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334162

Sigma-Aldrich

trans-1,2-Bis(phenylsulfonyl)ethylene

98%

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About This Item

Linear Formula:
C6H5SO2CH=CHSO2C6H5
CAS Number:
963-16-6
Molecular Weight:
308.37
Beilstein:
2334889
MDL number:
MFCD00066528
UNSPSC Code:
12352100
PubChem Substance ID:
24860060
NACRES:
NA.22

Assay

98%

mp

221-223 °C (lit.)

SMILES string

O=S(=O)(\C=C\S(=O)(=O)c1ccccc1)c2ccccc2

InChI

1S/C14H12O4S2/c15-19(16,13-7-3-1-4-8-13)11-12-20(17,18)14-9-5-2-6-10-14/h1-12H/b12-11+

InChI key

YGBXMKGCEHIWMO-VAWYXSNFSA-N

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General description

Chiral BINAP-AuTFA- and chiral BINAP-AgTFA (TFA = trifluoroacetate anion) -promoted catalytic enantioselective 1,3-dipolar cycloadditions of iminoglycinates with trans-1,2-bis(phenylsulfonyl)ethylene were studied.

Application

trans-1,2-Bis(phenylsulfonyl)ethylene was used in total synthesis of (+)-7-deoxypancratistatin.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Binap-gold (I) trifluoroacetate as a bifunctional catalyst for the synthesis of chiral prolines through 1, 3-dipolar cycloaddition of azomethine ylides.
Martin-Rodriguez M, et al.
Tetrahedron Asymmetry, 21(9), 1184-1186 (2010)
J L Aceña et al.
Organic letters, 2(23), 3683-3686 (2000-11-14)
A new total synthesis of (+)-7-deoxypancratistatin 1 has been accomplished in 19 steps (8% overall yield) from two readly available compounds, furan and trans-1,2-bis(phenylsulfonyl)ethylene.

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