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673986

Sigma-Aldrich

2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine

≥94%

Synonym(s):

(3aR,3′aR,8aS,8′aS)-2,2′-(2,6-Pyridinediyl)bis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole, (3aR,8aS)-in-pybox

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About This Item

Empirical Formula (Hill Notation):
C25H19N3O2
CAS Number:
357209-32-6
Molecular Weight:
393.44
MDL number:
MFCD09265074
UNSPSC Code:
12352005
PubChem Substance ID:
24885191
NACRES:
NA.22

Assay

≥94%

form

solid

optical activity

[α]20/D +386°, c = 1 in methylene chloride(lit.)

mp

284 °C (dec.)

SMILES string

C1[C@@H]2OC(=N[C@@H]2c3ccccc13)c4cccc(n4)C5=N[C@H]6[C@H](Cc7ccccc67)O5

InChI

1S/C25H19N3O2/c1-3-8-16-14(6-1)12-20-22(16)27-24(29-20)18-10-5-11-19(26-18)25-28-23-17-9-4-2-7-15(17)13-21(23)30-25/h1-11,20-23H,12-13H2/t20-,21-,22+,23+/m0/s1

InChI key

BZSJUFJXCHHRHW-MYDTUXCISA-N

Application

Catalytic ligand used for:
  • [3+2] cycloaddition of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage
  • Enantioselective Mukaiyama-aldol reactions
  • Enantioselective carbonyl-ene reactions
  • Cu(I)-catalyzed asymmetric alkynylation of imino esters with terminal alkynes
  • Asymmetric three-component coupling reactions catalyzed by a Cu/pybox complex
  • Enantioselective Diels-Alder reaction
  • Ni-catalyzed cross-coupling reactions

Hazard Statements

H413

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Articles

PYBOX

The PYBOX ligand, consisting of a pyridine ring flanked by two oxazoline groups, was introduced in 1989 by Nishiyama.

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