Noracronycine

Base Information

• Chemical Name: Noracronycine
• CAS No.: 13161-79-0
• Molecular Formula: C19H17 N O3
• Molecular Weight: 307.34318
• Hs Code.: 2934999090
• NSC Number: 103005
• UNII: O4TQA37UF4
• DSSTox Substance ID: DTXSID50157139
• Nikkaji Number: J14.917I
• Wikidata: Q83025275
• Metabolomics Workbench ID: 140838
• ChEMBL ID: CHEMBL509922
• Mol file: 13161-79-0.mol

Synonyms:3,12-dihydro-6-hydroxy-3,3,12-trimethyl-7H-pyrano(2,3-c)acridin-7-one;noracronine;noracronycine

Chemical Property of Noracronycine

Chemical Property:

• Vapor Pressure: 1.32E-11mmHg at 25°C
• Boiling Point: 524.2°Cat760mmHg
• Flash Point: 270.8°C
• PSA: 51.46000
• Density: 1.271g/cm³
• LogP: 3.58150
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 307.12084340
• Heavy Atom Count: 23
• Complexity: 529

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C=CC2=C(O1)C=C(C3=C2N(C4=CC=CC=C4C3=O)C)O)C
• 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.

Technology Process of Noracronycine

There total 23 articles about Noracronycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

6-Hydroxy-3,3-dimethyl-3,12-dihydro-7H-pyrano<2,3-c>acridin-7-one (13396-93-5) + methyl iodide (74-88-4) → noracronycine (13161-79-0)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.5012/bkcs.2010.31.8.2406

Reference yield: 40.0%

3-chloro-3-methylbut-1-yne (1111-97-3) + 1,3-Dihydroxy-2-iodo-10-methyl-9-acridone (88901-73-9) → 3-(1,1-Dimethyl-2-propinyloxy)-1-hydroxy-10-methyl-9-aridon (28333-10-0) + noracronycine (13161-79-0)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 100 ℃; for 66h;

DOI:10.1002/jlac.198419840105

Reference yield: 36.2%

dimethylacetal of 3-methyl-3-hydroxybutyraldehyde (31525-67-4) + N-methyl-1,3-dihydroxyacridone (28333-02-0) → Isonoracronycine (27221-44-9) + noracronycine (13161-79-0)

Guidance literature:

With pyridine; at 220 ℃; for 4h; regioselective reaction; Microwave irradiation;

DOI:10.1016/j.tetlet.2010.06.058

upstream raw materials:

1,2-dihydronoracronycine

3-chloro-3-methylbut-1-yne

1,3-Dihydroxy-2-iodo-10-methyl-9-acridone

1,3-dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinone (glyocitrine-II)

Downstream raw materials:

1,2-dihydronoracronycine

3,3,12-trimethyl-6-[[(4-methylphenyl)sulfonyl]oxy]-3H,7H-pyrano[2,3-c]acridin-7-one

acronine

3,12-Dihydro-6-acetoxy-3,3,12-trimethyl-7H-pyrano<2,3-c>acridin-7-on

Refernces

• 1、 Grundon, Michael F.,Probst, Wiltrud,Reisch, Johannes. "Natural Product Chemistry, Part 132: Synthesis and Oxidative Cyclisation of 1,3-Dihydroxy-10-methyl-4-(3-methylbut-2-enyl)-9(10H)-acridinone (Glycocitrine-II)". . p. 157 - 163. Retrieved 1990.
• 2、 Beck,Kwok,Booher,Brown,Patterson,Pranc,Rockey,Pohland. "Synthesis of acronycine.". . p. 4706 - 4710. Retrieved 1968.
• 3、 Hari, Galla Sri,Lee, Yong Rok,Wang, Xue,Lyoo, Won Seok,Kim, Sung Hong. "New synthetic routes to acronycine, noracronycine, and their analogues". experimental part. p. 2406 - 2409. Retrieved 2010/11/18.