysis is the first example of the use of a chiral 1,2-diamine to generate an imine intermediate which is activated by an internal ammonium Br?nsted acid for the cycloaddition in a wet solvent.

Synthesis of MacMillan catalyst modified with ionic liquid as a recoverable catalyst for asymmetric Diels-Alder reaction

MacMillan catalyst was modified with imidazolium ionic liquid by ester linkage and acts as recoverable and reusable catalyst for asymmetric Diels-Alder reactions. A Diels-Alder reaction between cyclopentadiene and crotonaldehyde was carried out using MacMillan catalyst modified with ionic liquid (5 mol%) using trifluoroacetic acid (5 mol%) as co-catalyst in acetonitrile-water (95 : 5) at room temperature, to give 94% conversion of Diels-Alder adduct with exo/endo (1 : 1.1) and 90% ee of endo product. The catalyst was recovered and reused up to 5 cycles with a slight decrease in ee and product conversion.

Enantioselective Diels-Alder reactions of enals: Fighting species multiplicity of the catalyst with donor solvents

Chiral Lewis acids obtained from reactions of N-arylsulphonylamino acids with borane adducts effectively catalyze Diels-Alder additions of α,β-unsaturated aldehydes. Maximum enantioselectivity (methacrylaldehyde: 86 %ee, crotonaldehyde: 81 %ee) was achieved in donor solvents. The first results with new chiral Lewis acids derived from C2-symmetric N-sulphonyl derivatives of 2,2'-diamino-1,1'-binaphthyl are also presented.