2-Azetidinone, 1-(20-alpha-(dimethylamino)-4-oxo-5-alpha-pregnan-3-beta-yl)-3-isopropyl-, (3R)-
Basic information
- CAS
6156-99-6- Standard SMILES
CC(C)[C@@H]1CN([C@H]2CC[C@@]3(C)[C@@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@H](C(C)N(C)C)CC[C@@H]43)C2=O)C1=O- InChIKey
MHFGHEARXPBTQH-PTKYFECBSA-N- Molecular formula
- C29H48N2O2
- Average molar mass
- 456.7 g/mol
- Monoisotopic mass
- 456.37157878
Overview
2-Azetidinone, 1-(20-alpha-(dimethylamino)-4-oxo-5-alpha-pregnan-3-beta-yl)-3-isopropyl-, (3R)- has been reported in Pachysandra terminalis with data available.
Names & identifiers
- Preferred name
- 2-Azetidinone, 1-(20-alpha-(dimethylamino)-4-oxo-5-alpha-pregnan-3-beta-yl)-3-isopropyl-, (3R)-
- IUPAC
- (3R)-1-[(3S,5R,8S,9S,10R,13S,14S,17R)-17-[1-(dimethylamino)ethyl]-10,13-dimethyl-4-oxo-1,2,3,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]-3-propan-2-ylazetidin-2-one
- English name
- (3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one
- Molecular formula
- C29H48N2O2
- Molecular weight
- 456.72
Names & synonyms
2-Azetidinone, 1-(20-alpha-(dimethylamino)-4-oxo-5-alpha-pregnan-3-beta-yl)-3-isopropyl-, (3R)-(3R)-1-[(3S,5R,8S,9S,10R,13S,14S,17R)-17-[1-(dimethylamino)ethyl]-10,13-dimethyl-4-oxo-1,2,3,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]-3-propan-2-ylazetidin-2-one(3R)-1-((3S,5R,8S,9S,10R,13S,14S,17R)-17-(1-(dimethylamino)ethyl)-10,13-dimethyl-4-oxo-1,2,3,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta(a)phenanthren-3-yl)-3-propan-2-ylazetidin-2-oneRefChem:1062284Pachystermine A6156-99-6DTXSID00977142NS0009428320-(Dimethylamino)-3-[2-oxo-3-(propan-2-yl)azetidin-1-yl]pregnan-4-one20-(Dimethylamino)-3beta-[(3R)-2-oxo-3-(propan-2-yl)azetidin-1-yl]-5alpha,17alpha-pregnan-4-one20α-dimethylamino-3β-(3'-isopropylidene)-lactam-5α-pregn-4-one(3R)-1-[(20S)-20-(Dimethylamino)-4-oxo-5α-pregnan-3β-yl]-3-isopropylazetidin-2-one
Show more names
2-Azetidinone, 1-[(3β,5α,20S)-20-(dimethylamino)-4-oxopregnan-3-yl]-3-(1-methylethyl)-, (3R)-
Properties
Computed structural properties
- XLogP
- 6.1
- Topological polar surface area
- 40.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 33
- Formal charge
- 0
- Complexity
- 807
Physicochemical properties
- Melting point
- 220 · 220-4°C
- Boiling point
- 560.7 · 560.7±25.0 °C(Predicted)
- Density
- 1.06 · 1.060±0.06 g/cm3(Predicted)
- pka
- 9.6 · 9.60±0.50(Predicted)
Chemistry & industry
Applications
DescriptionThis alkaloid is the major base found in Pachysandra terminalis Sieb. et Zucco Like the other alkaloids present in this plant, it contains the pregnane skeleton. It is dextrorotatory with [α]D + 24° (CHCI 3). It has two keto groups in the molecule, one being present in a four-membered ring. Reduction with NaBH4 furnishes Pachystermine B (q.v.). The structure has been confirmed by the partial synthesis of the alkaloid.
Related reactions
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Compound notes
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