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Merck
CN

464155

[3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-亚甲基双[3a,8a-二氢-8H-茚并[1,2-]噁唑]

98%

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经验公式(希尔记法):
C21H18N2O2
化学文摘社编号:
分子量:
330.38
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
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产品名称

[3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-亚甲基双[3a,8a-二氢-8H-茚并[1,2-]噁唑], 98%

InChI

1S/C21H18N2O2/c1-3-7-14-12(5-1)9-16-20(14)22-18(24-16)11-19-23-21-15-8-4-2-6-13(15)10-17(21)25-19/h1-8,16-17,20-21H,9-11H2/t16-,17-,20+,21+/m0/s1

SMILES string

C1[C@@H]2OC(CC3=N[C@H]4[C@@H](Cc5ccccc45)O3)=N[C@H]2c6ccccc16

InChI key

BDHSVQLSNIGJNC-ZCLUNYJNSA-N

assay

98%

optical activity

[α]22/D +353°, c = 3.7 in chloroform

mp

204-206 °C (lit.)

functional group

ether

Quality Level

Application

[3aR-[2(3′aR*,8′aS*),3′aβ,8′aβ]]-(+)-2,2′-Methylenebis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] is a C2 symmetric chiral ligand based on bis(oxazoline) moiety, which can be used in enantioselective catalysis. It easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals. Copper complex of this chiral ligand can be utilized as a reusable catalyst in the cyclopropanation reaction between styrene and ethyl diazoacetate.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

C 2-symmetric chiral bis (oxazoline) ligands in asymmetric catalysis
Desimoni G, et al.
Chemical Reviews, 106(9), 3561-3651 (2006)
Polytopic Bis (oxazoline)-Based Ligands for the Development of Recoverable Catalytic Systems Applied to the Cyclopropanation Reaction
Garcia JI, et al.
European Journal of Organic Chemistry, 2014(7), 1531-1540 (2014)
Bolm, C.
Angewandte Chemie (International Edition in English), 30, 542-542 (1991)
Gant, T.G. Meyers, A.I.
Tetrahedron, 50, 2297-2297 (1994)
Pfaltz, A.
Accounts of Chemical Research, 26, 339-339 (1993)

商品

BOX ligand complex enhances catalytic enantioselective aziridination of styrene, with phenyl substituents proving superior over t-Bu groups.

使用络合Cu(I)OTf的BOX配体进行不对称催化苯乙烯合成氮杂环丙烷的反应,BOX配体带苯基取代基的优于具有位阻需求的叔丁(t-Bu)基团。

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