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Merck

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號碼:
分類程式碼代碼:
12352005
PubChem物質ID:
NACRES:
NA.22

化驗

97%

形狀

solid

光學活性

[α]20/D +310°, c = 1 in chloroform

mp

200-204 °C

SMILES 字串

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 密鑰

NDTDVKKGYBULHF-UHFFFAOYSA-N

應用

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.

象形圖

CorrosionExclamation mark

訊號詞

Danger

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves


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其他客户在看

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)
An efficient enantioselective synthesis of florfenicol via asymmetric aziridination.
Wang Z, et al.
Tetrahedron, 67(47), 9199-9203 (2011)
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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