132455-66-4

Basic information

• Product Name: syn-4-(phenylhydroxymethyl)-3-hexanone
• CAS NO: 132455-66-4
• Molecular Weight: 206.285
• Mol File: 132455-66-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: syn-4-(phenylhydroxymethyl)-3-hexanone(CAS DataBase Reference)
• NIST Chemistry Reference: syn-4-(phenylhydroxymethyl)-3-hexanone(132455-66-4)
• EPA Substance Registry System: syn-4-(phenylhydroxymethyl)-3-hexanone(132455-66-4)

Safety Data

• Hazardous Substances Data: 132455-66-4(Hazardous Substances Data)

Upstream product

• 134435-90-8 (C₆H₁₁)2(OC(Et)CHCH₂Me)borane 
• 100-52-7 benzaldehyde 
• 50396-96-8 E-4-hexen-3-one 

Relevant articles and documents

Stereoselective 1,4-hydroboration of acyclic (E)-α,β-unsaturated ketones with dialkylboranes. Synthesis of (Z)-vinyloxyboranes

Dialkylboranes add to acyclic disubstituted (E)-α,β-unsaturated ketones in a 1,4-fashion affording (Z)-vinyloxyboranes as major or sole products. The stereochemical outcome of the hydroboration reaction is consistent with a concerted pericyclic mechanism. The intermediate vinyloxyboranes can be trapped with aldehydes to give virtually pure syn β-hydroxyketones.

A New Approach to (Z)-Vinyloxyboranes via 1,4 Hydroboration of (E)-α,β-Unsaturated Ketones. Synthesis of syn Aldols

(Z)-Vinyloxy boranes are obtained via 1,4-hydroboration of acyclic disubstituted (E)-α,β-unsaturated ketones with dicyclohexylborane or diisopinocampheylborane in tetrahydrofuran, CH2Cl2 or CHCl3 at 20 deg C; treatment of the hydroboration mixture with an aldehyde allows pure syn aldols to be synthesized in good yields, and in excellent enantiomeric excesses, using the latter borane.