Porantherine
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| Category | Others |
| Catalog number | BBF-05254 |
| CAS | 33529-61-2 |
| Molecular Weight | 217.35 |
| Molecular Formula | C15H23N |
| Purity | ≥95% by HPLC |
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Description
It is a polycyclic alkaloid obtained from the shrub Poranthera corymbosa.
Specification
| Related CAS | 108818-56-0 (hydrochloride) 54382-19-3 ((±)-form) |
| Synonyms | (1R,6aS)-3aβ,4,5,6,7,8,9,9a-Octahydro-9aβ-methyl-1H-1,6a-ethanopyrido[2,1,6-de]quinolizine; (1S,4R,7S,9R)-9-Methyl-8-azatetracyclo[5.5.3.01,8.04,9]pentadec-5-ene; (1R,3aS,6aS,9aR)-3a,4,5,6,7,8,9,9a-octahydro-9a-methyl-1H-1,6a-ethanopyrido[2,1,6-de]quinolizine |
| Storage | Store at -20°C |
| IUPAC Name | (1R,4R,7S,9S)-9-methyl-8-azatetracyclo[5.5.3.01,8.04,9]pentadec-5-ene |
| Canonical SMILES | CC12CCCC34N1C(CCC3)C=CC2CC4 |
| InChI | InChI=1S/C15H23N/c1-14-8-3-10-15-9-2-4-13(16(14)15)6-5-12(14)7-11-15/h5-6,12-13H,2-4,7-11H2,1H3/t12-,13-,14-,15+/m0/s1 |
| InChI Key | YXWOUJYNFPKTLH-ZQDZILKHSA-N |
Properties
| Appearance | Solid |
| Boiling Point | 309.6±11.0°C at 760 mmHg |
| Melting Point | 36-40°C |
| Density | 1.1±0.1 g/cm3 |
| Solubility | Soluble in Chloroform, DMSO, Methanol |
Reference Reading
1. Synthetic approaches to racemic porantheridine and 8-epihalosaline via a nitroso Diels-Alder cycloaddition/ring-rearrangement metathesis sequence
Pierre Sancibrao, Delphine Karila, Cyrille Kouklovsky, Guillaume Vincent J Org Chem. 2010 Jun 18;75(12):4333-6. doi: 10.1021/jo100768d.
The application of a sequence involving a nitroso Diels-Alder cycloaddition and a ring-rearrangement metathesis to the total synthesis of (+/-)-8-epihalosaline and the formal synthesis of (+/-)-porantheridine is described. The formation of the 2,6-trans-disubstituted piperidine backbone of porantheridine has been accomplished by addition of a Grignard reagent onto an N-benzylpiperidone followed by a highly diastereoselective reduction of the imminium intermediate in one pot.
2. Stereodivergent synthesis of piperidine alkaloids by ring-rearrangement metathesis/reductive lactam alkylation of nitroso Diels-Alder cycloadducts
Guillaume Vincent, Delphine Karila, Georges Khalil, Pierre Sancibrao, Didier Gori, Cyrille Kouklovsky Chemistry. 2013 Jul 8;19(28):9358-65. doi: 10.1002/chem.201300836. Epub 2013 Jun 5.
A general methodology for the stereoselective synthesis of 2-(2-hydroxyalkyl)piperidine alkaloids by ring-rearrangement metathesis of nitroso Diels-Alder cycloadducts is reported. The approach is illustrated by the formal synthesis of porantheridine and the total synthesis of andrachcinidine through a diastereodivergent allylation of an N-alkoxy bicyclic lactam. The asymmetric synthesis of the latter alkaloid provides new insights into the configurational stability of cycloadducts between chloronitroso reagents and cyclopentadiene.
3. A formal synthesis of porantheridine and an epimer
Roderick W Bates, Yongna Lu J Org Chem. 2009 Dec 18;74(24):9460-5. doi: 10.1021/jo9021925.
A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
