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Trachelanthamidine
Trachelanthamidine
ChemFaces products have been cited in many studies from excellent and top scientific journals
Product Name Trachelanthamidine
Price:
CAS No.: 526-64-7
Catalog No.: CFN00279
Molecular Formula: C8H15NO
Molecular Weight: 141.21 g/mol
Purity: >=98%
Type of Compound: Alkaloids
Physical Desc.: Oil
Source: The herbs of Senecio nemorensis L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download: COA    MSDS    SDF
Similar structural: Comparison (Web)  (SDF)
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Related Screening Libraries
Size /Price /Stock 10 mM * 100 uL in DMSO / Inquiry / In-stock
10 mM * 1 mL in DMSO / Inquiry / In-stock
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Biological Activity
Description: Reference standards.
Trachelanthamidine Description
Source: The herbs of Senecio nemorensis L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

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After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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Recently, ChemFaces products have been cited in many studies from excellent and top scientific journals

Cell. 2018 Jan 11;172(1-2):249-261.e12.
doi: 10.1016/j.cell.2017.12.019.
IF=36.216(2019)

PMID: 29328914

Cell Metab. 2020 Mar 3;31(3):534-548.e5.
doi: 10.1016/j.cmet.2020.01.002.
IF=22.415(2019)

PMID: 32004475

Mol Cell. 2017 Nov 16;68(4):673-685.e6.
doi: 10.1016/j.molcel.2017.10.022.
IF=14.548(2019)

PMID: 29149595

ACS Nano. 2018 Apr 24;12(4): 3385-3396.
doi: 10.1021/acsnano.7b08969.
IF=13.903(2019)

PMID: 29553709

Nature Plants. 2016 Dec 22;3: 16206.
doi: 10.1038/nplants.2016.205.
IF=13.297(2019)

PMID: 28005066

Sci Adv. 2018 Oct 24;4(10): eaat6994.
doi: 10.1126/sciadv.aat6994.
IF=12.804(2019)

PMID: 30417089
Calculate Dilution Ratios(Only for Reference)
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 need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
Protocol
Structure Identification:
Angew Chem Int Ed Engl. 2014 Nov 24;53(48):13196-200.
Organocatalytic asymmetric Mannich cyclization of hydroxylactams with acetals: total syntheses of (-)-epilupinine, (-)-tashiromine, and (-)-trachelanthamidine.[Pubmed: 25264221]

METHODS AND RESULTS:
An asymmetric, organocatalytic, one-pot Mannich cyclization between a hydroxylactam and acetal is described to provide fused, bicyclic alkaloids bearing a bridgehead N atom. Both aliphatic and aromatic substrates were used in this transformation to furnish chiral pyrrolizidinone, indolizidinone, and quinolizidinone derivatives in up to 89% yield and 97% ee.
CONCLUSIONS:
The total syntheses of (-)-epilupinine, (-)-tashiromine, and (-)-Trachelanthamidine also achieved to demonstrate the generality of the process.
J Org Chem. 2010 Jun 4;75(11):3578-86.
Asymmetric synthesis of 2-alkyl-substituted 2,5-dihydropyrroles from optically active aza-Baylis-Hillman adducts. Formal synthesis of (-)-trachelanthamidine.[Pubmed: 20465267]
A series of optically active 2-alkyl-substituted 2,5-dihydropyrroles were prepared via the asymmetric aza-Baylis-Hillman equivalent reaction and subsequent ring-closure metathesis reaction.
METHODS AND RESULTS:
Optically active aza-Baylis-Hillman adducts underwent a smooth two-step conversion to N-allyl-beta-amino-alpha-methylene esters in high yield, which gave chiral 2,5-dihydropyrroles, potential precursors for the aza-heterocyclic synthesis, almost quantitatively through RCM reaction catalyzed by Grubbs catalyst. The conversion was carried out without loss of the optical purity of the starting material. Synthetic application of the method to (-)-Trachelanthamidine was examined. Hydrogenation of 2,5-dihydropyrrole took place smoothly to give the corresponding 2,3-disubstituted pyrrolidine in good yield. The stereoselectivity of the hydrogenation was sensitive to the presence or absence of the protective group in the C2-side chain. The TBS-protected 2,5-dihydropyrrole gave a 1:1 mixture of the cis/trans isomers, while free alcohol afforded the trans-2,3-disubstituted pyrrolidine in a selectivity of 6:1. The formal synthesis of (-)-Trachelanthamidine was achieved in 11 steps from a chiral sulfinimine.
CONCLUSIONS:
This methodology provided a convenient procedure for the preparation of C2-alkyl-substituted 2,5-dihydropyroles with retention of high optical purity.
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