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Merck
CN

676098

Sigma-Aldrich

(S)-VANOL

97%

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别名:
(2S)-(-)-3,3′-二苯基-[2,2′-联二萘]-1,1′-二醇, (S)-3,3′-二苯基-2,2′-二-(1-萘酚)
经验公式(希尔记法):
C32H22O2
分子量:
438.52
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22

质量水平

检测方案

97%

旋光性

[α]20/D -314°, c = 1 in chloroform

mp

199-203 °C

SMILES字符串

Oc1c(c(cc2ccccc12)-c3ccccc3)-c4c(O)c5ccccc5cc4-c6ccccc6

InChI

1S/C32H22O2/c33-31-25-17-9-7-15-23(25)19-27(21-11-3-1-4-12-21)29(31)30-28(22-13-5-2-6-14-22)20-24-16-8-10-18-26(24)32(30)34/h1-20,33-34H

InChI key

NDTDVKKGYBULHF-UHFFFAOYSA-N

应用

(S)-VANOL 是一种拱形联芳基配体,可用于合成配位配合物,例如(dppe)Pt(S-VANOL)[dppe =双(二苯基膦基)乙烷]和(S,S-chiraphos)Pt (S-VANOL)[Chiraphos=2,3-双(二苯基膦基)丁烷]。
VANOL 已被证明是催化不对称 Diels-Alder、亚胺羟醛和叠氮化反应的出色配体。

象形图

CorrosionExclamation mark

警示用语:

Danger

危险分类

Aquatic Chronic 4 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

靶器官

Respiratory system

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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Synthesis and characterization of chiral diphosphine platinum (II) VANOL and VAPOL complexes.
Becker JJ, et al.
Organometallics, 22(16), 3245-3249 (2003)
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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The research areas of interest to the Wulff group include enantioselective catalysis, mechanisms of asymmetric catalysis, macromolecular chemistry, Fischer carbene complexes in organic synthesis and the total synthesis of natural products.

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