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Merck
CN

675156

Sigma-Aldrich

(R)-VANOL

97%

别名:

(2R)-(+)-3,3′-二苯基-[2,2′-联二萘]-1,1′-二醇, (R)-3,3′-二苯基-2,2′-二-1-萘酚

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About This Item

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

方案

97%

表单

solid

旋光性

[α]20/D +310°, c = 1 in chloroform

mp

200-204 °C

官能团

phenyl

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

已证实 VANOL 是用于催化型不对称 Diels-Alder 反应、亚胺羟醛反应以及氮杂环丙化反应的绝佳配体。
(R)-VANOL is a vaulted biaryl ligand that may be used in the following processes:
  • Transformation of 3-substituted cyclobutanones to enantiopure γ-butyrolactones via asymmetric Baeyer-Villiger Reaction in the presence of an aluminum catalyst.
  • Asymmetric aziridination of N-(4-(Methylsulfonyl)benzylidene)diphenylmethanamine to form (2S,3S)-ethyl 1-benzhydryl-3-(4-(methylsulfonyl)phenyl) aziridine-2-carboxylate.
  • Conjugate addition of terminal alkynes to 2-arylidene-1,3-diketones with high enantioselectivity in the presence of diethyl zinc.

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

储存分类代码

11 - Combustible Solids

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


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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访问文档库

An efficient enantioselective synthesis of florfenicol via asymmetric aziridination.
Wang Z, et al.
Tetrahedron, 67(47), 9199-9203 (2011)
Blay G, et al.
Chemistry?A European Journal , 18(41), 12966-12969 (2012)
Vaulted biaryls: efficient ligands for the aluminum-catalyzed asymmetric Baeyer-Villiger reaction.
Bolm C, et al.
Synlett, 2004(09), 1619-1621 (2004)
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.

相关内容

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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