13161-79-0

Basic information

• Product Name: noracronycine
• Synonyms: noracronycine;3,12-Dihydro-6-hydroxy-3,3,12-trimethyl-7H-pyrano[2,3-c]acridin-7-one;3,3,12-Trimethyl-6-hydroxy-3H-pyrano[2,3-c]acridine-7(12H)-one;Noracronine
• CAS NO: 13161-79-0
• Molecular Formula: C₁₉H₁₇NO₃
• Molecular Weight: 307.34318
• Mol File: 13161-79-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 524.2°Cat760mmHg
• Flash Point: 270.8°C
• Appearance: /
• Density: 1.271g/cm³
• Vapor Pressure: 1.32E-11mmHg at 25°C
• Refractive Index: 1.637
• CAS DataBase Reference: noracronycine(CAS DataBase Reference)
• NIST Chemistry Reference: noracronycine(13161-79-0)
• EPA Substance Registry System: noracronycine(13161-79-0)

Safety Data

• Hazardous Substances Data: 13161-79-0(Hazardous Substances Data)

Usage

Description

his acridinone alkaloid yields bright yellow needles when crystallized from AcOEt or C6H6. It is a very weak base and does not form stable salts. It is insoluble in alkalies and gives no reaction with CHlNl . With methyl sulphate and potassium carbonate, however, it is methylated, giving Acronycine (q.v.). The ultraviolet spectrum has absorption maxima at 255 and 285 mfJ. with shoulders at 305-310 and 410-415 mfJ., there also being an inflexion at 293 mfJ.. The p_x0002_toleuenesulphonate has been prepared as short, yellow needles from C6H6-light petroleum, m.p. l76-8°C. With FeC13 the alkaloid gives a deep green colour.

References

Govindachari, Pai, Subramaniam., Tetrahedron, 22, 3245 (1966)

InChI:InChI=1/C19H17NO3/c1-19(2)9-8-12-15(23-19)10-14(21)16-17(12)20(3)13-7-5-4-6-11(13)18(16)22/h4-10,21H,1-3H3

Upstream product

• 2190-48-9 3-chloro-3-methyl-1-butene 
• 85-91-6 Methyl N-methylanthranilate 
• 13396-93-5 6-Hydroxy-3,3-dimethyl-3,12-dihydro-7H-pyrano<2,3-c>acridin-7-one 
• 74-88-4 methyl iodide 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 28333-02-0 N-methyl-1,3-dihydroxyacridone 
• 20324-10-1 1,3-dihydroxyacridin-9(10H)-one 
• 16718-49-3 1-hydroxy-4-(3-hydroxy-3-methyl-butyl)-3-methoxy-10H-acridin-9-one 
• 16727-39-2 6-hydroxy-3,3-dimethyl-1,2,3,12-tetrahydro-pyrano[2,3-c]acridin-7-one 
• 70509-95-4 6-methoxy-3,3,12-trimethyl-3,12-dihydro-pyrano[2,3-c]acridin-7-one; hydrochloride 
• 128810-87-7 1,2,3,12-tetrahydro-2,6-dihydroxy-3,3,12-trimethyl-7H-pyrano<2,3-c>acridin-7-one 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 28333-13-3 1,3-dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinone (glyocitrine-II) 
• 1111-97-3 3-chloro-3-methylbut-1-yne 

Downstream Products

• 17014-70-9 1,2-dihydronoracronycine 
• 13255-09-9 3,3,12-trimethyl-6-[[(4-methylphenyl)sulfonyl]oxy]-3H,7H-pyrano[2,3-c]acridin-7-one 
• 7008-42-6 acronine 
• 36380-14-0 3,12-Dihydro-6-acetoxy-3,3,12-trimethyl-7H-pyrano<2,3-c>acridin-7-on 

Relevant articles and documents

Acetylene Chemistry, Part XXII: Synthesis of Noracronycine and Some of its Analogs via Mitsunobu-Reaction

The natural product noracronycine as well as some of its analogs were synthesized by Mitsunobu-etherisation, using propinol derivatives.Keywords.Acridone alkaloids; Analogs of noracronycine; Chromene synthesis; Noracronycine; Mitsunobu-etherisation.

Total synthesis of acronycine and noracronycine: An aryne amination approach

Acronycine and noracronycine are chromene-containing alkaloids with significant biological activity. We have accomplished a concise total synthesis of acronycine and noracronycine. The key step, regioselective nucleophilic addition of anthranilate to chromene-type arynes under mild and transition-metal-free conditions was achieved. In addition, further modifications of nucleophilic addition products, such as hydrogenation, O-functionalization and palladium-catalyzed coupling reactions have also been developed, providing a concise procedure for these alkaloids and their derivatives.

New synthetic routes to acronycine, noracronycine, and their analogues

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New acridone derivatives obtained by heating the HCl salt of acronycine

By heating the HCl salt of acronycine (1), the new acridone derivatives (6, 9, 13 and 15) were obtained together with noracronycine (2), dihydronoracronycine (3), 1,3-dihydroxy-10-methylacridone (4) and (5). Compound (5), one of the main products of this reaction, is a linear type dihydro derivative of 2, compound (9) is a furanoacridone derivative with a geminal methyl group and compound (15) is a derivative of 5 with an additional C5 unit.