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(S)-VAPOL

Name: (<I>S</I>)-VAPOL
Brand: ALDRICH

97%

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Synonym(s):

(S)-2,2′-Diphenyl-(4-biphenanthrol)

Empirical Formula (Hill Notation):

C₄₀H₂₆O₂

CAS Number:

147702-15-6

Molecular Weight:

538.63

EC Number:

200-838-9

MDL number:

MFCD11617354

PubChem Substance ID:

24885273

NACRES:

NA.22

Quality Level

100

Assay

97%

form

solid

optical activity

[α]20/D 128°, c = 1 in chloroform

mp

185-191 °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

Chiral Catalysts & Ligands

Application

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

Pictograms

GHS07,GHS08

Signal Word

Warning

Hazard Statements

H315 - H319 - H351

Precautionary Statements

P202 - P264 - P280 - P302 + P352 - P305 + P351 + P338 - P308 + P313

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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A dual chromophore sensor for the detection of amines, diols, hydroxy acids, and amino alcohols.

Mariia Pushina et al.

Chemical communications (Cambridge, England), 55(31), 4495-4498 (2019-03-29)

The determination of enantiomeric excess (ee) in various groups of chiral compounds, namely amines, amino alcohols, diols, and hydroxy acids is performed using a dual chromophore FRET/PET based sensor ensemble. The sensing ensemble utilizes fluorescence changes from two chromophores (indicators)

Highly enantioselective deracemization of linear and vaulted biaryl ligands.

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

Bao. J. et al.

Journal of the American Chemical Society, 118, 3392-3392 (1996)

New synthesis of vaulted biaryl ligands via the Snieckus phenol synthesis.

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.