138517-66-5 Usage
Description
(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine is a chiral diamine compound known for its unique structural properties and reactivity. It is characterized by its specific stereochemistry, where the two amine groups are located at the 11 and 12 positions in a stereospecific (S,S) configuration. (11S,12S)-9,10-DIHYDRO-9,10-ETHANOANTHRACENE-11,12-DIAMINE is highly valuable in the field of organic chemistry due to its ability to participate in various chemical reactions and form a range of useful products.
Uses
Used in Chemical Synthesis:
(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine is used as a reactant for the synthesis of pyridine-based C2-symmetrical chiral organocatalysts via palladium-catalyzed coupling reactions with 2-bromo-4-(alkylamino)pyridine. This application is significant as it contributes to the development of novel chiral catalysts that can be employed in asymmetric catalysis, leading to the production of enantiomerically pure compounds with potential applications in pharmaceuticals and agrochemicals.
Used in Material Science:
In the field of material science, (11S,12S)-9,10-dihydro-9,10-ethanoanthracene-11,12-diamine is used as a reactant to prepare porous organic imine cages through cycloimination reactions with triformylbenzene. These porous organic cages have potential applications in gas storage, separation processes, and as platforms for catalysis due to their unique structural properties and high surface area.
Used in Catalysis:
(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine is also utilized in the synthesis of Ga/Yb-Schiff base complexes, which serve as catalysts for the asymmetric synthesis of 5-amino-2-(hydroxyalkyl)oxazoles. This process involves the enantioselective α-addition of α-isocyano amides to aldehydes, and the resulting oxazoles are important structural motifs found in various biologically active compounds and pharmaceuticals. The use of this chiral diamine in the development of such catalysts highlights its importance in the field of homogeneous catalysis and enantioselective synthesis.
Check Digit Verification of cas no
The CAS Registry Mumber 138517-66-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,8,5,1 and 7 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 138517-66:
(8*1)+(7*3)+(6*8)+(5*5)+(4*1)+(3*7)+(2*6)+(1*6)=145
145 % 10 = 5
So 138517-66-5 is a valid CAS Registry Number.
InChI:InChI=1/C16H16N2/c17-15-13-9-5-1-2-6-10(9)14(16(15)18)12-8-4-3-7-11(12)13/h1-8,13-16H,17-18H2/t13?,14?,15-,16-/m0/s1
138517-66-5Relevant articles and documents
Total Synthesis of (-)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane
Coffinier, Romain,Assal, Mourad El,Peixoto, Philippe A.,Bosset, Cyril,Miqueu, Karinne,Sotiropoulos, Jean-Marc,Pouységu, Laurent,Quideau, Stéphane
, p. 1120 - 1123 (2016)
The first total and biomimetic synthesis of the natural bis(sesquiterpene) (-)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphe
A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations
Trost, Barry M.,Van Vranken, David L.,Bingel, Carsten
, p. 9327 - 9343 (2007/10/02)
A new class of ligands for asymmetric transition metal catalysis based on 2-(diphenylphosphino)benzoic acid was used in a mechanistically-defined palladium-catalyzed reaction in which enantiodifferentiation was the result of selective ionization of substr
