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467073

Sigma-Aldrich

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

98%

Synonym(s):

[3aS-[2(3′aR*,8′aS*),3′aα,8′aα]]-(−)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole]

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About This Item

Empirical Formula (Hill Notation):
C21H18N2O2
CAS Number:
175166-49-1
Molecular Weight:
330.38
MDL number:
MFCD00799561
UNSPSC Code:
12352005
PubChem Substance ID:
24870382
NACRES:
NA.22

assay

98%

form

solid

optical activity

[α]22/D −355°, c = 3.7 in chloroform

mp

215-219 °C (lit.)

functional group

ether

SMILES string

C1[C@H]2OC(CC3=N[C@@H]4[C@H](Cc5ccccc45)O3)=N[C@@H]2c6ccccc16

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

InChI key

BDHSVQLSNIGJNC-JYWFKMLOSA-N

Application

(3aS,3′aS,8aR,8′aR)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] can be used as a chiral ligand:
  • In the preparation of oxazole α-hydroxy esters through intermolecular Alder-Ene reaction.[1]
  • In the atom transfer radical polymerization reactions of methyl methacrylate.[2]
  • In the copper-catalyzed synthesis of isoxazolidine derivatives by reacting nitrone with α,β-unsaturated acyl phosphonate.[3]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
10027CH
04405CH
14115AR
09205LO

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Sequential Au/Cu Catalysis: A Two Catalyst One-Pot Protocol for the Enantioselective Synthesis of Oxazole ?-Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder-Ene Reaction
Nalivela KS, et al.
Advanced Synthesis & Catalysis, 360(11), 2183-2190 (2018)
Highly Efficient Atom Transfer Radical Polymerization System Based on the SaBOX/Copper Catalyst
Chen Z, et al.
Macromolecules, 52(24), 9792?9798-9792?9798 (2019)
Cu (II)-catalyzed enantioselective 1, 3-dipolar cycloaddition of nitrones with α,β-unsaturated acyl phosphonates
Xie L, et al.
Tetrahedron, 73(20), 2923-2930 (2017)
Sequential Au/Cu Catalysis: A Two Catalyst One-Pot Protocol for the Enantioselective Synthesis of Oxazole ?-Hydroxy Esters via Intramolecular Cyclization/Intermolecular Alder-Ene Reaction
Nalivela KS, et al.
advanced synthesis and catalysis, 360(11), 2183-2190 (2018)

Articles

C2-symmetric chiral bisoxazolines (BOX) ligands

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

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