131750-27-1

Basic information

• Product Name: 6-broMo-5,7-diMethyl-2,3-dihydro-1H-inden-1-one
• Synonyms: 6-broMo-5,7-diMethyl-2,3-dihydro-1H-inden-1-one
• CAS NO: 131750-27-1
• Molecular Formula: C11H11BrO
• Molecular Weight: 239.10844
• EINECS: -0
• Mol File: 131750-27-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-broMo-5,7-diMethyl-2,3-dihydro-1H-inden-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-broMo-5,7-diMethyl-2,3-dihydro-1H-inden-1-one(131750-27-1)
• EPA Substance Registry System: 6-broMo-5,7-diMethyl-2,3-dihydro-1H-inden-1-one(131750-27-1)

Safety Data

• Hazardous Substances Data: 131750-27-1(Hazardous Substances Data)

Upstream product

• 131750-25-9 3-(3'-bromo-2',4'-dimethylphenyl)-1-chloro-3-oxopropane 
• 576-22-7 2-Bromo-m-xylene 
• 625-36-5 2-chloropropionyl chloride 
• 576-26-1 2.6-dimethylphenol 

Downstream Products

• 60657-37-6 pterosin B 
• 39815-61-7 6-[2'-(benzoyloxy)ethyl]-(2R)-2,5,7-trimethyl-1-indanone 

Relevant articles and documents

A concise stereoselective synthesis of pterosin B

Pterosin B is a naturally occurring indanone found in bracken fern (Pteridium aquilinum) that displays a variety of interesting pharmacological properties, but for which few stereoselective syntheses exist. Herein we describe a 7-step stereoselective synthesis of (2R)-pterosin B via 6-bromo-5,7-dimethylindan-1-one whose structure was confirmed by NOE analysis and structure determination by X-ray crystallography. The hydroxyethyl chain was introduced via a Suzuki-Miyaura cross-coupling reaction. The 2-methyl group was introduced stereoselectively by methylation of a SAMP [(S)-1-amino-2-methoxymethyl)pyrrolidine] hydrazone and the chiral auxiliary was removed to produce (2R)-pterosin B. The structure of pterosin B was confirmed by specific rotation and structural determination by X-ray crystallography.

Synthesis of (±)-pterosin A via Suzuki-Miyaura cross-coupling reaction

A practical synthesis of (±)-pterosin A from commercially available 2-bromo-1,3-dimethyl-benzene 5 has been accomplished in 10% overall yield. The synthesis used Suzuki-Miyaura coupling reaction of C6-bromoindanone derivative 3 with potassium vinyltrifluoroborate 9, which provided the corresponding vinylindanone 2 in >85% yield. The vinylindanone 2 could be further elaborated to pterosin A by reduction with LAH, selective protection of primary alcohol with TESCl, hydroboration-oxidation of vinyl group, protection of primary alcohol with TIPSCl, oxidation of the secondary alcohol, and desilylation with TBAF.

Synthesis and antispasmodic activity of nature identical substituted indanes and analogues

The synthesis of a series of substituted indanes which provide routes to nature-identical compounds and their analogues is reported. The smooth muscle relaxant activity of a series of substituted indanes and indanones together with their analogues has been measured. A compound with significant smooth muscle relaxant activity has been identified.