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Ligands
Nitrogen-Donor Ligands
Oxazole Ligands, Oxazoline Ligands, Thiazole Ligands
(-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

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

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Catalog Number

ACM175166491-2

Product Name

Structure

CAS

175166-49-1

Product Overview
Usage

Synonyms

Bis((3aS,8aR)-8,8a-dihydro-3aH-indeno[1,2-d]oxazol-2-yl)methane

IUPAC Name

(3aR,8bS)-2-[[(3aR,8bS)-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

330.38

Molecular Formula

C21H18N2O2

Canonical SMILES

C1C2C(C3=CC=CC=C31)N=C(O2)CC4=NC5C(O4)CC6=CC=CC=C56

InChI

BDHSVQLSNIGJNC-JYWFKMLOSA-N

InChI Key

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+/m1/s1

Boiling Point

493.2±45.0 °C(Predicted)

Melting Point

224 °C

Purity

>98.0%(LC)(N)

Appearance

White powder

Complexity

563

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

330.136827821

H-Bond Acceptor

Heavy Atom Count

Isomeric SMILES

C1[C@@H]2[C@H](C3=CC=CC=C31)N=C(O2)CC4=N[C@@H]5[C@H](O4)CC6=CC=CC=C56

Monoisotopic Mass

330.136827821

Rotatable Bond Count

Topological Polar Surface Area

43.2 Å²

Application

(-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] serves as a versatile chiral ligand, facilitating various synthetic processes in organic chemistry. This compound is particularly useful in the preparation of oxazole α-hydroxy esters through the intermolecular Alder-Ene reaction, an option that broadens the scope for creating complex molecular structures. Additionally, it plays a critical role in the atom transfer radical polymerization of methyl methacrylate, contributing to the development of precision polymers with specific properties. Furthermore, this chiral ligand is employed in the copper-catalyzed synthesis of isoxazolidine derivatives, where it assists in the reaction between nitrone and α,β-unsaturated acyl phosphonate. Through these applications, (-)-2,2'-Methylenebis[(3aS,8aR)-3a,8a-dihydro-8H-indeno[1,2-d]oxazole] enhances the efficiency and selectivity of chemical reactions, thus advancing the field of synthetic organic chemistry.

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CAS
Size
Purity
Price
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175166-49-1
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>98.0%(LC)(N)
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