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Merck
CN

464155

Sigma-Aldrich

[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
分子量:
330.38
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22

检测方案

98%

旋光性

[α]22/D +353°, c = 3.7 in chloroform

mp

204-206 °C (lit.)

SMILES字符串

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

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

InChI key

BDHSVQLSNIGJNC-ZCLUNYJNSA-N

应用

[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.

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

Eye Irrit. 2 - 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


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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

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。

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

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