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CAS No.: | 500-64-1 |
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Name: | L-KAWAIN |
Article Data: | 25 |
Molecular Structure: | |
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 |
Conditions | Yield |
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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% |
(E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester
dimethyl sulfate
Kavain
Conditions | Yield |
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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% |
Conditions | Yield |
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With trifuran-2-yl-phosphane; tris(dibenzylideneacetone)dipalladium (0) In tetrahydrofuran at 50℃; Stille coupling; | 75% |
Conditions | Yield |
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In acetone at 20℃; for 10h; | |
In acetone at 20℃; for 15h; |
5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-7-phenyl-hept-6-enoic acid ethyl ester
Kavain
Conditions | Yield |
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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 |
(E)-(R)-5-Hydroxy-3-oxo-7-phenyl-hept-6-enoic acid methyl ester
Kavain
Conditions | Yield |
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Multi-step reaction with 2 steps 1: potassium carbonate / methanol / 0.17 h / microwave irradiation 2: acetone / 15 h / 20 °C View Scheme |
(E)-(R)-3-Oxo-7-phenyl-5-trimethylsilanyloxy-hept-6-enoic acid methyl ester
Kavain
Conditions | Yield |
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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 |
Conditions | Yield |
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In benzene |
Conditions | Yield |
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Multistep reaction.; | 100 mg |
Conditions | Yield |
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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; |
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
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. |
Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.
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 .