32121-04-3

Basic information

• Product Name: N-cinnamyl-4-methylbenzenesulfonamide
• Synonyms: N-cinnamyl-4-methylbenzenesulfonamide
• CAS NO: 32121-04-3
• Molecular Weight: 287.382
• Mol File: 32121-04-3.mol
• Article Data: 62

Chemical Properties

• CAS DataBase Reference: N-cinnamyl-4-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-cinnamyl-4-methylbenzenesulfonamide(32121-04-3)
• EPA Substance Registry System: N-cinnamyl-4-methylbenzenesulfonamide(32121-04-3)

Safety Data

• Hazardous Substances Data: 32121-04-3(Hazardous Substances Data)

Upstream product

• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 873-66-5 1-propenylbenzene 
• 851-06-9 bis(p-toluenesulfonyl) sulfur diimide 
• 100-39-0 benzyl bromide 
• 136573-35-8 N-<2-(Phenylseleno)ethyl>-p-toluenesulfonamide 
• 591-50-4 iodobenzene 
• 18303-03-2 prop-2-en-1-yl (4-methylbenzene-1-sulfonyl)carbamate 
• 32120-97-1 ethyl cinnamyl(tosyl)carbamate 
• 5044-52-0 vinyltriphenylphosphonium bromide 
• 100-52-7 benzaldehyde 
• 70-55-3 toluene-4-sulfonamide 
• 4392-24-9 Cinnamyl bromide 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 52925-24-3 N,N-dicinnamyl-N-tosylamine 
• 116043-35-7 4-methyl-N-[(2E)-3-phenyl-2-propenyl]-N-methylbenzenesulfonamide 
• 40132-64-7 (E)-(4,4-dimethylpent-1-en-1-yl)benzene 
• 20442-73-3 (1E)-3-(4-methoxyphenyl)-1-phenylpropene 
• 75437-07-9 [(1E)-4-methyl-1-penten-1-yl]benzene 
• 89373-21-7 (E)-trimethyl(4-phenylbut-3-enyl)silane 
• 1333226-20-2 C₂₃H₂₃NO₄S₂ 
• 1330067-09-8 (R,E)-methyl 2-((N-cinnamyl-4-methylphenylsulfonamido)(p-tolyl)-methyl)acrylate 
• 5848-57-7 4-methyl-N-[(2E)-3-phenylprop-2-en-1-yl]benzene-1-sulfonamide 
• 5435-02-9 4-methyl-N-(3-phenylpropyl)benzenesulfonamide 

Relevant articles and documents

High Chirality Transfer in Chiral Selenimides via Sigmatropic Rearrangement

The imination of chiral cinnamyl 2-(1-dimethylaminoethyl)ferrocenyl selenides with phenyliodinane and chloramine-T affords the corresponding chiral allylic amines via sigmatropic rearrangement of the selenimide intermediates with up to 87percent ee, highly diastereoselective imination of selenides and highly stereospecific sigmatropic rearrangement being shown.

Palladium-Catalyzed Regioselective and Stereospecific Ring-Opening Suzuki-Miyaura Arylative Cross-Coupling of 2-Arylazetidines with Arylboronic Acids

We have developed a palladium-catalyzed regioselective and enantiospecific ring-opening Suzuki–Miyaura arylative cross-coupling of N-tosyl-2-arylazetidines to give enantioenriched 3,3-diarylpropylamines. This reaction represents an example of transition-metal-catalyzed ring-opening cross-coupling using azetidines as a non-classical alkyl electrophile. Density functional theory rationalized the mechanism of the full catalytic cycle, which consists of the selectivity-determining ring opening of the azetidine, reaction with water, rate-determining transmetalation, and reductive elimination. Transition states of the selectivity-determining ring-opening step were systematically determined by the multi-component artificial force induced reaction (MC-AFIR) method to explain the regioselectivity of the reaction. (Figure presented.).

Lewis Base-Catalyzed Amino-Acylation of Arylallenes via C-N Bond Cleavage: Reaction Development and Mechanistic Studies

Lewis base-catalyzed transformations of allenes have received much attention over the last decades. However, this type of reaction has so far been limited to activated allenes bearing an electron-withdrawing group. On the other hand, cleavage of an amide C-N bond to forge other chemical bonds has been widely reported but restricted to low atom economy due to the waste of the amine moiety of amides. We initiated a project of metal-catalyzed amino-acylation of allenes via cleavage of amide C-N bonds. Surprisingly, an amino-acylation of weakly activated aryl allenes was discovered via Lewis base catalysis, providing 2-methyl-3-aroylindole products, "privileged structures"in drug discovery. This is a unique example of Lewis base catalysis of weakly activated allenes, which was not reported yet. Extensive experimental and computational studies have been conducted to provide insight into the reaction mechanism. The nucleophilic addition of Lewis base catalyst to aryl allene is the rate-limiting step. A challenging [1,3]-proton transfer is realized by nitrogen anion intermediate assisted sequential [1,4]- and [1,6]-proton transfer in the reaction pathway.