• Name

  L-KAWAIN

• EINECS 207-907-2
• CAS No. 500-64-1
• Article Data25
• CAS DataBase
• Density 1.15 g/cm³
• Solubility
• Melting Point 142-148℃
• Formula C14H14 O3
• Boiling Point 432.6 °C at 760 mmHg
• Molecular Weight 230.263
• Flash Point 184.6 °C
• Transport Information
• Appearance white, fine powder
• Safety Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.
• Risk Codes 22
• Molecular Structure
• Hazard Symbols Xn
• Synonyms 2H-Pyran-2-one,5,6-dihydro-4-methoxy-6-(2-phenylethenyl)-, [R-(E)]-; 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-styryl-,(R)- (8CI); (+)-Kavain; (+)-Kawain; (R)-(+)-Kavain; Gonosan; Kavain; Kawain;NSC 112162; d-Kawain
• PSA 35.53000
• LogP 2.54560

Synthetic route

77-78-1

dimethyl sulfate

735287-46-4

ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate

500-64-1

Kavain

Conditions

Conditions	Yield
Stage #1: ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate With potassium carbonate In methanol at 20℃; for 2h; Stage #2: dimethyl sulfate In acetone at 20℃;	87%
Stage #1: ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate With potassium carbonate In methanol for 2h; Stage #2: dimethyl sulfate In acetone for 12h;	75%

356793-34-5

(E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

77-78-1

dimethyl sulfate

500-64-1

Kavain

Conditions

Conditions	Yield
Stage #1: (E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester With potassium carbonate In methanol at 20℃; for 5h; Stage #2: dimethyl sulfate In acetone at 20℃; for 12h;	81%

591-50-4

iodobenzene

(R)-6-((E)-2-(tributylstannyl)vinyl)-5,6-dihydro-4-methoxypyran-2-one

500-64-1

Kavain

Conditions

Conditions	Yield
With trifuran-2-yl-phosphane; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran at 50℃; Stille coupling;	75%

77-78-1

dimethyl sulfate

173654-23-4

(R)-6-((E)-Styryl)-dihydro-pyran-2,4-dione

500-64-1

Kavain

Conditions

Conditions	Yield
In acetone at 20℃; for 10h;
In acetone at 20℃; for 15h;

917251-14-0

5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-7-phenyl-hept-6-enoic acid ethyl ester

500-64-1

Kavain

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 85 percent / TBAF / tetrahydrofuran / 2 h 2.1: K2CO3 / methanol / 2 h 2.2: 75 percent / acetone / 12 h View Scheme

356793-34-5

(E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester

500-64-1

Kavain

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 0.17 h / microwave irradiation 2: acetone / 15 h / 20 °C View Scheme

931094-47-2

(E)-(R)-3-Oxo-7-phenyl-5-trimethylsilanyloxy-hept-6-enoic acid methyl ester

500-64-1

Kavain

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: TFA / -78 °C 2: potassium carbonate / methanol / 0.17 h / microwave irradiation 3: acetone / 15 h / 20 °C View Scheme

14371-10-9

(E)-3-phenylpropenal

87830-18-0

ethyl (E)-4-bromo-3-methoxy-2-butenoate

500-64-1

Kavain

Conditions

Conditions	Yield
In benzene

C7H8O4

7417-81-4, 20246-02-0, 73610-10-3, 210539-77-8, 833-82-9

benzyl phenyl sulfoxide

500-64-1

Kavain

Conditions

Conditions	Yield
Multistep reaction.;	100 mg

Brassard's diene

104-55-2

3-phenyl-propenal

A

500-64-1

Kavain

B

188643-55-2

(S)-(-)-kavain

Conditions

Conditions	Yield
With titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; 4-picolylchloride hydrochloride In toluene at 28℃; for 85h; Diels-Alder reaction; optical yield given as %ee; enantioselective reaction;

...Expand

DL-Kavain Chemical Properties

DL-Kavain Toxicity Data With Reference

DL-Kavain Safety Profile

DL-Kavain Specification