3,7-Diazabicyclo[3.3.1]nonane

Base Information

• Chemical Name: 3,7-Diazabicyclo[3.3.1]nonane
• CAS No.: 280-74-0
• Molecular Formula: C7H14N2
• Molecular Weight: 126.202
• Hs Code.: 2933990090
• UNII: CH6VDH22TL
• DSSTox Substance ID: DTXSID90182283
• Nikkaji Number: J1.502.563H,J11.397B
• Wikipedia: Bispidine
• Wikidata: Q866620
• ChEMBL ID: CHEMBL3094064
• Mol file: 280-74-0.mol

Synonyms:3,7-diazabicyclo(3.3.1)nonane

Chemical Property of 3,7-Diazabicyclo[3.3.1]nonane

Chemical Property:

• Vapor Pressure: 0.14mmHg at 25°C
• Melting Point: 234-236 °C
• Refractive Index: 1.469
• Boiling Point: 216.4 °C at 760 mmHg
• PKA: 11.05±0.20(Predicted)
• Flash Point: 107.1 °C
• PSA: 24.06000
• Density: 0.95 g/cm³
• LogP: 0.47290
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 126.115698455
• Heavy Atom Count: 9
• Complexity: 83.1

Purity/Quality:

99% ^*data from raw suppliers

3,7-DIAZABICYCLO[3.3.1]NONANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CNCC1CNC2
• General Description: 3,7-Diazabicyclo[3.3.1]nonane (bispidine) is a structurally rigid bicyclic diamine with potential utility in asymmetric synthesis, particularly as a chiral ligand or scaffold for Lewis acids. The asymmetric synthesis of a C₂-symmetric 2-endo,6-endo-disubstituted derivative demonstrates its versatility, enabling the introduction of stereochemical control for applications in catalysis or molecular recognition. The scaffold's rigid framework and ability to accommodate diverse substituents make it a promising candidate for designing enantioselective systems.

Technology Process of 3,7-Diazabicyclo[3.3.1]nonane

There total 15 articles about 3,7-Diazabicyclo[3.3.1]nonane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3,7-Bis(carbethoxy)-3,7-diazabicyclo[3.3.1]nonane (341484-51-3) → 3,7-diazabicyclo{3.3.1}nonane (280-74-0)

Guidance literature:

3,7-Bis(carbethoxy)-3,7-diazabicyclo[3.3.1]nonane; With potassium hydroxide; In ethanol; for 12h; Heating;

for 20h; Heating;

DOI:10.1055/s-2001-11427

Reference yield: 98.0%

tert-Butyl 3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (227940-72-9) → 3,7-diazabicyclo{3.3.1}nonane (280-74-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2011.11.112

Reference yield: 86.0%

N,N'-dibenzyl-3,7-diazabicyclo[3.3.1]nonane (59009-71-1) → 3,7-diazabicyclo{3.3.1}nonane (280-74-0)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In methanol; for 18h;

DOI:10.1002/(SICI)1099-0690(200002)2000:3<391::AID-EJOC391>3.0.CO;2-R

upstream raw materials:

pyridine-3,5-dicarbonitrile

N,N'-dibenzyl-3,7-diazabicyclo[3.3.1]nonane

3,7-Bis(carbethoxy)-3,7-diazabicyclo[3.3.1]nonane

3,7-diallyl-3,7-diazabicyclo[3.3.1]-nonane

Downstream raw materials:

3,7-diaza-bicyclo[3.3.1]nonane-3,7-dicarboxylic acid diphenyl ester

1,3-diaza-adamantane

3,7-dibenzoyl-3,7-diaza-bicyclo[3.3.1]nonane

3,7-bis-(toluene-4-sulfonyl)-3,7-diaza-bicyclo[3.3.1]nonane

Refernces

First asymmetric synthesis of a C₂-symmetric 2-endo,6-endo-disubstituted bispidine

10.1016/j.tetasy.2007.06.010

The study details the enantioselective synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine (3,7-diazabicyclo[3.3.1]nonane). The key chemical involved is the protected b-amino ester methyl (R)-3-{N-benzyl-N[(S)-1-phenylethyl]amino}-3-phenylpropionate, which undergoes a Michael addition to its a-methylene derivative to form an anti,anti-configured a,a-methylene-bridged bis(b-amino ester) as the major diastereomer. This intermediate is then transformed into the final product, (1R,2R,5R,6R)-2,6-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane, through deprotection, reduction, and cyclization steps. The synthesis is significant as it provides a new route to C2-symmetric bispidines, which have potential applications in asymmetric synthesis as chiral ligands or backbones for Lewis acids. The study also explores various synthetic routes and conditions to optimize the yield and diastereoselectivity of the key Michael addition step, ultimately achieving the target compound in six steps with a 15% overall yield.

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