59009-71-1

Basic information

• Product Name: 3,7-Diazabicyclo[3.3.1]nonane, 3,7-bis(phenylmethyl)-
• Synonyms: N,N'-dibenzyl-3,7-diazabicyclo[3.3.1]nonane;3,7-Diazabicyclo[3.3.1]nonane,3,7-bis(phenylmethyl);benzyl bispidine;3,7-dibenzyl-3,7-diaza-bicyclo[3.3.1]nonane;3,7-dibenzyl-7-aza-3-azoniabicyclo[3.3.1]nonane;N-N'-Dibenzyl-bispidin
• CAS NO: 59009-71-1
• Molecular Formula: C21H26N2
• Molecular Weight: 306.451
• Mol File: 59009-71-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3,7-Diazabicyclo[3.3.1]nonane, 3,7-bis(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-Diazabicyclo[3.3.1]nonane, 3,7-bis(phenylmethyl)-(59009-71-1)
• EPA Substance Registry System: 3,7-Diazabicyclo[3.3.1]nonane, 3,7-bis(phenylmethyl)-(59009-71-1)

Safety Data

• Hazardous Substances Data: 59009-71-1(Hazardous Substances Data)

Upstream product

• 28781-92-2 Propane-1,1,3,3-tetracarboxylic acid tetramethyl ester 
• 100-46-9 benzylamine 
• 42259-65-4 1,5-dibromo-2,4-bis-bromomethyl-pentane 
• 909037-16-7 3,7-dibenzyl-9,9-(1,3-dithiolan-2-yl)-3,7-diazabicyclo[3.3.1]nonane 
• 100-51-6 benzyl alcohol 
• 59009-70-0 3,7-bis(phenylmethyl)-3,7-diazabicyclo[3.3.1]nonan-9-one 

Downstream Products

• 69407-32-5 3-benzyl-3,7-diaza-bicyclo[3,3,1]nonane 
• 280-74-0 3,7-diazabicyclo{3.3.1}nonane 

Relevant articles and documents

Benzyl bispidine as an efficient replacement for (-)-sparteine in ring opening polymerisation

The synthesis and application of a dibenzyl-functionalized bispidine, in combination with 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) co-catalyst, has been demonstrated to be an excellent catalyst for the controlled ring-opening polymerisation (ROP) of lactide and cyclic carbonate monomers. Notably, the polymerisation proceeds with negligible transesterification or epimerisation, with the polymerisation of stereopure l-lactide affording highly crystalline poly(lactide) with a Tm of 156 °C. ROP of racemic lactide results in the observation of a modest degree of stereocontrol such that the probability of isotactic enchainment, Pm = 0.74. Comparison of a range of alternative hydrogen bond donor co-catalysts revealed that TU displayed the highest polymerisation rates in combination with the dibenzyl-functionalized bispidine.

BISPIDINE COMPOUNDS USEFUL IN THE TREATMENT OF CARDIAC ARRHYTHMIAS

There is provided compounds of formula I, wherein R1, R2, R3, R4, R5a, R5b, R6, X, A, B and D have meanings given in the description, which are useful in the prophylaxis and in the treatment of arrhythmias, in particular atrial and ventricular arrhythmias.

Synthesis of chiral amino alcohols embodying the bispidine framework and their application as ligands in enantioselectively catalyzed additions to C=O and C=C groups

Two generally applicable routes for the synthesis of chiral amino alcohols embodying the bispidine framework have been developed. In linear route A the bispidine framework is built up successively from chiral primary amines via intermediate formation of a piperidinone and a bispidinone. In convergent route B an achiral bispidine is formed first and then the N- substituents are introduced by reaction of the nitrogen bases with chiral electrophiles. In order to determine if the bispidine core and its N- substituents can influence the steric course of enantioselective transformations, bispidine amino alcohols built up by these two routes were investigated as chiral ligands in the enantioselectively catalyzed addition of diethylzinc to aldehydes and chalcone. In general, tridentate ligands containing one chiral amino alcohol fragment and a second amino substituent without a stereogenic center were more efficient than tetradentate ligands with two amino alcohol structural units. With the best ligands the enantioselective addition of diethylzinc to aromatic and aliphatic aldehydes proceeded with 83-98% ee and the nickel-catalyzed addition of diethylzinc to chalcone was achieved with up to 85% ee.