116836-35-2

Basic information

• Product Name: 3-Octanol, acetate, (3S)-
• CAS NO: 116836-35-2
• Molecular Formula: C10H20O2
• Molecular Weight: 172.268
• Mol File: 116836-35-2.mol

Chemical Properties

• CAS DataBase Reference: 3-Octanol, acetate, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Octanol, acetate, (3S)-(116836-35-2)
• EPA Substance Registry System: 3-Octanol, acetate, (3S)-(116836-35-2)

Safety Data

• Hazardous Substances Data: 116836-35-2(Hazardous Substances Data)

Upstream product

• 589-98-0 (S)-octan-3-ol 
• 108-24-7 acetic anhydride 
• 557-20-0 diethylzinc 
• 66-25-1 hexanal 
• 108-05-4 vinyl acetate 
• 589-98-0 rac-3-octanol 
• 79-03-8 propionyl chloride 
• 108-22-5 Isopropenyl acetate 
• 106-68-3 3-octanone 
• 74403-67-1 rac-3-octyl sulfate 

Relevant articles and documents

An amino alcohol ligand for highly enantioselective addition of organozinc reagents to aldehydes: Serendipity rules

(matrix presented) Amino alcohol 4 (or its enantiomer) is prepared in two simple steps. Commercial (1R,2S)-2-amino-1,2-diphenylethanol is dialkylated with bis(2-bromoethyl) ether. Subsequent hydrogenation over 5% Rh on alumina in the presence of morpholine unexpectedly stops at the hexahydro derivative 4. Amino alcohol 4 promotes the enantioselective addition of diethylzinc to aldehydes at room temperature in up to 99% enantiomeric excess.

Practical synthesis of (S)-(+)-3-octanol by lipase-catalyzed enantioselective acetylation

(S)-(+)-3-Octanol (S)-1 was prepared in high enantiomeric excess through catalyzed acetylation of racemic alcohol 1 by using lipase from Candida antarctica (Chirazyme L-2) in the presence of vinyl acetate in toluene at 30°C. The pure (S)-1 was obtained in 73% isolated yield with 62% conversion. Moreover, acetate (R)-2 was converted to (S)-1 via mesylation and followed by hydrolysis using sodium bicarbonate solution in 44% yield. Copyright Taylor & Francis Group, LLC.

Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols

(Chemical Equation Presented) Racemization wanted: The dynamic kinetic resolution of secondary alcohols can be achieved by a simple and readily available catalyst system. Substrate racemization is effected at room temperature by a combination of (racemic) 1,1′-bi-2-naphthol (binol) or 2,2′-biphenol with AIMe3, and a lipase performs enantiospecific acylation (see scheme).

MIB: An advantageous alternative to DAIB for the addition of organozinc reagents to aldehydes

3-exo-Morpholinoisoborneol (MIB) catalyzes the addition of organozinc reagents to aldehydes in high enantiomeric excess and provides several advantages over the venerable amino alcohol ligand DAIB.

A stereoselective inverting sec -alkylsulfatase for the deracemization of sec -alcohols

A metallo-β-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to >99% ee via a chemoenzymatic deracemization protocol on a preparative scale.