130548-10-6

Basic information

• Product Name: (+)-Rubiginone B2
• Synonyms: (+)-Rubiginone B2;(3S)-3β-Methyl-8-methoxy-1,2,3,4,7,12-hexahydrobenzo[a]anthracene-1,7,12-trione;(S)-3,4-Dihydro-8-methoxy-3β-methylbenz[a]anthracene-1,7,12(2H)-trione;Rubiginone B2
• CAS NO: 130548-10-6
• Molecular Formula: C24H26Cl2N2O
• Molecular Weight: 429.38204
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 130548-10-6.mol

Chemical Properties

• Melting Point: >262 °C (decomp)
• Boiling Point: 540.246°C at 760 mmHg
• Flash Point: 240.156°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: (+)-Rubiginone B2(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Rubiginone B2(130548-10-6)
• EPA Substance Registry System: (+)-Rubiginone B2(130548-10-6)

Safety Data

• Hazardous Substances Data: 130548-10-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-Rubiginone B2 is used as an antibiotic agent for its potentiating activity on vincristine-cytotoxicity. This application is particularly relevant in cancer treatment, where it can enhance the effectiveness of chemotherapy drugs and potentially improve patient outcomes.
Additionally, due to its chemical properties as a pale yellow solid, (+)-Rubiginone B2 may have potential uses in other industries that require specific color characteristics or stability in solid form.

InChI:InChI=1/C20H16O4/c1-10-8-11-6-7-13-18(16(11)14(21)9-10)20(23)12-4-3-5-15(24-2)17(12)19(13)22/h3-7,10H,8-9H2,1-2H3/t10-/m0/s1

Upstream product

• 179818-48-5 8-methoxy-3-methyl-1,2,3,4-tetrahydrobenzoanthracene-7,12-dione 
• 632337-52-1 (+)-(3R)-8-methoxy-3-methyl-1,2,3,4-tetrahydrobenzo[a]anthracene-7,12-dione 
• 13368-65-5 (3R)-3-methylcyclohexanone 
• 481-39-0 5-hydroxynaphtho-1,4-quinone 
• 681001-30-9 (R)-8-hydroxy-3-methyl-1,2,3,4-tetrahydrobenz[a]anthracene-7,12-dione 
• 681001-31-0 (R)-5-methyl-1-vinylcyclohex-1-ene 
• 134916-00-0 (4S)-4-benzyl-3-(hex-5-enoyl)-1,3-oxazolidin-2-one 
• 77189-69-6 5-acetoxy-2-bromo-1,4-naphthoquinone 
• 1577-22-6 5-hexenoic acid 
• 949087-72-3 (R)-(3-vinylcyclohex-3-enyl)methyl 4-methylbenzenesulfonamide 
• 949087-71-2 (R)-2-(prop-2-ynyl)hex-5-enyl 4-methylbenzenesulfonate 
• 942513-97-5 (R)-2-(prop-2-ynyl)hex-5-en-1-ol 
• 942513-96-4 (4S)-4-benzyl-3-((R)-2-(prop-2-ynyl)hex-5-enoyl)oxazolidin-2-one 
• 28882-53-3 (S)-8-hydroxy-3-methyl-3,4-dihydrotetraphene-1,7,12(2H)-trione 

Downstream Products

• 28882-53-3 (S)-8-hydroxy-3-methyl-3,4-dihydrotetraphene-1,7,12(2H)-trione 

Relevant articles and documents

ABSOLUTE CONFIGURATION OF THE RUBIGINONES AND PHOTO-INDUCED OXIDATION OF THE C1 HYDROXYL OF THE ANTIBIOTICS TO A KETONE

The absolute stereochemistry of rubiginones A1, A2, B1, B2, C1 and C2 has been established by NMR spectral analysis using the O-methylmandelate method.A facile photoinduced oxidation of rubiginones A1, B1 and C1 to rubigignones A2, B2 and C2, respectively, is discussed in relation to the absolute stereochemistry.

Total Synthesis of the Angucylinone Antibiotic (+)-Rubiginone B 21

A new chiral synthesis of (+)-rubiginone B2 is reported. The intramolecular cobalt-mediated [2+2+2]-cycloaddition of a triyne precursor, synthesized from (+)-citronellal, afforded a chiral anthracene, which led after a two-step oxidation to the angucyclinone antibiotic.

A facile synthesis of the angucyclinone antibiotic (+)-rubiginone B 2 involving the BF3-mediated Diels-Alder reaction of juglone

A short synthesis of (+)-rubiginone B2 is reported. The BF 3-mediated Diels-Alder reaction of juglone and (R)-3-methyl-1- vinylcyclohexene followed by aromatization gave the anthraquinone as the desired regioisomer, which was converted into the target antibiotic after a two-step operation.

The cobalt way to angucyclinones: Asymmetric total synthesis of the antibiotics (+)-rubiginone B2, (-)-tetrangomycin, and ( - ) -8- O-Methyltetrangomycin

A cobalt(I)-mediated convergent and asymmetric total synthesis of angucyclinones with an aromatic B ring has been developed. In the course of our research, we synthesized three naturally occurring anguclinone derivatives, namely, (+)-rubiginone B2/s

Angucyclinone antibiotics: Total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755

(Chemical Equation Presented) A concise and highly enantioselective route has been developed for the synthesis of angucyclinone-type natural products. Utilizing this strategy, total syntheses of five natural products YM-181741, (+)-ochromycinone, (+)-rubi

Efficient method for synthesis of angucyclinone antibiotics via gold-catalyzed intramolecular [4 + 2] benzannulation: Enantioselective total synthesis of (+)-ochromycinone and (+)-rubiginone B2

An efficient synthetic approach to angucyclinone antibiotics, (+)-ochromycinone and (+)-rubiginone B2, is reported. The key step involves the facile formation of 2,3-dihydrophenantren-4(1H)-one skeleton, an important framework of angucyclinone

Short and efficient enantioselective total synthesis of angucyclinone type antibiotics (+)-rubiginone B2 and (+)-ochromycinone

The enantioselective total synthesis of antibiotics rubiginone B2 and ochromycinone is achieved from enantiopure (S)-5-methoxy-2-(p-tolylsulfinyl)-1,4-naphthoquinone and a racemic vinylcyclohexene through a short sequence involving a tandem Diels-Alder reaction-sulfoxide elimination process with simultaneous kinetic resolution of the racemic diene, followed by controlled aromatization and functional group deprotection.