851526-81-3

Basic information

• Product Name: tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate
• Synonyms: tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate
• CAS NO: 851526-81-3
• Molecular Formula: C11H20N2O2
• Molecular Weight: 212.2887
• EINECS: -0
• Mol File: 851526-81-3.mol

Chemical Properties

• Boiling Point: 295.4±13.0 °C(Predicted)
• Appearance: /
• Density: 1.076±0.06 g/cm3(Predicted)
• PKA: 10.54±0.20(Predicted)
• CAS DataBase Reference: tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate(851526-81-3)
• EPA Substance Registry System: tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate(851526-81-3)

Safety Data

• Hazardous Substances Data: 851526-81-3(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Catalysis:
Tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate is utilized as a chiral ligand in asymmetric catalysis, where it plays a crucial role in enhancing the enantioselectivity of reactions. Its steric properties and electronic effects contribute to the successful formation of enantiomerically pure products, which are essential in the synthesis of pharmaceuticals and agrochemicals.
Used in Metal-Catalyzed Transformations:
In metal-catalyzed reactions, tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate serves as a versatile ligand, modulating the reactivity and selectivity of metal catalysts. Its use in these transformations allows for the development of efficient and selective synthetic routes to complex organic molecules, including those with potential applications in the pharmaceutical and materials science industries.
Used in Drug Discovery and Development:
Tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate has been investigated for its role in the synthesis of pharmaceutical intermediates. Its unique structural features and reactivity make it a valuable building block in the development of novel drug candidates. Its potential applications in medicinal chemistry include the synthesis of bioactive compounds, optimization of drug candidates, and the discovery of new therapeutic agents.
Used in Organic Synthesis:
As a derivative of DABCO, tert-butyl 3,6-diazabicyclo[3.2.1]octane-3-carboxylate is employed as a catalyst and base in various organic synthesis reactions. Its ability to control regioselectivity and enantioselectivity makes it a valuable tool for the preparation of complex organic molecules with high levels of stereochemical control, which is crucial for the development of enantiomerically pure compounds in the pharmaceutical and chemical industries.

Upstream product

• 851526-82-4 1-(3-Benzyl-3,6-diazabicyclo[3.2.1]oct-6-yl)-2,2,2-trifluoro-ethanone 
• 848591-68-4 tert-butyl 3-benzyl-3,6-diazabicyclo[3.2.1]octane-6-carboxylate 

Relevant articles and documents

Structure-activity studies and analgesic efficacy of N-(3-pyridinyl)- bridged bicyclic diamines, exceptionally potent agonists at nicotinic acetylcholine receptors

A series of exceptionally potent agonists at neuronal nicotinic acetylcholine receptors (nAChRs) has been investigated. Several N-(3-pyridinyl) derivatives of bridged bicyclic diamines exhibit double-digit-picomolar binding affinities for the α4β2 subtype, placing them with epibatidine among the most potent nAChR ligands described to date. Structure-activity studies have revealed that substitutions, particularly hydrophilic groups in the pyridine 5-position, differentially modulate the agonist activity at ganglionic vs central nAChR subtypes, so that improved subtype selectivity can be demonstrated in vitro. Analgesic efficacy has been achieved across a broad range of pain states, including rodent models of acute thermal nociception, persistent pain, and neuropathic allodynia. Unfortunately, the hydrophilic pyridine substituents that were shown to enhance agonist selectivity for central nAChRs in vitro tend to limit CNS penetration in vivo, so that analgesic efficacy with an improved therapeutic window was not realized with those compounds.

Substituted diazabicycloalkane derivatives

Compounds of formula (I) [in-line-formulae]Z-Ar1—Ar2??(I) [/in-line-formulae] wherein Z is a diazabicyclic amine, Ar1 is a 5- or 6-membered aromatic ring, and Ar2 is selected from the group consisting of an unsubstituted or substituted 5- or 6-membered heteroaryl ring; unsubstituted or substituted bicyclic heteroaryl ring; 3,4-(methylenedioxy)phenyl; carbazolyl; tetrahydrocarbazolyl; naphthyl; and phenyl; wherein the phenyl is substituted with 0, 1, 2, or 3 substituents in the meta- or para-positions. The compounds are useful in treating conditions or disorders prevented by or ameliorated by α7 nAChR ligands. Also disclosed are pharmaceutical compositions comprising compounds of formula (I) and methods for using such compounds and compositions.