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53953

Hydroquinidine 9-phenanthryl ether

Name: Hydroquinidine 9-phenanthryl ether
Brand: SIAL

technical, ≥94% (sum of enantiomers, HPLC)

Synonym(s):

O-(9-Phenanthryl)hydroquinidine

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₃₄N₂O₂

CAS Number:

135042-88-5

Molecular Weight:

502.65

UNSPSC Code:

12352000

Beilstein/REAXYS Number:

4848701

MDL number:

MFCD00134564

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grade

technical

assay

≥94% (sum of enantiomers, HPLC)

optical activity

[α]20/D −320±10°, c = 1% in ethanol

mp

112 °C (dec.) (lit.)

SMILES string

CC[C@@H]1CN2CC[C@H]1C[C@@H]2[C@@H](Oc3cc4ccccc4c5ccccc35)c6ccnc7ccc(OC)cc67

InChI

1S/C34H34N2O2/c1-3-22-21-36-17-15-23(22)18-32(36)34(29-14-16-35-31-13-12-25(37-2)20-30(29)31)38-33-19-24-8-4-5-9-26(24)27-10-6-7-11-28(27)33/h4-14,16,19-20,22-23,32,34H,3,15,17-18,21H2,1-2H3/t22-,23+,32-,34+/m1/s1

InChI key

TWOVHUYOMTVDRB-FVSKFNOUSA-N

Other Notes

Catalyst used in the asymmetric dihydroxylation of olefins; it gives improved diastereoselectivity compared to the 4-chlorobenzoate, especially for α,β-unsaturated esters

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R. Oi et al.

Tetrahedron Letters, 33, 2095-2095 (1992)

K.B. Sharpless et al.

The Journal of Organic Chemistry, 56, 4585-4585 (1991)

H.C. Kolb et al.

Chemical Reviews, 94, 2483-2483 (1994)

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