VASICINONE

Base Information

• Chemical Name: VASICINONE
• CAS No.: 486-64-6
• Molecular Formula: C11H10 N2 O2
• Molecular Weight: 202.213
• European Community (EC) Number: 683-100-2
• UNII: G6T5819NXM
• DSSTox Substance ID: DTXSID80964090
• Nikkaji Number: J783.610D
• Wikipedia: Vasicinone
• Wikidata: Q15427947
• Metabolomics Workbench ID: 69533
• ChEMBL ID: CHEMBL3120244
• Mol file: 486-64-6.mol

Synonyms:Pyrrolo[2,1-b]quinazolin-9(1H)-one,2,3-dihydro-3-hydroxy-, (S)- (8CI); Vasicinone (6CI,7CI); (-)-Vasicinone;l-Vasicinone

Chemical Property of VASICINONE

Chemical Property:

• Vapor Pressure: 1.88E-07mmHg at 25°C
• Melting Point: 200-202oC
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 409.8°Cat760mmHg
• PKA: 12.76±0.20(Predicted)
• Flash Point: 201.7°C
• PSA: 55.12000
• Density: 1.5g/cm³
• LogP: 0.83360
• Water Solubility.: 1.597g/L(25 oC)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 202.074227566
• Heavy Atom Count: 15
• Complexity: 327

Purity/Quality:

99%, ^*data from raw suppliers

Vasicinone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2C(=NC3=CC=CC=C3C2=O)C1O
• Isomeric SMILES: C1CN2C(=NC3=CC=CC=C3C2=O)[C@H]1O
• Description: A further alkaloid present in Adhatoda vasica and Peganum harmala, this base forms colourless crystals from 95 per cent EtOH. It has [α]22D - 100° (c 0.5, CHCL3) and the ultraviolet spectrum has absorption maxima at 227, 272, 302 and 315 mfJ.. The alkaloid yields a series of crystalline salts with mineral acids, e.g. the hydrochloride, m.p. 232-4°C; hydro bromide, m.p. 254-5°C (dec.); hydriodide, m.p. 222-6°C (dec.); nitrate, m.p. 138-9° C (dec.) and the sulphate, m.p. l82-5°C (dec.). The optically inactive form of the base has been prepared synthetically, m.p. 211- 2°C. The alkaloid is an active bronchodilator.

Technology Process of VASICINONE

There total 20 articles about VASICINONE 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: 90.0%

1-[1(S),3-dihydroxypropyl]quinazolin-4(1H)-one (391249-56-2) → (S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one (486-64-6)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo010727l

Reference yield: 84.0%

O-tert-butydimethylsilylvasicinone (182058-08-8) → (S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one (486-64-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 15h;

DOI:10.1002/adsc.201300950

Reference yield: 57.0%

deoxyvasicinone (530-53-0) → (S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one (486-64-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/j.tet.2009.01.077

upstream raw materials:

deoxyvasicinone

O-tert-butydimethylsilylvasicinone

vinyl acetate

(+/-)-vasicinone

Refernces

• 1、 Afanasyev, Oleg I.,Podyacheva, Evgeniya,Rudenko, Alexander,Tsygankov, Alexey A.,Makarova, Maria,Chusov, Denis. "Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family". . p. 9347 - 9360. Retrieved 2020/08/14.
• 2、 Aga, Mushtaq A.,Kumar, Brijesh,Rouf, Abdul,Shah, Bhahwal A.,Andotra, Samar S.,Taneja, Subhash C.. "Natural (-)-vasicine as a novel source of optically pure 1-benzylpyrrolidin-3-ol". . p. 969 - 977. Retrieved 2013/06/27.