227940-72-9

Basic information

• Product Name: tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate
• Synonyms: tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate;3,7-Diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester;7-tert-Butoxycarbonyl-3,7-diazabicyclo[3.3.1]nonane;tert-butyl 8-{3,7-diazabicyclo[3.3.1]nonan-1-yl}-2-ethyloctanoate;3-Boc-3,7-diazabicyclo[3.3.1]nonane
• CAS NO: 227940-72-9
• Molecular Formula: C₁₂H₂₂N₂O₂
• Molecular Weight: 226.31528
• Mol File: 227940-72-9.mol

Chemical Properties

• Boiling Point: 313.8±35.0 °C(Predicted)
• Appearance: /
• Density: 1.052
• PKA: 10.57±0.20(Predicted)
• CAS DataBase Reference: tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate(227940-72-9)
• EPA Substance Registry System: tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate(227940-72-9)

Safety Data

• Hazardous Substances Data: 227940-72-9(Hazardous Substances Data)

Usage

Uses

Used in Organometallic Chemistry:
Tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate is utilized as a ligand for its capacity to form stable complexes with metal ions, which is crucial in organometallic chemistry for enhancing the stability and reactivity of metal complexes.
Used in Catalysis:
In the field of catalysis, tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate serves as a ligand to improve the efficiency and selectivity of catalytic reactions, taking advantage of its unique structural features.
Used in Asymmetric Synthesis:
As a chiral ligand, tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate is employed in asymmetric synthesis to induce enantioselectivity, enabling the production of optically active compounds with a single enantiomer predominating, which is vital for the synthesis of pharmaceuticals and agrochemicals.
Used in Chemical Research:
Tert-butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate is also applied in chemical research for studying the properties and reactions of metal complexes and for developing new synthetic methodologies.
Used in Industrial Applications:
Its industrial applications stem from its versatility in forming stable complexes and its utility in asymmetric synthesis, making it valuable in the production of specialty chemicals, pharmaceutical intermediates, and other high-value products.

Upstream product

• 227940-70-7 7-benzyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester 
• 227940-71-8 tert-Butyl 7-benzyl-3,7-diazabicyclo[3.3. 1]-nonane-3-carboxylate 

Downstream Products

• 1429776-76-0 tert-butyl 7-(5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl)-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate 
• 1429773-09-0 (7-(5-chlorobenzo[d]oxazol-2-yl)-3,7-diazabicyclo[3.3.1]nonan-3-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone 

Relevant articles and documents

Unsymmetrical pincer CNN palladium complex of 7-ferrocenylmethyl-3-methyl-3,7-diazabicyclo[3.3.1]nonane

The new unsymmetrical ferrocenyl containing bispidine derivative 7 was synthesized as a ligand precursor in five steps starting from N-Boc-4-oxopiperidine. The corresponding palladium CNN pincer complex 8 was prepared by direct cyclopalladation of the ligand 7 with Li2PdCl4 in MeOH. The molecular structure of the obtained palladacycle was determined by multinuclear NMR (1H, 13C, 15N) and confirmed by X-ray diffraction analysis. The pincer complex 8 demonstrated high catalytic activity in some cross-coupling reactions of aryl halides with phenylboronic acid, norbornene and ethyl acrylate.

Modulation of prion polymerization and toxicity by rationally designed peptidomimetics

Misfolding and aggregation of cellular prion protein is associated with a large array of neurological disorders commonly called the transmissible spongiform encephalopathies. Designing inhibitors against prions has remained a daunting task owing to limited information about mechanism(s) of their pathogenic self-assembly. Here, we explore the antiprion properties of a combinatorial library of bispidine-based peptidomimetics (BPMs) that conjugate amino acids with hydrophobic and aromatic side chains. Keeping the bispidine unit unaltered, a series of structurally diverse BPMs were synthesized and tested for their prion-modulating properties. Administration of Leu- and Trp-BPMs delayed and completely inhibited the amyloidogenic conversion of human prion protein (HuPrP), respectively. We found that each BPM induced the HuPrP to form unique oligomeric nanostructures differing in their biophysical properties, cellular toxicities and response to conformation-specific antibodies. While Leu-BPMs were found to stabilize the oligomers, Trp-BPMs effected transient oligomerization, resulting in the formation of non-toxic, nonfibrillar aggregates. Yet another aromatic residue, Phe, however, accelerated the aggregation process in HuPrP. Molecular insights obtained through MD (molecular dynamics) simulations suggested that each BPM differently engages a conserved Tyr 169 residue at the α2-β2 loop of HuPrP and affects the stability of α2 and α3 helices. Our results demonstrate that this new class of molecules having chemical scaffolds conjugating hydrophobic/aromatic residues could effectively modulate prion aggregation and toxicity.

A tryptophan-containing fluorescent intramolecular complex as a designer peptidic proton sensor

Pyrene and tryptophan groups judiciously placed on a novel molecular scaffold, namely, bispidine exhibited fluorescence due to the formation of an unprecedented emissive intramolecular complex in polar solvents. Upon protonation, the emission signal from the pyrene unit enhances at the expense of the emission signal from the complex. The probe demonstrates good sensitivity, excellent selectivity, and adequate reversibility towards proton sensing. The present design based on the bispidine scaffold opens up newer opportunities for the design of novel bispidine-peptide sensors.

Synthesis and evaluation of dual antiplatelet activity of bispidine derivatives of N-substituted pyroglutamic acids

N-aralkylpyroglutamides of substituted bispidine were prepared and evaluated for their ability to inhibit collagen induced platelet aggregation, both in vivo and in vitro. Some compounds showed high anti-platelet efficacy (in vitro) of which six inhibited

3,7-DIAZABICYCLO[3.3.1 ]NONANE CARBOXAMIDES AS ANTITHROMBOTIC AGENTS

The present invention relates to the 3,7-diazabicyclo[3.3.1]nonane carboxamides and process for preparation thereof. The present invention further relates to the compounds of general formula (1) possessing anti-thrombotic (anti-platelet) activities. The invention also relates to use of these moieties as inhibitors of collagen induced platelet adhesion and aggregation mediated through collagen receptors both in vitro and in vivo. Further, invention also relates these class of compounds exhibiting anti-platelet efficacy through dual mechanism inhibited both collagen as well as U46619 (thromboxane receptor agonist) induced platelet aggregation. General formula (1) Wherein, R' is; wherein R is selected from alkyl, acyl, tosyl, tert-butyloxycarbonyl, araalkyl or substituted araalkyl groups; R'' is selected preferably from halogen, cyano, lower alkyl, aryl, substituted aryl, and tosyl groups; R1 is selected from hydrogen and lower alkyl groups; R2 is selected from lower alkyl and aryl groups; R3 is selected from tert-butyloxycarbonyl and bezyloxycarbonyl groups; n = 0,1.

3,7-DIAZABICYCLO[3.3.1]NONANE AND 9-OXA-3,7-DIAZABICYCLO[3.3.1]NONANE DERIVATIVES

The present invention relates to 3,7-diazabicyclo[3.3.1]nonane and 9-oxa-3,7- diazabicyclo[3.3.1 ]nonane derivatives of formula (I) wherein Ar1 and Ar2 are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as orexin receptor antagonists.

Bispidine as a helix inducing scaffold: Examples of helically folded linear peptides

We designed and synthesized bispidine-anchored peptides and showed that these peptides as small as B3 (containing four chiral α-amino acid residues) adopt a right handed helical conformation. Bispidine anchored linear peptide B3 adopts a helical conformat

Bispidine as a secondary structure nucleator in peptides

Here we describe bispidine as a scaffold for inducing open turn-like and beta sheet conformations on the attached peptides depending on the mode of attachment of peptides to the scaffold. Various bispidine-peptide conjugates were designed and synthesized to demonstrate the versatility of the scaffold.

NICOTINIC ACETYLCHOLINE RECEPTOR SUB-TYPE SELECTIVE AMIDES OF DIAZABICYCLOAL KANES

The present invention relates to compounds of the following formula (I) that bind to and modulate the activity of neuronal nicotinic acetylcholine receptors, to processes for preparing these compounds, to pharmaceutical compositions containing these compounds, and to methods of using these compounds for treating a wide variety of conditions and disorders, including those associated with dysfunction of the central nervous system (CNS).

NICOTINIC ACETYLCHOLINE RECEPTORSUB-TYPE SELECTIVE AMIDES OF DIAZABICYCLOALKANES

Compounds, pharmaceutical compositions including the compounds, and methods of preparation and use thereof are disclosed. The compounds are amide compounds which can be prepared from certain heteoraryl carboxylic acids and certain diazabicycloalkanes. The