Dihydrokawain

Base Information

• Chemical Name: Dihydrokawain
• CAS No.: 587-63-3
• Deprecated CAS: 19451-52-6,19902-90-0,24576-85-0
• Molecular Formula: C14H16 O3
• Molecular Weight: 232.279
• NSC Number: 112163
• UNII: NW8ZGW9XRZ
• DSSTox Substance ID: DTXSID8033433
• Nikkaji Number: J766.672A
• Wikipedia: Dihydrokavain
• Wikidata: Q27285076
• Metabolomics Workbench ID: 142994
• ChEMBL ID: CHEMBL569329
• Mol file: 587-63-3.mol

Synonyms:dihydrokavain

Chemical Property of Dihydrokawain

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 56-60ºC
• Refractive Index: 1.5557 (estimate)
• Boiling Point: 413.6 ºC at 760 mmHg
• Flash Point: 175.6 ºC
• PSA: 35.53000
• Density: 1.12 g/cm3
• LogP: 2.46500
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 232.109944368
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

more than 98% ^*data from raw suppliers

Dihydrokawain ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=O)OC(C1)CCC2=CC=CC=C2
• Isomeric SMILES: COC1=CC(=O)O[C@H](C1)CCC2=CC=CC=C2
• Uses: (+)-(S)-Dihydrokavain is a kavalactone found in kava beverages consumed by South Pacific islanders. Furthermore, roots and extracts of the kava plant have been used in herbal medicine to treat sleep disturbances, as well as stress and anxiety.

Technology Process of Dihydrokawain

There total 30 articles about Dihydrokawain 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: 86.0%

dimethyl sulfate (77-78-1) + (6S)-6-(2-phenylethyl)dihydropyran-2,4(3)-dione (182950-96-5) → 7,8-dihydrokawain (587-63-3)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 20h;

DOI:10.1002/ejoc.200400833

Reference yield:

methanol (67-56-1) + C13H14O3 → 7,8-dihydrokawain (587-63-3)

Guidance literature:

With sulfuric acid; mercury(II) oxide; at 20 ℃; for 24h;

DOI:10.1080/00397911.2018.1489057

Reference yield:

methyl 3-oxo-5-phenylpentanoate (30414-58-5) → 7,8-dihydrokawain (587-63-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 80 percent / sodium borohydride / methanol / 0 - 20 °C

2.1: 46 percent / lipase PS-C / diisopropyl ether / 18 h

3.1: 90 percent / potassium carbonate / methanol

4.1: lithium diisopropylamide / tetrahydrofuran / -78 °C

4.2: tetrahydrofuran / -78 °C

5.1: TFA / CH₂Cl₂ / 10 h

6.1: potassium carbonate / acetone

With sodium tetrahydroborate; potassium carbonate; trifluoroacetic acid; lithium diisopropyl amide; Lipase PS-C; In tetrahydrofuran; methanol; dichloromethane; di-isopropyl ether; acetone;

DOI:10.1016/j.tetlet.2006.09.155

upstream raw materials:

kawain

dimethyl sulfate

(6S)-6-(2-phenylethyl)dihydropyran-2,4⁽³⁾-dione

5,6-dehydrokawain

Downstream raw materials:

(8S)-hydroxy-(6S)-dihydrokawain

Refernces

• 1、 Mineeva. "Enantioselective synthesis of (+)-(S)-7,8-dihydrokavain and (4R,6R)-4-hydroxy-6-(2-phenylethyl)tetrahydro-2H-pyran-2-one, lactone analog of compactin and mevinolin". . p. 712 - 716. Retrieved 2013/07/11.
• 2、 Paul Raj, I. Victor,Sudalai. "Asymmetric synthesis of (S)-vigabatrin and (S)-dihydrokavain via cobalt catalyzed hydrolytic kinetic resolution of epoxides". . p. 2646 - 2648. Retrieved 2008/09/19.