Products Categories
| CAS No.: | 6559-91-7 |
|---|---|
| Name: | 4'-Demethylepipodophyllotoxin |
| Molecular Structure: | |
|
|
|
| Formula: | C21H20O8 |
| Molecular Weight: | 400.385 |
| Synonyms: | Epipodophyllotoxin,4'-demethyl- (7CI,8CI);Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, [5R-(5a,5ab,8aa,9b)]-;(-)-4'-Demethylepipodophyllotoxin;4'-Demethylepipodophyllotoxin;4'-O-demethylepipodophyllotoxin; |
| EINECS: | 613-823-0 |
| Density: | 1.446 g/cm3 |
| Melting Point: | 246-248 °C |
| Boiling Point: | 626.5 °C at 760 mmHg |
| Flash Point: | 224.4 °C |
| Appearance: | White crystalline powder |
| PSA: | 103.68000 |
| LogP: | 2.10620 |
- 81281-59-67-Benzylideneaminotheophylline
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 68439-39-4Poly(oxy-1,2-ethanediyl), alpha-(2-ethylhexyl)-omega-hydroxy-,
- 852475-26-4MC1568
- 958254-66-51H-Imidazo[4,5-b]pyridine-2-carboxaldehyde, 1-methyl-, hydrochloride
- 99170-93-1N-Methyl-2-oxazolamine
- 717878-06-31-(4-fluorophenyl)-4-nitro-1H-imidazole
- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
| Conditions | Yield |
|---|---|
| With methanesulfonic acid; DL-methionine; trifluoroacetic acid at 40℃; for 0.75h; | 93% |
| Stage #1: podofilox With methanesulfonic acid; sodium iodide In dichloromethane at 0 - 20℃; for 5h; Stage #2: With barium carbonate In water; acetone at 40℃; for 0.5h; | 90% |
| Stage #1: podofilox With 1-(Trimethylsilyl)imidazole In dichloromethane at 0℃; Stage #2: With water; barium carbonate In acetone | 79% |
- 156350-44-6
Carbonic acid benzyl ester 4-((5R,5aR,8aR)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester
- 6559-91-7
4'-demethylepipodophyllotoxin
| Conditions | Yield |
|---|---|
| With ruthenium(II) chloride; (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); hydrogen In isopropyl alcohol at 20 - 25℃; under 38002.6 Torr; for 18h; | 89% |
- 16477-16-0
4'-O-demethyl-4β-bromo-4-desoxypodophyllotoxin
- 6559-91-7
4'-demethylepipodophyllotoxin
| Conditions | Yield |
|---|---|
| With water; barium carbonate In acetone at 40℃; for 4h; | 71% |
| With barium carbonate In water; acetone for 1h; Heating; | 52% |
- 64-19-7
acetic acid
- 518-28-5
podofilox
A
- 6559-91-7
4'-demethylepipodophyllotoxin
B
- 102306-96-7
4'-demethyl-β-apopicropodophyllotoxin
C
- 102306-95-6
4'-demethyl-1-O-ethyl-1-epipodophyllotoxin
D
- 4375-07-9
epipodophyllotoxin
| Conditions | Yield |
|---|---|
| With hydrogen bromide 1.) 15 min, 2.) RT, 20 h; Multistep reaction. Further byproducts given; |
- 64-19-7
acetic acid
- 518-28-5
podofilox
A
- 6559-91-7
4'-demethylepipodophyllotoxin
B
- 102306-96-7
4'-demethyl-β-apopicropodophyllotoxin
C
- 102306-97-8
3',4'-didemethylepipodophyllotoxin
D
- 4375-07-9
epipodophyllotoxin
| Conditions | Yield |
|---|---|
| With hydrogen bromide 1.) 15 min, 2.) RT, 20 h; Multistep reaction. Further byproducts given; |
- 33419-42-0
etoposide
- 6559-91-7
4'-demethylepipodophyllotoxin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: sodium iodide; chloro-trimethyl-silane / acetonitrile / 0 °C 2: water; barium carbonate / acetone / 20 °C View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1.1: sodium hydroxide / tetrahydrofuran / 25 - 30 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -20 - -15 °C / Inert atmosphere 3.1: iron(III) chloride / dichloromethane / 1 h / 18 - 22 °C 4.1: triethylamine / dichloromethane / 1 h / -2 - 2 °C 5.1: palladium diacetate; triphenylphosphine; potassium carbonate / acetonitrile / 20 h / 75 - 85 °C 6.1: pyridine; ozone / dichloromethane; methanol / 5 h / -25 - -15 °C 6.2: 4 h / 20 °C / Inert atmosphere 7.1: (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); ruthenium(II) chloride; hydrogen / isopropyl alcohol / 18 h / 20 - 25 °C / 38002.6 Torr View Scheme |
- 6559-91-7
4'-demethylepipodophyllotoxin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 3 h / -20 - -15 °C / Inert atmosphere 2.1: iron(III) chloride / dichloromethane / 1 h / 18 - 22 °C 3.1: triethylamine / dichloromethane / 1 h / -2 - 2 °C 4.1: palladium diacetate; triphenylphosphine; potassium carbonate / acetonitrile / 20 h / 75 - 85 °C 5.1: pyridine; ozone / dichloromethane; methanol / 5 h / -25 - -15 °C 5.2: 4 h / 20 °C / Inert atmosphere 6.1: (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); ruthenium(II) chloride; hydrogen / isopropyl alcohol / 18 h / 20 - 25 °C / 38002.6 Torr View Scheme |
- 6559-91-7
4'-demethylepipodophyllotoxin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1.1: iron(III) chloride / dichloromethane / 1 h / 18 - 22 °C 2.1: triethylamine / dichloromethane / 1 h / -2 - 2 °C 3.1: palladium diacetate; triphenylphosphine; potassium carbonate / acetonitrile / 20 h / 75 - 85 °C 4.1: pyridine; ozone / dichloromethane; methanol / 5 h / -25 - -15 °C 4.2: 4 h / 20 °C / Inert atmosphere 5.1: (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); ruthenium(II) chloride; hydrogen / isopropyl alcohol / 18 h / 20 - 25 °C / 38002.6 Torr View Scheme |
- 6559-91-7
4'-demethylepipodophyllotoxin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 1 h / -2 - 2 °C 2.1: palladium diacetate; triphenylphosphine; potassium carbonate / acetonitrile / 20 h / 75 - 85 °C 3.1: pyridine; ozone / dichloromethane; methanol / 5 h / -25 - -15 °C 3.2: 4 h / 20 °C / Inert atmosphere 4.1: (S)-N2,N2'-bis(pyridin-2-ylmethyl-1,1'-binaphthyl-2,2'-diamine); ruthenium(II) chloride; hydrogen / isopropyl alcohol / 18 h / 20 - 25 °C / 38002.6 Torr View Scheme |
What can I do for you?
Get Best Price
Specification
The CAS registry number of 4'-Demethylepipodophyllotoxin is 6559-91-7. The IUPAC name is (5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one. It belongs to the classes of Miscellaneous Natural Products; Plant Oils, Toxins, Phenolic Acids & Derivatives; Inhibitors. In addition, its molecular formula is C21H20O8 and the molecular weight is 400.38. Besides, it is off-white solid. And it can be used as a potent inhibitor of microtubule assembly.
Physical properties about this chemical are: (1)ACD/LogP: 0.71; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.71; (4)ACD/LogD (pH 7.4): 0.71; (5)ACD/BCF (pH 5.5): 2.05; (6)ACD/BCF (pH 7.4): 2.04; (7)ACD/KOC (pH 5.5): 58.17; (8)ACD/KOC (pH 7.4): 58; (9)H bond acceptors: 8; (10)H bond donors: 2; (11)Freely Rotating Bonds: 5; (12)Polar Surface Area: 81.68 Å2; (13)Index of Refraction: 1.637; (14)Molar Refractivity: 99.48 cm3; (15)Molar Volume: 276.8 cm3; (16)Polarizability: 39.43×10-24cm3; (17)Surface Tension: 60.3 dyne/cm; (18)Density: 1.446 g/cm3; (19)Flash Point: 224.4 °C; (20)Enthalpy of Vaporization: 97.48 kJ/mol; (21)Boiling Point: 626.5 °C at 760 mmHg; (22)Vapour Pressure: 1.46E-16 mmHg at 25 °C.
Preparation of 4'-Demethylepipodophyllotoxin: it can be prepared by 1-Brom-1-desoxy-4'-demethyl-epipodophyllotoxin. This reaction will need reagents BaCO3 and H2O and solvent acetone. The reaction time is 4 hours at reaction temperature of 40 °C. The yield is about 71%.
Uses of 4'-Demethylepipodophyllotoxin: it can be used to get 2'-chloro-4'-O-demethylepipodophyllotoxin. This reaction will need reagent N-chlorosuccinimide and solvent dimethylformamide. The reaction time is 3.5 hours at ambient temperature. The yield is about 75%.
People can use the following data to convert to the molecule structure.
(1)SMILES: O=C4OC[C@@H]5[C@H](O)c2cc1OCOc1cc2[C@@H](c3cc(OC)c(O)c(OC)c3)[C@@H]45
(2)InChI: InChI=1/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1
(3)InChIKey: YVCVYCSAAZQOJI-JHQYFNNDBA