816429-58-0

Basic information

• Product Name: (S,S)-3-BENZYL-1,4-DIAZABICYCLO[4.3.0]NONANE
• Synonyms: (S,S)-3-BENZYL-1,4-DIAZABICYCLO[4.3.0]NONANE;3-Benzyl-octahydro-pyrrolo[1,2-a]pyrazine;(3S,9S)-3-Benzyl-1,4-diazabicyclo[4.3.0]nonane;(3S,9S)-3-Benzyloctahydropyrrolo[1,2-a]pyrazine;(S, S)-3-Benzyl-octahydro-pyrrolo[1,2-a]pyrazine;(3S,6S)-3-Benzyl-1,4-diazabicyclo[4.3.0]nonane
• CAS NO: 816429-58-0
• Molecular Formula: C14H20N2
• Molecular Weight: 216.32
• Mol File: 816429-58-0.mol

Chemical Properties

• Boiling Point: 101-103℃/1mm
• Flash Point: 139.7°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 0.000131mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: (S,S)-3-BENZYL-1,4-DIAZABICYCLO[4.3.0]NONANE(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-3-BENZYL-1,4-DIAZABICYCLO[4.3.0]NONANE(816429-58-0)
• EPA Substance Registry System: (S,S)-3-BENZYL-1,4-DIAZABICYCLO[4.3.0]NONANE(816429-58-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25
• Safety Statements: 45
• Hazardous Substances Data: 816429-58-0(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Catalysis:
(S,S)-3-Benzyl-1,4-diazabicyclo[4.3.0]nonane is used as a chiral ligand in asymmetric catalysis, where it plays a crucial role in enhancing the selectivity and efficiency of chemical reactions, leading to the production of enantiomerically pure compounds.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (S,S)-3-Benzyl-1,4-diazabicyclo[4.3.0]nonane is utilized in the synthesis of various drugs and therapeutic agents. Its unique structure contributes to the development of new and effective medications.
Used in Material Science:
(S,S)-3-Benzyl-1,4-diazabicyclo[4.3.0]nonane has shown promise in the development of new materials due to its structural properties, making it a valuable compound in material science research and applications.
Used in Medicinal Chemistry:
Due to its demonstrated biological activity, (S,S)-3-Benzyl-1,4-diazabicyclo[4.3.0]nonane is of interest in medicinal chemistry for the development of new drugs and therapeutic agents, potentially leading to advancements in healthcare and treatment options.

InChI:InChI=1/C14H20N2/c1-2-5-12(6-3-1)9-13-11-16-8-4-7-14(16)10-15-13/h1-3,5-6,13-15H,4,7-11H2/t13-,14-/m0/s1

Upstream product

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 83825-04-1 L-phenylalanine-L-proline methyl ester 
• 126251-10-3 H-D-Phe-L-Pro-OMe 
• 126251-09-0 Boc-D-Phe-L-Pro-OMe 
• 18942-49-9 Boc-D-Phe-OH 
• 26488-24-4 (3R,8aS)-hexahydro-3-(phenylmethyl)pyrrolo[1,2-a]pyrazine-1,4-dione 
• 38017-89-9 t-butyloxycarbonyl-L-phenylalanyl-L-proline methyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 5654-85-3 (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione 

Relevant articles and documents

Enantioselective Henry reaction catalyzed by C2-symmetric chiral diamine-copper(II) complex

A copper(II) complex of C2-symmetric diamine has been proved to be an efficient catalyst for the enantioselective Henry reaction between nitroalkanes and various aldehydes to provide β-hydroxy nitroalkanes in high yields (up to 97%), moderate diastereoselectivities (up to 71:29) and excellent enantiomeric excesses (up to 96%). The chiral nitroaldol adduct obtained has been further converted into chiral aziridine in few steps.

Design, synthesis, and biological evaluation of a new class of small molecule peptide mimetics targeting the melanocortin receptors

A new bicyclic template has been developed for the synthesis of peptide mimetics. Straightforward synthetic steps, starting from amino acids, allow the facile construction of a wide range of analogs. This system was designed to target the melanocortin receptors (MCRs), with functional group selection based on a known pharmacophore and guidance from molecular modeling to rationally identify positional and stereochemical isomers likely to be active. The functions of hMCRs are critical to myriad biological activities, including pigmentation, steroidogenesis, energy homeostasis, erectile activity, and inflammation. These G-protein-coupled receptors (GPCRs) are targets for drug discovery in a number of areas, including cancer, pain, and obesity therapeutics. All compounds from this series tested to date are antagonists which bind with high affinity. Importantly, many are highly selective for a particular MCR subtype, including some of the first completely hMC5R-selective antagonists reported.