145199-54-8

Usage

Chemical structure

A cyclic compound with a 1,5,9-triazacyclotridecane core and a 3-hydroxy-9-[(2E)-1-oxo-3-phenyl-2-propenyl]-2-phenyl group attached to it.

Functional groups

Contains a hydroxy group (-OH) and a phenyl group (C6H5-).

Stereoisomer configuration

(2R,3S), indicating the specific arrangement of atoms in the molecule.

Derivative

It is a derivative of 1,5,9-triazacyclotridecane, a nitrogen-containing cyclic compound.

Chemical and pharmaceutical applications

Used in various chemical and pharmaceutical applications, potentially as a building block for the synthesis of more complex molecules.

Potential uses

Due to its unique structure and functional groups, it may have potential applications in the development of new drugs or chemical compounds.

Molecular complexity

As a building block, it can be used to create more complex molecules with diverse properties and applications.

Research and development

Further research may be needed to fully understand the properties and potential applications of 1,5,9-Triazacyclotridecan-4-one, 3-hydroxy-9-[(2E)-1-oxo-3-phenyl-2-propenyl]-2-phenyl-, (2R,3S)-.

Safety and handling

As with any chemical compound, proper safety precautions and handling procedures should be followed when working with this substance.

Upstream product

• 102-92-1 Cinnamoyl chloride 
• 623571-27-7 (-)-(2R,3S)-3-hydroxy-2-phenyl-1,5,9-triazatridecan-4-one 
• 623571-45-9 (+)-(2R,3R)-3-hydroxy-9-[(4-methylphenyl)sulfonyl]-2-phenyl-1,5,9-triazacyclotridecan-4-one 
• 623571-26-6 (-)-(2R,3S)-3-hydroxy-9-[(4-methylphenyl)sulfonyl]-2-phenyl-1,5,9-triazatridecan-4-one 
• 623571-23-3 (-)-(12R,15R)-6-[(4-methylphenyl)sulfonyl]-15-phenyl-13-oxa-14-thia-1,6,10-triazabicyclo[10.2.1]pentadecan-11-one 14-oxide 
• 623571-24-4 (-)-(12R,15R)-6-[(4-methylphenyl)sulfonyl]-15-phenyl-13-oxa-14-thia-1,6,10-triazabicyclo[10.2.1]pentadecan-11-one 14,14-dioxide 
• 623571-39-1 (+)-(2R,3S)-N-{3-{[(4-methylphenyl)sulfonyl]{4-[(trifluoroacetyl)amino]butyl}amino}propyl}-3-phenyloxiranecarboxamide 
• 623571-36-8 potassium (-)-(2R,3S)-trans-N-(3-bromopropyl)-3-phenyloxiranecarboxamide 

Relevant academic research and scientific papers

Synthesis of the macrocyclic spermidine alkaloid (±)-(2R*,3R*)-3-hydroxycelacinnine

The macrocyclic lactam alkaloid (±)-(2R*,3R*)-3-hydroxycelacinnine (1) derived from spermidine was synthesized via stereoselective epoxide-ring opening with magnesium azide and cesium carbonate promoted macrocyclization of the ditosylated diamino precursor 12 with 1,4-dibromobutane in the two key steps (Scheme 2). 1H- and 13C-NMR Signal assignments from COSY, HSQC, and HMBC 2D NMR data of the synthesized 1 were compared with the earlier-described data of the natural 3-hydroxycelacinnine. The similarity of their 13C-NMR spectra point to the correctness of the proposed constitutional formula for natural 3-hydroxycelacinnine; however, different 1H-NMR chemical shifts and coupling constants (J(2,3) = 9.0 vs. 1.2 Hz, resp.) in the α-hydroxy-β-amino lactam moiety suggest that natural 3-hydroxycelacinnine is the 2,3-cis-epimer of one synthetic (±)-1.

Synthesis of the spermidine alkaloids (-)-(2R,3R)- and (-)-(2R,3S)-3-hydroxycelacinnine: Macrocyclization with oxirane-ring opening and inversion via cyclic sulfamidates

The two epimers (-)-1a and (-)-1b of the macrocyclic lactama kaloid 3-hydroxycelacinnine with the (2R,3R) and (2R,3S) absolute configurations, respectively, were synthesized by an alternative route involving macrocyclization with the regio- and stereoselective oxirane-ring opening by the terminal amino group (Schemes 2 and 6). Properly N-protected chiral trans-oxirane precursors provided (2R,3R)-macrocycles after a one-pot deprotection-macrocyclization step under moderate dilution (0.005-0.01M). The best yields (65-85%) were achieved with trifluoroacetyl protection. Macrocyclization of the corresponding cis-oxiranes was unsuccessful for steric reasons. Inversion at OH-C(3) via nucleophilic displacement of the cyclic sulfamidate derivative with NaNO2 led to (2R,3S)-macrocycles. The synthesized (-)-(2R,3S)-3-hydroxycelacinnine ((-)-1b) was identical to the natural alkaloid.