Ferrugine

CAS# 58471-11-7

Ferrugine

Catalog No. BCN1910----Order now to get a substantial discount!

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Quality Control of Ferrugine

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Chemical structure

Ferrugine

3D structure

Chemical Properties of Ferrugine

Cas No. 58471-11-7 SDF Download SDF
PubChem ID 134715032 Appearance Powder
Formula C15H19NO M.Wt 229.32
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-2-yl]-phenylmethanone
SMILES CN1C2CCC(C1CC2)C(=O)C3=CC=CC=C3
Standard InChIKey FKBXXVPBVMWIDS-HPNRGHHYSA-N
Standard InChI InChI=1S/C15H19NO/c1-16-12-7-9-13(14(16)10-8-12)15(17)11-5-3-2-4-6-11/h2-6,12-14H,7-10H2,1H3/t12-,13?,14-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Protocol of Ferrugine

Structure Identification
Tetrahedron,2012,68(39): 8236–8244.

Approaches to the enantioselective synthesis of ferrugine and its analogues[Reference: WebLink]

A four-step synthetic route, to Ferrugine (2α-benzoyltropane), its methyl analogue (2-acetyltropane) and their N-benzyl analogues is reported.
METHODS AND RESULTS:
The reaction sequence uses tropinone or N-benzylnortropinone aldols as key intermediates. Reduction of aldol derived N-tosylhydrazones and oxidation of the side chain hydroxyl group followed by spontaneous diastereomer equilibration provides the final products. Relative configuration of the exo,anti N-methyl and N-benzyl aldols was retained during N-tosylhydrazone formation. The relative stereochemistry of N-tosylhydrazones was assigned by single crystal diffraction.
CONCLUSIONS:
The final products, Ferrugine and its methyl analogue, were synthesized in enantiomerically pure form via asymmetric deprotonation of tropinone using chiral lithium amide/lithium chloride aggregate prepared in situ from (S,S)-N,N-bis(1-phenylethyl)amine hydrochloride.

Tetrahedron Letters,2009,50(51):7196–7198.

Enantioselective route to ferrugine and its methyl analogue via aldol deoxygenation[Reference: WebLink]

A simple enantioselective approach to Ferrugine (2α-benzoyltropane) and its methyl analogue (2-acetyltropane) is reported.
METHODS AND RESULTS:
The four-step sequence uses an enantioselective aldol reaction of tropinone with benzaldehyde or acetaldehyde, combined with an aldol deoxygenation via tosylhydrazone reduction and oxidation of the side-chain hydroxy group. The final products, Ferrugine and its methyl analogue, are prepared in 35% and 23% overall yields, respectively.
CONCLUSIONS:
Both enantiomers of the products (ee 90–99%) are accessible via the same route using either enantiomer of N,N-bis(1-phenylethyl)amine hydrochloride as the chiral reagent.

Ferrugine Dilution Calculator

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Ferrugine Molarity Calculator

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Preparing Stock Solutions of Ferrugine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.3607 mL 21.8036 mL 43.6072 mL 87.2144 mL 109.018 mL
5 mM 0.8721 mL 4.3607 mL 8.7214 mL 17.4429 mL 21.8036 mL
10 mM 0.4361 mL 2.1804 mL 4.3607 mL 8.7214 mL 10.9018 mL
50 mM 0.0872 mL 0.4361 mL 0.8721 mL 1.7443 mL 2.1804 mL
100 mM 0.0436 mL 0.218 mL 0.4361 mL 0.8721 mL 1.0902 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Ferrugine

Thermal elimination of diethyldithiocarbamates and application in the synthesis of (+/-)-ferrugine.[Pubmed:18785775]

J Org Chem. 2008 Oct 17;73(20):8116-9.

Dithiocarbamate-substituted lactams, prepared through group-transfer cyclization reactions of carbamoyl radicals, undergo a Chugaev-like thermal elimination of the dithiocarbamate group in refluxing diphenyl ether to form alpha,beta- and/or beta,gamma-unsaturated amides, depending on the structure of the starting material. This reaction sequence was used to prepare an unsaturated [3.2.2] bridged bicyclic amide, which was converted in a one-pot procedure to the 8-azabicyclo[3.2.1]octane ring system of the tropane alkaloid Ferrugine by treatment with phenyllithium followed by aqueous sodium hydroxide.

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