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(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

Catalog Number
ACM180186941-1
Product Name
(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]
Structure
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CAS
180186-94-1
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Synonyms
MFCD06797115; SCHEMBL12269622; [3aR-[2(3'aR,8'aS),3'abeta,8'abeta]]-(+)-2,2'-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-]oxazole]; (+)-2,2-methylenebis[(3ar,8as)-3a,8a-dihydro-8h-indeno[1,2-d]oxazole]; (+)-2,2-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole], 98%; (+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]; ANW-23004; DTXSID50361456; I14-56853; 2,2'-Methylenebis(3abeta,8abeta-dihydro-8H-indeno[1,2-d]oxazole);
IUPAC Name
(3aS,8bR)-2-[[(3aS,8bR)-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-yl]methyl]-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazole;
Molecular Weight
330.387g/mol
Molecular Formula
C21H18N2O2;
Canonical SMILES
C1C2C(C3=CC=CC=C31)N=C(O2)CC4=NC5C(O4)CC6=CC=CC=C56;
InChI
InChI=1S/C21H18N2O2/c1-3-7-14-12(5-1)9-16-20(14)22-18(24-16)11-19-23-21-15-8-4-2-6-13(15)10-17(21)25-19/h1-8,16-17,20-21H,9-11H2/t16-,17-,20+,21+/m0/s1;
InChI Key
BDHSVQLSNIGJNC-ZCLUNYJNSA-N;
Complexity
563
Covalently-Bonded Unit Count
1
Defined Atom Stereocenter Count
4
Exact Mass
330.137g/mol
H-Bond Acceptor
4
Heavy Atom Count
25
Monoisotopic Mass
330.137g/mol
Rotatable Bond Count
2
Topological Polar Surface Area
43.2A^2
Application
(+)-2,2'-Methylenebis[(3aR,8aS)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] serves as a C2 symmetric chiral ligand leveraging a bis(oxazoline) framework, specifically designed for enantioselective catalysis. This compound, presenting as a white powder, is adept at forming bidentate coordination complexes thanks to the oxazoline nitrogen's strong affinity for various metals. These properties make it particularly valuable as the copper complex version of this chiral ligand acts as a reusable catalyst, effectively facilitating cyclopropanation reactions between styrene and ethyl diazoacetate.
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