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675210

Sigma-Aldrich

(R)-VAPOL

97%

Synonym(s):

(R)-2,2′-Diphenyl-3,3′-(4-biphenanthrol)

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About This Item

Empirical Formula (Hill Notation):
C40H26O2
CAS Number:
147702-16-7
Molecular Weight:
538.63
MDL number:
MFCD11617354
UNSPSC Code:
12352005
PubChem Substance ID:
24885269
NACRES:
NA.22

Quality Level

100

Assay

97%

optical activity

[α]20/D -144°, c = 1 in chloroform

mp

225-229 °C

SMILES string

Oc1c(c(cc2ccc3ccccc3c12)-c4ccccc4)-c5c(O)c6c(ccc7ccccc67)cc5-c8ccccc8

InChI

1S/C40H26O2/c41-39-35-29(21-19-27-15-7-9-17-31(27)35)23-33(25-11-3-1-4-12-25)37(39)38-34(26-13-5-2-6-14-26)24-30-22-20-28-16-8-10-18-32(28)36(30)40(38)42/h1-24,41-42H

InChI key

UFYXKDMLGBKHIC-UHFFFAOYSA-N

Related Categories

Application

VAPOL has proven to be an excellent ligand in catalytic asymmetric Diels-Alder, imine aldol, and aziridination reactions.

Signal Word

Danger

Hazard Statements

H315,H318,H335,H351

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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Bao. J. et al.
Journal of the American Chemical Society, 118, 3392-3392 (1996)
Su Yu et al.
Organic letters, 7(3), 367-369 (2005-01-28)
[reaction: see text] In an effort to develop a synthesis of the VAPOL ligand that avoids the use of a chromium carbene complex, a route was examined that involved the annulation of a naphthalene carboxamide via the method of Snieckus.
Yu Zhang et al.
Organic letters, 5(11), 1813-1816 (2003-05-24)
[reaction: see text] A copper-mediated deracemization of the vaulted biaryl ligands VANOL and VAPOL can be readily achieved in the presence of (-)-spartiene. The optimal procedure involves the in situ generation of copper(II) and leads to the reproducible formation of

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