3-Hydroxy-beta-lapachone

Base Information

• Chemical Name: 3-Hydroxy-beta-lapachone
• CAS No.: 15297-98-0
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.274
• DSSTox Substance ID: DTXSID80934637
• Nikkaji Number: J836.351J
• Wikidata: Q82910554
• ChEMBL ID: CHEMBL264927
• Mol file: 15297-98-0.mol

Synonyms:3-hydroxy-beta-lapachone;3-hydroxylapachone

Chemical Property of 3-Hydroxy-beta-lapachone

Chemical Property:

• Vapor Pressure: 2.28E-08mmHg at 25°C
• Boiling Point: 435.8°C at 760 mmHg
• Flash Point: 166.2°C
• Density: 1.34g/cm³
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 258.08920892
• Heavy Atom Count: 19
• Complexity: 475

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)C3=CC=CC=C3C(=O)C2=O)O)C

Technology Process of 3-Hydroxy-beta-lapachone

There total 16 articles about 3-Hydroxy-beta-lapachone 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: 89.0%

Lapachol (84-79-7) → 3-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (15297-98-0,41019-52-7,41135-46-0) + 2-(1-hydroxy-1-methylethyl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione (82423-03-8,41019-53-8)

Guidance literature:

Lapachol; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.5h;

In dichloromethane; for 1h;

DOI:10.1002/cmdc.201500189

Reference yield: 67.0%

10,11-epoxy-lapachol (195156-48-0) → 3-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (15297-98-0,41019-52-7,41135-46-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃; for 21h;

DOI:10.1016/S0040-4039(98)01880-2

Reference yield: 57.0%

Lapachol (84-79-7) → 2-(1-hydroxy-1-methylethyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (137493-02-8,66512-82-1,41192-67-0) + 3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-naphtho[2,3-b]pyran-5,10-dione (119626-45-8,144125-22-4) + 3-Hydroxy-2,2-dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione (15297-98-0,41019-52-7,41135-46-0) + 2-(1-hydroxy-1-methylethyl)-2,3-dihydronaphtho[1,2-b]furan-4,5-dione (82423-03-8,41019-53-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/jm060849b

upstream raw materials:

dihydroxyhydrolapachol

Lapachol

10,11-epoxy-lapachol

2-hydroxynaphtho-1,4-quinone

Downstream raw materials:

Malonic acid tert-butyl ester 2,2-dimethyl-5,6-dioxo-3,4,5,6-tetrahydro-2H-benzo[h]chromen-3-yl ester

2,2-dimethyl-2H-benzo[g]chromene-5,10-dione

α-lapachone

C₂₈H₂₂N₂O₃