97465-71-9

Basic information

• Product Name: (6R)-6,7,8,9-Tetrahydro-6β,7α-dihydroxy-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione
• Synonyms: Tanshindiol C;(6R,7R)-6,7,8,9-Tetrahydro-6,7-dihydroxy-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione
• CAS NO: 97465-71-9
• Molecular Formula: C18H16O5
• Molecular Weight: 312.31664
• Mol File: 97465-71-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (6R)-6,7,8,9-Tetrahydro-6β,7α-dihydroxy-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (6R)-6,7,8,9-Tetrahydro-6β,7α-dihydroxy-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione(97465-71-9)
• EPA Substance Registry System: (6R)-6,7,8,9-Tetrahydro-6β,7α-dihydroxy-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione(97465-71-9)

Safety Data

• Hazardous Substances Data: 97465-71-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(6R)-6,7,8,9-Tetrahydro-6β,7α-dihydroxy-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione is used as a potential pharmaceutical candidate for [specific application reason, if known] due to its unique structure and stereochemistry. (6R)-6,7,8,9-Tetrahydro-6β,7α-dihydroxy-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione's ability to interact with biological systems in a specific way suggests that it may have therapeutic applications, such as targeting specific receptors or enzymes, modulating cellular pathways, or exhibiting antimicrobial properties.
Used in Chemical Research:
(6R)-6,7,8,9-Tetrahydro-6β,7α-dihydroxy-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione is used as a subject of chemical research for [specific research purpose, if known]. Its complex structure and potential for specific interactions with biological systems make it an interesting target for studies aimed at understanding its properties, mechanisms of action, and potential applications in various fields, such as drug discovery, materials science, or environmental chemistry.

Upstream product

• 930-68-7 cyclohexenone 
• 33948-36-6 2-iodocyclohex-2-en-1-one 
• 140709-89-3 2-vinylcyclohex-2-en-1-one 
• 124292-44-0 1-methyl-2-vinylcyclohex-2-en-1-ol 
• 7182-21-0 5-hydroxy-3-methylbenzo<1.2-b>furan 
• 113297-21-5 4,5-dihydro-3-methylbenzo[1,2-b]furan-4,5-dione 
• 96839-29-1 6-hydroxy-1,6-dimethyl-6,7,8,9-tetrahydrophenanthro[1,2-b]furan-10,11-dione 
• 77769-21-2 1,6-dimethyl-8,9-dihydrophenanthro[1,2-b]furan-10,11-dione 
• 96839-30-4 (±)-tanshindiol C 
• 127758-21-8 (-)-(5R,6S)-5,6-dihydroxy-6-methyl-1-vinylcyclohexene 5,6-acetonide 
• 118950-03-1 tanshindiol B acetonide 

Downstream Products

• 96839-30-4 (+)-(3S,4S)-tanshindiol C 
• 96839-30-4 tanshindiol C 

Relevant articles and documents

Total synthesis of (±)-tanshinol B, tanshinone I, and (±)-tanshindiol B and C

A concise and efficient approach was established for the divergent total synthesis of (±)-tanshindiol B and C and tanshinone I from a ubiquitous ene intermediate in 1-2 steps. This critical intermediate was derived from (±)-tanshinol B, which was synthesized in 50% overall yield over 3 steps using an ultrasound-promoted cycloaddition as a key step. Compared to a previously reported strategy, our approach is more step-economic, thus greatly improving the synthetic efficiency. The bioactivity evaluation indicates that the diol stereochemistry of the tanshidiols has an impact on the EZH2 inhibitory activity.

Asymmetric Syntheses of Salvia miltiorrhiza Abietanoid o-Quinones: Methyl Tanshinonate, Tanshinone IIB, Tanshindiol B, and 3-Hydroxytanshinone

The Diels-Alder reaction of 3-methyl-4,5-benzofurandione with vinylcyclohexene derivatives using either high-pressure or ultrasound promotion has led to the asymmetric synthesis of methyl tanshinonate, tanshinone IIB, tanshindiol B, and 3-hydroxytanshinone.The abietanoid diterpenes are active constituents of the Chinese traditional medicine, Dan Shen, prepared from the roots of Salvia miltiorrhiza Bunge.As a result, the absolute stereochemistry of these natural products has been assigned: (-)-(4S)-methyl tanshinonate, (-)-(4S)-tanshinone IIB, (-)-(3S,4R)-tanshindiol B, and (+)-(3S)-3-hydroxytanshinone.

Ultrasound-Promoted Cycloadditions in the Synthesis of Salvia miltiorrhiza Abietanoid o-Quinones

The ultrasound-promoted Diels-Alder reaction of 3-methyl-4,5-benzofurandione with appropriately substituted vinylcyclohexenes has led to the synthesis of tanshinone IIA, nortanshinone, tanshindiol B, methyl tanshinonate, and tanshinone IIB, biologically active metabolites of the Chinese traditional medicine, Dan Shen, prepared from the roots of Salvia miltiorrhiza Bunge.Methyltanshinquinone, the dihydro derivative of the natural product, methylenetanshinquinone, was similarly prepared.The effect of ultrasound in promoting the cycloadditions parallels that of high pressure and improved the regioselectivity in favour of the natural isomers.