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- (11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine
(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine
PRICE INQUIRYCatalog Number
ACM138517665
Product Name
(11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/138517-66-5.gif)
CAS
138517-66-5
Synonyms
(S,S)-11,12-Diamino-9,10-dihydro-9,10-ethanoanthracene
IUPAC Name
(15S,16S)-tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15,16-diamine
Molecular Weight
236.31
Molecular Formula
C16H16N2
Canonical SMILES
C1=CC=C2C3C(C(C(C2=C1)C4=CC=CC=C34)N)N
InChI
NWDYSRZJOLDMRE-CKUJCDMFSA-N
InChI Key
InChI=1S/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
Boiling Point
396.72ºC at 760 mmHg
Melting Point
152.5-153.9 °C
Flash Point
231.6ºC
Purity
98%
Density
1.195g/cm³
Appearance
Off-white powder
Complexity
273
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
2
Exact Mass
236.13100
H-Bond Acceptor
2
H-Bond Donor
2
Heavy Atom Count
18
Isomeric SMILES
C1=CC=C2C3[C@@H]([C@H](C(C2=C1)C4=CC=CC=C34)N)N
Monoisotopic Mass
236.131g/mol
Topological Polar Surface Area
52A^2
Application
The purpose of (11S,12S)-9,10-Dihydro-9,10-ethanoanthracene-11,12-diamine, a chiral diamine, is to serve as a versatile reactant in various chemical syntheses. It is utilized in the synthesis of pyridine-based C2-symmetrical chiral organocatalysts through a palladium-catalyzed coupling with 2-bromo-4-(alkylamino)pyridine. Additionally, it plays a crucial role in preparing porous organic imine cages via cycloimination with triformylbenzene. Furthermore, this compound is instrumental in forming a Ga/Yb-Schiff base complex, acting as a catalyst for the asymmetric synthesis of 5-amino-2-(hydroxyalkyl)oxazoles, which involves the enantioselective α-addition of α-isocyano amides to aldehydes.
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