trans-1,2-Bis(phenylsulfonyl)ethylene

Base Information

• Chemical Name: trans-1,2-Bis(phenylsulfonyl)ethylene
• CAS No.: 963-16-6
• Molecular Formula: C14H12 O4 S2
• Molecular Weight: 308.379
• Hs Code.: 29041000
• European Community (EC) Number: 626-405-8
• NSC Number: 202471
• DSSTox Substance ID: DTXSID901225042
• Nikkaji Number: J181.734E,J323.450I
• Mol file: 963-16-6.mol

Synonyms:trans-1,2-Bis(phenylsulfonyl)ethylene;963-16-6;[(E)-2-(benzenesulfonyl)ethenyl]sulfonylbenzene;(E)-1,2-Bis(phenylsulfonyl)ethene;Benzene, 1,1'-[(1E)-1,2-ethenediylbis(sulfonyl)]bis-;NSC202471;UPCMLD00WV-99;1,2-Bis(phenylsulfonyl)ethene;SCHEMBL1344338;DTXSID901225042;trans-1,2-diphenylsulfonylethylene;Z-1,2-Bis(phenylsulfonyl)ethylene;MFCD00066528;AKOS015840622;(Z)-1,2-Bis(benzenesulfonyl)ethylene;NSC-202471;AS-65834;B1574;CS-0035489;Ethylene, 1,2-bis(phenylsulfonyl)-, (Z)-;trans-1,2-Bis(phenylsulfonyl)ethylene, 98%;W12526;[(1E)-2-(benzenesulfonyl)ethenesulfonyl]benzene;1,1'-[(E)-ethene-1,2-diyldisulfonyl]dibenzene;([(Z)-2-(Phenylsulfonyl)ethenyl]sulfonyl)benzene;1,1'-[(1E)-1,2-Ethenediylbis(sulfonyl)]bis[benzene];Benzene, 1,1'-[1,2-ethenediylbis(sulfonyl)]bis-, (Z)-;trans-1,2-Bis(phenylsulfonyl)ethylene, purum, >=98.0% (HPLC)

Chemical Property of trans-1,2-Bis(phenylsulfonyl)ethylene

Chemical Property:

• Vapor Pressure: 2.2E-11mmHg at 25°C
• Melting Point: 221-223 °C(lit.)
• Boiling Point: 545°C at 760 mmHg
• Flash Point: 363.3°C
• PSA: 85.04000
• Density: 1.355g/cm³
• LogP: 4.56700
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 308.01770121
• Heavy Atom Count: 20
• Complexity: 473

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-1,2-Bis(phenylsulfonyl)ethylene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)C=CS(=O)(=O)C2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)S(=O)(=O)/C=C/S(=O)(=O)C2=CC=CC=C2
• Uses: trans-1,2-Bis(phenylsulfonyl)ethylene was used in total synthesis of (+)-7-deoxypancratistatin. trans-1,2-Bis(phenylsulfonyl)ethylene is useful for the synthesis of dysiherbaine and neodysiherbaine A.

Technology Process of trans-1,2-Bis(phenylsulfonyl)ethylene

There total 16 articles about trans-1,2-Bis(phenylsulfonyl)ethylene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

(Z)-1,2-bis(phenylsulfonyl)ethene (963-15-5) → (E)-1,2-bis(phenylsulfonyl)ethylene (963-16-6)

Guidance literature:

iodine; In dichloromethane; Irradiation;

DOI:10.1021/jo00178a004

Reference yield: 80.0%

Phenyl-β,β-dichlorethylsulfon (3123-10-2) + sodium benzenesulfonate (873-55-2) → (E)-1,2-bis(phenylsulfonyl)ethylene (963-16-6)

Guidance literature:

In methanol; water; for 5h; Ambient temperature;

DOI:10.1055/s-1999-3416

Reference yield: 80.0%

(E)-2-chloroethenyl phenyl sulfone (38238-75-4) + sodium benzenesulfonate (873-55-2) → (E)-1,2-bis(phenylsulfonyl)ethylene (963-16-6)

Guidance literature:

In methanol; water; for 3h; Ambient temperature;

DOI:10.1055/s-1999-3416

upstream raw materials:

(E)-1,2-bis(phenylsulfanyl)ethylene

(E)-2-chloroethenyl phenyl sulfone

Benzenesulfinic acid

cis-1,2-bis-phenylsulfanyl-ethylene

Downstream raw materials:

(+/-)-trans-2,3-bis(phenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene

1-<(E)-2-(phenylsulphonyl)ethenyl>-5-(iodomethyl)-2-pyrrolidinone

C₂₁H₂₂O₆S₂

(E)-2-(n-octyloxy)-1-(phenylsulfonyl)ethylen

Refernces

Synthesis of Cyclosiphonodictyol A and Its Bis(sulfato)

10.1021/acs.joc.9b03434

The study reports the first synthesis of cyclosiphonodictyol A (11) and its bis(sulfato) derivative (12) from the commercially available lactone (+)-sclareolide (17). The synthetic sequence involves 11 steps with a global yield of 46%. Key steps include the nucleophilic attack of a hindered tertiary alkoxide, a ring-closing metathesis reaction, and the Diels-Alder cycloaddition of a dienol acetate. The synthesis begins with the conversion of (+)-sclareolide (17) to alcohol 16, which is then converted to oxy-ester 21 using bromo ester 20 as an alkylating agent. The oxepane ring is formed via ring-closing metathesis of ester 21 to give ester 22. Subsequent transformations involve the conversion of ester 22 to ketone 14, followed by the construction of the aromatic ring through a series of reactions involving trans-1,2-bis(phenylsulfonyl)ethylene and isopropenyl acetate to form cycloadducts 24, which are then converted to acetate 25 and finally to phenol 13. Phenol 13 is oxidized to quinone 26 and subsequently reduced to cyclosiphonodictyol A (11). Compound 11 is then converted to its bis(sulfato) derivative (12) through successive treatments with pyridine-sulfur trioxide and Na2CO3. The synthesized compounds exhibit similar NMR data to the natural products, confirming their structures.