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| CAS No.: | 38462-04-3 |
|---|---|
| Name: | ascofuranone |
| Article Data: | 1 |
| Molecular Structure: | |
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| Formula: | C23H29ClO5 |
| Molecular Weight: | 420.933 |
| Synonyms: | C23H29ClO5;Ascofuranone;Ascofuranon; |
| Density: | 1.207g/cm3 |
| Boiling Point: | 581.2°C at 760 mmHg |
| Flash Point: | 305.3°C |
| Safety: | Moderately toxic by intraperitoneal route. See also ALDEHYDES. When heated to decomposition it emits toxic fumes of Cl−. |
| PSA: | 83.83000 |
| LogP: | 5.22400 |
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- 51759-79-6
(1''S,4''S)-(-)-ascofuranol
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| With pyridinium chlorochromate In dichloromethane for 3h; Ambient temperature; | 22.2% |
- 99529-56-3
(2E,6E,1'S,4'S)-(+)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 9 steps 1: imidazole / dimethylformamide / 6 h / Ambient temperature 2: 92.9 percent / K2CO3 / methanol; H2O / 48 h / Ambient temperature 3: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C 4: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C 5: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature 6: 57 percent / DBU / tetrahydrofuran / 6 h / Heating 7: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min. 8: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 9: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- 99477-55-1, 99529-54-1, 99529-56-3, 99529-57-4
(2E,6E,1'S*,4'S*)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 11 steps 1: 5.14 g / 14 h / 80 °C 2: 76.3 percent / Et3N, HSiCl3 / benzene / 96 h / Ambient temperature 3: imidazole / dimethylformamide / 6 h / Ambient temperature 4: 92.9 percent / K2CO3 / methanol; H2O / 48 h / Ambient temperature 5: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C 6: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C 7: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature 8: 57 percent / DBU / tetrahydrofuran / 6 h / Heating 9: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min. 10: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 11: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- 99477-58-4
(2E,6E,1'S,4'S)-(+)-7-(4'-t-butyldimethylsilyloxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadien-1-ol
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C 2: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C 3: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature 4: 57 percent / DBU / tetrahydrofuran / 6 h / Heating 5: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min. 6: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 7: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- 99477-59-5
(2E,6E,1'S,4'S)-7-(4'-t-butyldimethylsilyloxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl chloride
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C 2: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature 3: 57 percent / DBU / tetrahydrofuran / 6 h / Heating 4: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min. 5: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 6: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- 99477-57-3, 99529-58-5
(2E,6E,1'S,4'S)-(+)-7-(4'-t-butyldimethylsilyloxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1: 92.9 percent / K2CO3 / methanol; H2O / 48 h / Ambient temperature 2: 1.26 g / n-BuLi, Ph3CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C 3: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C 4: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature 5: 57 percent / DBU / tetrahydrofuran / 6 h / Heating 6: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min. 7: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 8: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- 99477-60-8
(2'E,6'E,1''S,4''S)-(+)-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>-2,4-dimethoxy-6-methyl-1,4-cyclohexadiene
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: 50.2 percent / CaCO3, NCS / H2O; dimethylformamide / Ambient temperature 2: 57 percent / DBU / tetrahydrofuran / 6 h / Heating 3: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min. 4: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 5: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- 99477-62-0
(2'E,6'E,1''S,4''S)-4-chloro-2-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>orcinol
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min. 2: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 3: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- 99477-61-9
(2'E,6'E,1''S,4''S)-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: 57 percent / DBU / tetrahydrofuran / 6 h / Heating 2: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min. 3: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 4: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- 99477-63-1
(2'E,6'E,1''S,4''S)-5-chloro-2,4-dihydroxy-6-methyl-3-<7'-(4''-t-butyldimethylsilyloxy-3'',3''-dimethyl-2''-oxacyclopentyl)-3',7'-dimethyl-2',6'-heptadienyl>benzaldehyde
- 38462-04-3
Ascofuranone
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 71 percent / HF / acetonitrile; H2O / 1 h / Ambient temperature 2: 22.2 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme |
- Total:17 Page 1 of 1 1
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Chemistry
IUPAC Name: 5-chloro-3-[(2E,6E)-7-[(2S)-5,5-dimethyl-4-oxooxolan-2-yl]-3-methylocta-2,6-dienyl]-2,4-dihydroxy-6-methylbenzaldehyde
Molecular Weight: 420.92636 g/mol
Molecular Formula: C23H29ClO5
Density: 1.207 g/cm3
Boiling Point: 581.2 °C at 760 mmHg
Flash Point: 305.3 °C
Vapour Pressure: 4.18E-14 mmHg at 25°C
Index of Refraction: 1.577 Molar
Refractivity: 115.63 cm3
Molar Volume: 348.6 cm3
Polarizability: 45.84*10-24cm3
Surface Tension: 47.5 dyne/cm
Enthalpy of Vaporization: 90.13 kJ/mol
XLogP3-AA: 5.5
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 7
Tautomer Count: 50
Exact Mass: 420.170352
MonoIsotopic Mass: 420.170352
Topological Polar Surface Area: 83.8
Heavy Atom Count: 29
Complexity: 668
Defined Atom StereoCenter Count: 1
Isomeric SMILES: CC1=C(C(=C(C(=C1Cl)O)C/C=C(\C)/CC/C=C(\C)/[C@@H]2CC(=O)C(O2)(C)C)O)C=O
InChI: InChI=1S/C23H29ClO5/c1-13(7-6-8-14(2)18-11-19(26)23(4,5)29-18)9-10-16-21(27)17(12-25)15(3)20(24)22(16)28/h8-9,12,18,27-28H,6-7,10-11H2,1-5H3/b13-9+,14-8+/t18-/m0/s1
InChIKey: VGYPZLGWVQQOST-JUERRSSISA-N
Uses
Ascofuranone (CAS NO.38462-04-3) is a lead compound in efforts to produce other drugs targeting this enzyme for the treatment of sleeping sickness. And it is an antibiotic produced by the fungus Ascochyta visiae that inhibits the Trypanosoma brucei alternative oxidase. The compound is effective both in infections in mice and in vitro cell culture. Ascofuranone has also been reported to have anti-tumor activity, and modulate the immune system.
Toxicity Data With Reference
| 1. | ipr-rat LD50:1350 mg/kg | JANTAJ Journal of Antibiotics. 26 (1973),681. | ||
| 2. | ipr-mus LD50:2220 mg/kg | JANTAJ Journal of Antibiotics. 26 (1973),681. |
Safety Profile
Moderately toxic by intraperitoneal route. See also ALDEHYDES. When heated to decomposition it emits toxic fumes of Cl−.
Specification
The Ascofuranone (CAS NO.38462-04-3) is also called 2-Methyl-3-chloro-4,6-dihydroxy-5-[(2E,6E)-3-methyl-7-[(2S)-4-oxo-5,5-dimethyltetrahydrofuran-2-yl]-2,6-octadienyl]benzaldehyde ; 3-Chloro-4,6-dihydroxy-2-methyl-5-[(2E,6E)-3-methyl-7-[(S)-tetrahydro-5,5-dimethyl-4-oxofuran-2-yl]-2,6-octadienyl]benzaldehyde ; Ascofranone ; Ascofuranon . Ascofuranone (CAS NO.38462-04-3) is high toxic. It can produce toxic chloride smoke when buring. So the storage environment should be ventilate, low-temperature and dry.