404909-58-6

Basic information

• Product Name: (S)-1-(3-BROMO-1,4-DIMETHOXY-NAPHTHALEN-2-YL)-PROPAN-2-OL
• Synonyms: (S)-1-(3-BROMO-1,4-DIMETHOXY-NAPHTHALEN-2-YL)-PROPAN-2-OL;(S)-1-(3-Bromo-1,4-dimethoxy-naphthalen-2-yl)-
• CAS NO: 404909-58-6
• Molecular Formula: C15H17BrO3
• Molecular Weight: 0
• Mol File: 404909-58-6.mol

Chemical Properties

• Boiling Point: 438°C at 760 mmHg
• Flash Point: 218.7°C
• Appearance: /
• Density: 1.384g/cm³
• Vapor Pressure: 1.91E-08mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: (S)-1-(3-BROMO-1,4-DIMETHOXY-NAPHTHALEN-2-YL)-PROPAN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(3-BROMO-1,4-DIMETHOXY-NAPHTHALEN-2-YL)-PROPAN-2-OL(404909-58-6)
• EPA Substance Registry System: (S)-1-(3-BROMO-1,4-DIMETHOXY-NAPHTHALEN-2-YL)-PROPAN-2-OL(404909-58-6)

Safety Data

• Hazardous Substances Data: 404909-58-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H17BrO3/c1-9(17)8-12-13(16)15(19-3)11-7-5-4-6-10(11)14(12)18-2/h4-7,9,17H,8H2,1-3H3/t9-/m0/s1

Upstream product

• 876-27-7 4-chlorophenyl acetate 
• 404908-62-9 3-bromo-2-(2-hydroxypropyl)-1,4-dimethoxynaphthalene 
• 90-15-3 α-naphthol 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 80089-60-7 2-allyl-3-bromo-1,4-dimethoxy-naphthalene 
• 404909-81-5 3-bromo-2-(2'-oxopropyl)-1,4-dimethoxynaphthalene 
• 109297-44-1 2-allyl-3-bromo-1,4-naphthoquinone 

Relevant articles and documents

Chemoenzymatic synthesis of deoxy analogues of the DNA topoisomerase II inhibitor eleutherin and the 3C-protease inhibitor thysanone

The asymmetric synthesis of (-)-9-demethoxyeleutherin 6, (+)-9-demethoxyeleutherin 7 and (+)-7,9-deoxythysanone 8 has been achieved using a microwave assisted kinetic resolution of racemic alcohol 11 with Novozyme 435 as the key step.

The influence of microwave irradiation on lipase-catalyzed kinetic resolution of racemic secondary alcohols

The influence of microwave irradiation on the Novozyme 435 (Candida antarctica lipase) catalyzed kinetic resolution of secondary alcohols with different functional groups was studied in comparison to the use of conventional heating at 60 °C. p-Chlorophenyl acetate was used as an acyl donor and toluene as the solvent. (±)-1-Phenyl-1-propanol 1, (±)-1-(4-bromophenyl)-propan-1-ol 3, (±)-1-phenylbut-3-en-1-ol 5 and (±)-3-bromo-2-(2-hydroxypropyl)-1,4-dimethoxynaphthalene 7 were successfully resolved into their (S)-alcohols and (R)-esters, respectively, in good enantiomeric excess. Resolution of (±)-ethyl-5-(4-methoxybenyloxy)-3-hydroxypentanoate 9 afforded its (R)-alcohol and (S)-ester using this method. In addition, microwave-assisted lipase transesterification of meso-symmetric diol 11 effected desymmetrization to ester 12 with high enantiomeric excess. In all cases studied, the conversion value for the microwave-assisted lipase kinetic resolution of secondary alcohols was higher than that obtained using conventional heating.

Stereoselective synthesis of deoxy analogues of the 3C-protease inhibitor thysanone

The synthesis of racemic 7,9-dideoxythysanone 9 was achieved starting from allylnaphthalene 5 via epoxidation and reduction to bromoalcohol 7. Subsequent lithiation of the bromide and quenching with DMF afforded lactol 8 which underwent clean oxidative demethylation to racemic 6,8-dideoxythysanone 9. The synthesis of (1R,3S)-(+)-7,9-dideoxythysanone 9 was then achieved albeit in low ee, starting from (R)-epoxide 6 which in turn was obtained via Sharpless asymmetric dihydroxylation of allylnaphthalene 5. An improved asymmetric synthesis of (1S,3R)-(+)-7,9-dideoxythysanone 9 in 72% ee was then accomplished starting from (R)-bromoalcohol 7 which was obtained via asymmetric reduction of ketone 12 using a modified chiral oxazaborolidine. The key ketone 12 in turn was prepared by Wacker oxidation of allylnaphthalene 5.