155976-20-8

Basic information

• Product Name: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, (1S-trans)- (9CI)
• Synonyms: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, (1S-trans)- (9CI)
• CAS NO: 155976-20-8
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.20626
• Product Categories: ALDEHYDE
• Mol File: 155976-20-8.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, (1S-trans)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, (1S-trans)- (9CI)(155976-20-8)
• EPA Substance Registry System: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, (1S-trans)- (9CI)(155976-20-8)

Safety Data

• Hazardous Substances Data: 155976-20-8(Hazardous Substances Data)

Upstream product

• 78-85-3 2-methylpropenal 
• 10034-09-0 1-methoxy-1,3-butadiene 

Relevant articles and documents

Asymmetric catalysis of Diels-Alder cycloadditions by an MS-free binaphthol-titanium complex: Dramatic effect of MS, linear vs positive nonlinear relationship, and synthetic applications

Asymmetric Diets-Aider (D.-A.) reaction of 5-hydroxynaphthoquinone (juglone) with butadienyl acetate catalyzed by the binaphthol-derived chiral titanium (BINOL-Ti) complex 1 proceeds in only 9% ee in the presence of molecular sieves (MS). Remarkably, however, this reaction proceeds in 76-96% ee with BINOL-Ti complex 1 freed from MS to provide the endo-adducts useful for the synthesis of anthracyclines and tetracyclines. The solid MS-free BINOL-Ti complex 1 is stable for months at -20°C. Enhancements in endo selectivity and asymmetric induction are observed with the MS-free BINOL-Ti 1 also in the catalyzed D.-A. cycloaddition of methacrolein and glyoxylate with 1,3-dienol ethers and esters. The glyoxylate adducts can be converted to the mevinolin (compactin) intermediates. Surprisingly, the MS-free complex 1 exhibits not only a linear relationship between the ee's of BINOL-Ti 1 and the D.-A. products but also a positive nonlinear effect (asymmetric amplification), depending simply on the mixing manner of (R)-1 with (S)-1 or (±)-1.