172589-32-1

Basic information

• Product Name: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, trans- (9CI)
• Synonyms: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, trans- (9CI)
• CAS NO: 172589-32-1
• Molecular Formula: C9H14O2
• Molecular Weight: 154.20626
• Product Categories: ALDEHYDE
• Mol File: 172589-32-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, trans- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, trans- (9CI)(172589-32-1)
• EPA Substance Registry System: 3-Cyclohexene-1-carboxaldehyde, 2-methoxy-1-methyl-, trans- (9CI)(172589-32-1)

Safety Data

• Hazardous Substances Data: 172589-32-1(Hazardous Substances Data)

Upstream product

• 78-85-3 2-methylpropenal 
• 10034-09-0 1-methoxy-1,3-butadiene 
• 3036-66-6 1-methoxybuta-1,3-diene 

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.

Chiral titanium complex-catalyzed Diels-Alder reaction: A practical route to anthracycline intermediates

Asymmetric Diels-Alder reactions of methacrolein and 1,4-naphthoquinone with 1,3-dienol derivatives catalyzed by the chiral binaphthol (BINOL)-derived titanium complex 1 are shown to provide the corresponding endo-adducts in high enantiomeric purity. The

Diels-Alder reactions: Rate acceleration promoted by a biphenylenediol

The presence of biphenylenediol 8 accelerates the rate of some Diels-Alder reactions. Catalysis via a complex involving two hydrogen bonds (see 6) is proposed.

The 1-Aza-Cope Rearrangement

The 1-aza-Cope rearrangement of azavinylcyclohexene derivatives were investigated.It was observed that an N-acyl substituent on the 1-aza 1,5-diene provides a sufficient driving force for this normally contrathermodynamic process.Although simple derivatives have high activation energies proceeding in relative low overall yield, a methoxy substituent at C-4 of the aza diene as well as its incorporation into strained bicyclic ring systems facilitates the 1-aza-Cope rearrangement.Because the aza diene precursors are readily available by using the Diels-Alder reaction with acrolein derivatives, this process has synthetic potential for the preparation of nitrogen heterocycles.This scheme is illustrated with the preparation of a hydrolulolidine providing a formal total synthesis of (+/-)-aspidospermine.