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500-64-1

Basic Information
CAS No.: 500-64-1
Name: L-KAWAIN
Article Data: 25
Molecular Structure:
Molecular Structure of 500-64-1 (L-KAWAIN)
Formula: C14H14 O3
Molecular Weight: 230.263
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
EINECS: 207-907-2
Density: 1.15 g/cm3
Melting Point: 142-148℃
Boiling Point: 432.6 °C at 760 mmHg
Flash Point: 184.6 °C
Appearance: white, fine powder
Hazard Symbols: Xn
Risk Codes: 22
Safety: Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In benzene
Conditions
ConditionsYield
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
ConditionsYield
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;
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Chemistry

Empirical Formula of Kawain (CAS NO.500-64-1): C14H14O3
Molecular Weight: 230.2592 
EINECS: 207-907-2
Index of Refraction: 1.564
Density: 1.15 g/cm3
Flash Point: 184.6 °C
Enthalpy of Vaporization: 68.85 kJ/mol
Boiling Point: 432.6 °C at 760 mmHg
Vapour Pressure: 1.09E-07 mmHg at 25 °C
Structure of Kawain (CAS NO.500-64-1):
               
IUPAC Name of Kawain (CAS NO.500-64-1): (2R)-4-Methoxy-2-[(E)-2-phenylethenyl]-2,3-dihydropyran-6-one
Canonical SMILES: COC1=CC(=O)OC(C1)C=CC2=CC=CC=C2
Isomeric SMILES: COC1=CC(=O)O[C@H](C1)/C=C/C2=CC=CC=C2
InChI: InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1
InChIKey: XEAQIWGXBXCYFX-GUOLPTJISA-N
 

Toxicity Data With Reference

1.    

orl-mus LD50:1130 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 177 (1969),261.
2.    

ipr-mus LD50:420 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 177 (1969),261.
3.    

ivn-mus LD50:69 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 177 (1969),261.

Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.

Specification

 Kawain ,its cas register number is 500-64-1. It also can be called (+)-Kavain ; (R)-5,6-Dihydro-4-methoxy-6-styryl-2H-pyran-2-one ; [R-(E)]-5,6-Dihydro-4-methoxy-6-(2-phenylethenyl)-2H-pyran-2-one and (6R)-4-Methoxy-6-[(E)-2-phenylvinyl]-5,6-dihydro-2H-pyran-2-one .