Arnottianamide
Basic information
- CAS
60394-88-9- Standard SMILES
COc1ccc(-c2ccc3cc4c(cc3c2N(C)C=O)OCO4)c(O)c1OC- InChIKey
WWWKIQOQQGESSQ-UHFFFAOYSA-N- Molecular formula
- C21H19NO6
- Average molar mass
- 381.4 g/mol
- Monoisotopic mass
- 381.12123733
Names & identifiers
- Preferred name
- Arnottianamide
- IUPAC
- N-[6-(2-hydroxy-3,4-dimethoxyphenyl)benzo[f][1,3]benzodioxol-5-yl]-N-methylformamide
- English name
- N-[6-(2-Hydroxy-3,4-dimethoxy phenyl)naphtho[2,3-d][1,3]dioxol-5-yl]-N-methylformamide
- Molecular formula
- C21H19NO6
- Molecular weight
- 381.38
Names & synonyms
ArnottianamideFormamide, N-(6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho(2,3-d)-1,3-dioxol-5-yl)-N-methyl-N-[6-(2-hydroxy-3,4-dimethoxyphenyl)benzo[f][1,3]benzodioxol-5-yl]-N-methylformamideDTXSID30209145N-(6-(2-hydroxy-3,4-dimethoxyphenyl)benzo(f)(1,3)benzodioxol-5-yl)-N-methylformamideRefChem:114148DTXCID5013163660394-88-9N-[6-(2-Hydroxy-3,4-dimethoxy phenyl)naphtho[2,3-d][1,3]dioxol-5-yl]-N-methylformamideN-[6-(2-Hydroxy-3,4-dimethoxy-phenyl)-naphtho[2,3-d][1,3]dioxol-5-yl]-N-methyl-formamideN-[6-(2-hydroxy-3,4-dimethoxyphenyl)-2H-naphtho[2,3-d][1,3]dioxol-5-yl]-N-methylformamideDB-298682
Show more names
Formamide, N-[6-(2-hydroxy-3,4-dimethoxyphenyl)naphtho[2,3-d]-1,3-dioxol-5-yl]-N-methyl-N-[6-(2-HYDROXY-3,4-DIMETHOXY-PHENYL)-NAPHTHO[2,3-'D][1,3]DIOXOL-5-YL]-N-METHYL-FORMAMIDE
N-[6-(2-hydroxy-3,4-dimethoxy phenyl)naphtho[2,3-d][1,3]dioxol-5-yl ]-N-methylformamide
Database identifiers
- CAS
60394-88-9- PubChem CID
- 3085181
- DTXSID
DTXSID30209145- Nikkaji
- J17.916G
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 77.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 547
Physicochemical properties
- Melting point
- 264 · 264-267 °C
- Boiling point
- 573.8 · 573.8±50.0 °C(Predicted)
- Density
- 1.353 · 1.353±0.06 g/cm3(Predicted)
- pka
- 8.5 · 8.50±0.40(Predicted)
Chemistry & industry
Applications
DescriptionArnottianamide occurs in Xanthoxylum arnottianum and, in trace amounts, in X. cuspidatum. It crystallizes as colourless prisms from EtOH and gives an ultraviolet spectrum in ethanol with absorption maxima at 236 and 332 nm and shoulders at 280 and 324 nm. The structure has been elucidated from chemical and spectro-scopic data and confirmed by its preparation from chelerythrine chloride by a Baeyer-Villiger type oxidation of the irnmonium group. Treatment with LiA1H4 gives the deoxo derivative as colourless prisms, m.p. 200-2°C, forming a crystalline methyl derivative, m.p. l66.5-168.5°C.
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