(E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide

Base Information

• Chemical Name: (E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide
• CAS No.: 186249-75-2
• Molecular Formula: C₁₃H₁₇NOS
• Molecular Weight: 235.35
• Mol file: 186249-75-2.mol

Synonyms:(E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide

Chemical Property of (E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide

There total 3 articles about (E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide 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: 92.0%

(E)-3-phenylpropenal (14371-10-9) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide (186249-75-2)

Guidance literature:

With Triisopropyl borate; at 60 ℃; for 24h;

DOI:10.1016/j.tetlet.2016.03.063

Reference yield: 68.0%

3-phenyl-propenal (104-55-2) + (S)-2-methylpropane-2-sulfinamide (343338-28-3) → (E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide (186249-75-2)

Guidance literature:

With pyridinium p-toluenesulfonate; magnesium sulfate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/ol800478q

Reference yield:

(E)-3-phenylpropenal (14371-10-9) + tert-butylsulfinyl chloride (31562-43-3) → (E)-(S)-2-methyl-propane-2-sulfinic acid [(E)-3-phenyl-prop-2-enylidene]-amide (186249-75-2)

Guidance literature:

With 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; triethylamine; cesium fluoride; lithium hexamethyldisilazane; Yield given. Multistep reaction; 1.) toluene, 0 deg C, 2.) THF, RT, 2.) THF, RT;

DOI:10.1016/S0957-4166(96)00448-X

upstream raw materials:

(E)-3-phenylpropenal

tert-butylsulfinyl chloride

(S)-2-methylpropane-2-sulfinamide

3-phenyl-propenal

Downstream raw materials:

C₁₉H₂₅NOS

(S)-2-methyl-propane-2-sulfinic acid ((E)-(R)-1-(R)-cyclohexa-2,4-dienyl-3-phenylallyl)-amide

Refernces

• 1、 Visco, Michael D.,Reeves, Jonathan T.,Marsini, Maurice A.,Volchkov, Ivan,Busacca, Carl A.,Mattson, Anita E.,Senanayake, Chris H.. "Triisopropyl borate mediated N-sulfinyl imine formation". supporting information. p. 1903 - 1905. Retrieved 2016/04/19.
• 2、 Maji, Modhu Sudan,Froehlich, Roland,Studer, Armido. "Desymmetrization of metallated cyclohexadienes with chiral N-tert-butanesulfinyl imines". supporting information; experimental part. p. 1847 - 1850. Retrieved 2009/04/10.