468037
cis-1,4-Diacetoxy-2-butene
95%
Sinonimo/i:
cis-2-Butene-1,4-diol diacetate
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About This Item
Formula condensata:
CH3CO2CH2CH=CHCH2O2CCH3
Numero CAS:
Peso molecolare:
172.18
Numero MDL:
Codice UNSPSC:
12352100
ID PubChem:
NACRES:
NA.22
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Livello qualitativo
Saggio
95%
Indice di rifrazione
n20/D 1.443 (lit.)
P. ebollizione
120-121 °C/18 mmHg (lit.)
Densità
1.08 g/mL at 25 °C (lit.)
Gruppo funzionale
ester
Stringa SMILE
[H]\C(COC(C)=O)=C(/[H])COC(C)=O
InChI
1S/C8H12O4/c1-7(9)11-5-3-4-6-12-8(2)10/h3-4H,5-6H2,1-2H3/b4-3-
VZUAUHWZIKOMFC-ARJAWSKDSA-N
Descrizione generale
cis-1,4-Diacetoxy-2-butene is an ester. Ruthenium olefin metathesis catalysts having cyclic (alkyl)(amino)carbenes effectively catalyzes the cross-metathesis of cis-1,4-diacetoxy-2-butene with allylbenzene. cis-1,4-Diacetoxy-2-butene on pyrolysis affords 1-acetoxy-1,3-butadiene, a diacetate and an isomeric 1,2-diacetoxy-3-butene. Mechanism of pyrolysis has been investigated.
Applicazioni
cis-1,4-Diacetoxy-2-butene may be used in the preparation of hindered Diels-Alder adducts. It may be used for the synthesis of 1,2,3,4-tetrahydro-2-vinylquinoxalines, via Palladium-catalyzed tandem allylation of 1,2-phenylenediamines.
Avvertenze
Warning
Indicazioni di pericolo
Consigli di prudenza
Classi di pericolo
Skin Irrit. 2
Codice della classe di stoccaggio
10 - Combustible liquids
Classe di pericolosità dell'acqua (WGK)
WGK 3
Punto d’infiammabilità (°F)
235.4 °F - closed cup
Punto d’infiammabilità (°C)
113 °C - closed cup
Dispositivi di protezione individuale
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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Kerstin Rosmarion et al.
Applied spectroscopy, 59(3), 366-375 (2005-05-20)
Hindered Diels-Alder adducts have been prepared from 3,6-dibromophencyclone, 2, with cis-1,4-diacetoxy-2-butene, 3; cis-2-butene-1,4-diol, 4; and N-benzylmaleimide, 5. The adduct from the parent phencyclone, 1, with N-benzylmaleimide was prepared for comparison. One- and two-dimensional (1D and 2D) proton and carbon-13 NMR
Pyrolysis of Esters. V. Mechanism of 1, 4-Elimination1.
Bailey WJ and BARCLAY Jr R.
The Journal of Organic Chemistry, 21(3), 328-331 (1956)
Donde R Anderson et al.
Organometallics, 27(4), 563-566 (2008-06-28)
The evaluation of ruthenium olefin metathesis catalysts 4-6 bearing cyclic (alkyl)(amino)carbenes (CAACs) in the cross-metathesis of cis-1,4-diacetoxy-2-butene (7) with allylbenzene (8) and the ethenolysis of methyl oleate (11) is reported. Relative to most NHC-substituted complexes, CAAC-substituted catalysts exhibit lower E/Z
Palladium-catalyzed tandem allylation of 1, 2-phenylenediamines with cis-1, 4-diacetoxy-2-butene.
Yang SC, et al.
Tetrahedron Letters, 45(25), 4951-4954 (2004)
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