Laburnine

CAS# 3348-73-0

Laburnine

2D Structure

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3D structure

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Laburnine

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Chemical Properties of Laburnine

Cas No. 3348-73-0 SDF Download SDF
PubChem ID 94259 Appearance Oil
Formula C8H15NO M.Wt 141.21
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1S,8R)-2,3,5,6,7,8-hexahydro-1H-pyrrolizin-1-yl]methanol
SMILES C1CC2C(CCN2C1)CO
Standard InChIKey LOFDEIYZIAVXHE-HTQZYQBOSA-N
Standard InChI InChI=1S/C8H15NO/c10-6-7-3-5-9-4-1-2-8(7)9/h7-8,10H,1-6H2/t7-,8-/m1/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 Laburnine

Structure Identification
J Org Chem. 1999 Apr 30;64(9):3122-3131.

Enamino Ester Reduction: A Short Enantioselective Route to Pyrrolizidine and Indolizidine Alkaloids. Synthesis of (+)-Laburnine, (+)-Tashiromine, and (-)-Isoretronecanol.[Pubmed: 11674411]


METHODS AND RESULTS:
The scope of these reductions has been extended to the synthesis of three pyrrolizidine or indolizidine alkaloids: (+)-tashiromine, (+)-Laburnine, and (-)-isoretronecanol.
CONCLUSIONS:
Syntheses of these natural products, starting from chiral beta-enamino diesters, were achieved in a short and convenient manner, leading to enantiopure compounds in good overall yields.

Laburnine Dilution Calculator

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Laburnine Molarity Calculator

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Preparing Stock Solutions of Laburnine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 7.0817 mL 35.4083 mL 70.8165 mL 141.633 mL 177.0413 mL
5 mM 1.4163 mL 7.0817 mL 14.1633 mL 28.3266 mL 35.4083 mL
10 mM 0.7082 mL 3.5408 mL 7.0817 mL 14.1633 mL 17.7041 mL
50 mM 0.1416 mL 0.7082 mL 1.4163 mL 2.8327 mL 3.5408 mL
100 mM 0.0708 mL 0.3541 mL 0.7082 mL 1.4163 mL 1.7704 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 Laburnine

Enamino Ester Reduction: A Short Enantioselective Route to Pyrrolizidine and Indolizidine Alkaloids. Synthesis of (+)-Laburnine, (+)-Tashiromine, and (-)-Isoretronecanol.[Pubmed:11674411]

J Org Chem. 1999 Apr 30;64(9):3122-3131.

Various chiral pyrrolidine tetrasubstituted beta-enamino esters were reduced catalytically or chemically with good to moderate diastereoselectivity owing to a chiral induction originated from (S)-alpha-methylbenzylamine. With endocyclic double bond compounds, the best result was obtained using PtO(2) as hydrogenation catalyst and led to a major syn addition product (e.d. 90%). In the case of exocyclic double bond compounds, hydrogenation over Pd/C gave rise to the higher diastereoselectivity and mainly afforded the unexpected anti addition product (e.d. 84%). The scope of these reductions has been extended to the synthesis of three pyrrolizidine or indolizidine alkaloids: (+)-tashiromine, (+)-Laburnine, and (-)-isoretronecanol. Syntheses of these natural products, starting from chiral beta-enamino diesters, were achieved in a short and convenient manner, leading to enantiopure compounds in good overall yields.

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