Lonchocarpin

Base Information

• Chemical Name: Lonchocarpin
• CAS No.: 31501-55-0
• Molecular Formula: C₂₀H₁₈O₃
• Molecular Weight: 306.361
• DSSTox Substance ID: DTXSID60185403
• Nikkaji Number: J18.986C,J3.547.664D
• Wikidata: Q76324023
• Metabolomics Workbench ID: 26489
• ChEMBL ID: CHEMBL457644
• Mol file: 31501-55-0.mol

Synonyms:1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-phenylprop-2-en-1-one;lonchocarpine

Chemical Property of Lonchocarpin

Chemical Property:

• PSA: 46.53000
• LogP: 4.47250
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 306.125594432
• Heavy Atom Count: 23
• Complexity: 485

Purity/Quality:

95%+ or 98%+ ^*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=CC(=C2O)C(=O)C=CC3=CC=CC=C3)C
• Isomeric SMILES: CC1(C=CC2=C(O1)C=CC(=C2O)C(=O)/C=C/C3=CC=CC=C3)C

Technology Process of Lonchocarpin

There total 13 articles about Lonchocarpin 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: 98.0%

6-acetyl-5-hydroxy-2,2-dimethylchromene (24672-84-2) + benzaldehyde (100-52-7) → lonchocarpin (31501-55-0,51589-66-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1055/s-2006-926294

Reference yield: 91.0%

2,4-Dihydroxy-3-C-prenylacetophenone (19825-40-2) + benzaldehyde (100-52-7) → lonchocarpin (31501-55-0,51589-66-3)

Guidance literature:

2,4-Dihydroxy-3-C-prenylacetophenone; With selenium bromide polystyrene resin; In dichloromethane; at 0 - 25 ℃; for 0.5h;

benzaldehyde; With sodium methylate; In tetrahydrofuran; methanol; at 25 ℃; for 72h;

With dihydrogen peroxide; In tetrahydrofuran; at 25 ℃; for 0.5h;

DOI:10.1002/(SICI)1521-3773(20000218)39:4<734::AID-ANIE734>3.0.CO;2-I

Reference yield: 57.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + 5-hydroxy-2,2-dimethyl-2H-chromene-6-carbaldehyde (54287-99-9) → lonchocarpin (31501-55-0,51589-66-3)

Guidance literature:

With 1,2,3,4-tetraphenylcyclopentadiene; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In 1,2-dichloro-ethane; at 120 ℃; for 18h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201203224

upstream raw materials:

6-acetyl-5-hydroxy-2,2-dimethylchromene

benzaldehyde

2,4-Dihydroxy-3-C-prenylacetophenone

5-hydroxy-2,2-dimethyl-2H-chromene-6-carboxylic acid ethyl ester

Downstream raw materials:

1-(5-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-3-phenylpropan-1-one