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4-methoxy-6-vinyl-2H-pyran-2-one
4-methoxybenzenediazonium tetrafluoroborate
yangonin
Conditions | Yield |
---|---|
Stage #1: 4-methoxy-6-vinyl-2H-pyran-2-one With sodium acetate; palladium diacetate In acetonitrile for 0.166667h; Heck-Matsuda reaction; Stage #2: 4-methoxybenzenediazonium tetrafluoroborate In acetonitrile Heck-Matsuda reaction; | 96% |
(4-Methoxy-2-oxo-2H-pyran-6-yl)methyltriphenylphosphonium Bromide
4-methoxy-benzaldehyde
yangonin
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol; N,N-dimethyl-formamide for 16h; Ambient temperature; | 95% |
(E)-4-methoxy-6-(4-methoxystyryl)-5,6-dihydro-2H-pyran-2-one
yangonin
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 2h; Inert atmosphere; Reflux; | 85% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 2h; Inert atmosphere; Reflux; | 85% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 2h; Reflux; | 80% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran for 0.5h; Reflux; | 303.5 mg |
Conditions | Yield |
---|---|
With triisopropylamine In dichloromethane at -78 - 20℃; for 2h; | 65% |
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 25℃; for 48h; Aldol Condensation; | 61% |
With magnesium methanolate Inert atmosphere; Reflux; | 59% |
With magnesium In methanol for 4h; Reflux; | 30% |
diazomethane
6-(4-methoxy-trans-styryl)-pyran-2,4-dione
A
2-methoxy-6-<2-(4-methoxyphenyl)ethenyl>pyran-4-one
B
yangonin
Conditions | Yield |
---|---|
With diethyl ether |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 18h; Ambient temperature; Yield given; |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) COCl2, 2.) triethylamine / 1.) RT, 18 h, 2.) petroleum ether, CH2Cl2, 0 deg C, 30 min 2: 53 percent / 60 percent NaH, 1.46 M n-BuLi / tetrahydrofuran; hexane / 20 min, rt; 0 deg C, 10 min; 0 deg C, 1-2 h 3: 1.) TFA, 2.) acetic anhydride / 1.) CH2Cl2, rt, 1 h, 2.) rt, 18 h 4: K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 53 percent / 60 percent NaH, 1.46 M n-BuLi / tetrahydrofuran; hexane / 20 min, rt; 0 deg C, 10 min; 0 deg C, 1-2 h 2: 1.) TFA, 2.) acetic anhydride / 1.) CH2Cl2, rt, 1 h, 2.) rt, 18 h 3: K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme |
(E)-tert-butyl 3,5-dioxo-7-(p-methoxyphenyl)hept-6-enoate
yangonin
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) TFA, 2.) acetic anhydride / 1.) CH2Cl2, rt, 1 h, 2.) rt, 18 h 2: K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme |
The Yangonin, with the CAS registry number 500-62-9, has the systematic name of 4-methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]-2H-pyran-2-one. And the molecular formula of the chemical is C15H14O4.
The characteristics of this chemical are as followings: (1)ACD/LogP: 1.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.74; (4)ACD/LogD (pH 7.4): 1.74; (5)ACD/BCF (pH 5.5): 12.48; (6)ACD/BCF (pH 7.4): 12.48; (7)ACD/KOC (pH 5.5): 211.96; (8)ACD/KOC (pH 7.4): 211.96; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 44.76 Å2; (13)Index of Refraction: 1.577; (14)Molar Refractivity: 70.99 cm3; (15)Molar Volume: 213.9 cm3; (16)Polarizability: 28.14×10-24cm3; (17)Surface Tension: 45.1 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 219.8 °C; (20)Enthalpy of Vaporization: 75.35 kJ/mol; (21)Boiling Point: 487.6 °C at 760 mmHg; (22)Vapour Pressure: 1.18E-09 mmHg at 25°C.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C/1O\C(=CC(\OC)=C\1)\C=C\c2ccc(OC)cc2
(2)InChI: InChI=1/C15H14O4/c1-17-12-6-3-11(4-7-12)5-8-13-9-14(18-2)10-15(16)19-13/h3-10H,1-2H3/b8-5+
(3)InChIKey: XLHIYUYCSMZCCC-VMPITWQZBG
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 1500mg/kg (1500mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969. | |
mouse | LD50 | intravenous | 41mg/kg (41mg/kg) | BEHAVIORAL: ANTICONVULSANT | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969. |
mouse | LD50 | oral | > 1500mg/kg (1500mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 177, Pg. 261, 1969. |