137845-37-5

Basic information

• Product Name: Benzenesulfonamide, 4-methyl-N-(3-phenyl-2-propenylidene)-, (E,E)-
• CAS NO: 137845-37-5
• Molecular Formula: C16H15NO2S
• Molecular Weight: 285.367
• Mol File: 137845-37-5.mol
• Article Data: 43

Chemical Properties

• CAS DataBase Reference: Benzenesulfonamide, 4-methyl-N-(3-phenyl-2-propenylidene)-, (E,E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-methyl-N-(3-phenyl-2-propenylidene)-, (E,E)-(137845-37-5)
• EPA Substance Registry System: Benzenesulfonamide, 4-methyl-N-(3-phenyl-2-propenylidene)-, (E,E)-(137845-37-5)

Safety Data

• Hazardous Substances Data: 137845-37-5(Hazardous Substances Data)

Upstream product

• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 70-55-3 toluene-4-sulfonamide 
• 104-55-2 3-phenyl-propenal 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 6873-55-8 p-tolylsulfinyl amide 
• 14371-10-9 (E)-3-phenylpropenal 
• 120419-99-0 4-phenyl-1-trimethylsilyl-1-azabuta-1,3-diene 
• 98-59-9 p-toluenesulfonyl chloride 
• 127-65-1 chloroamine-T 
• 156462-94-1 2-((E)-Styryl)-naphtho[1,8-de][1,3]dithiine 
• 104-54-1 3-Phenylpropenol 
• 133039-38-0 tris(4-methylphenyl)bismuthane tosylimide 
• 163926-87-2 4-Methyl-N-[2-((E)-styryl)-1λ⁴-naphtho[1,8-de][1,3]dithiin-(1E)-ylidene]-benzenesulfonamide 

Downstream Products

• 233770-16-6 (E)-N-(4,4'-diethoxy-1-styrylbut-2-ynyl)-4-toluenesulfonamide 
• 678196-02-6 4-methyl-1-[2-(S_R)(4-methylphenylsulfonamido)-4-phenyl-(2R,3E)-3-butenylsulfinyl]benzene 
• 497-89-2 2-[1-methyl-(2S)-piperidin-2-yl]-1-phenyl-(1R)-ethan-1-ol 
• 495-47-6 1-phenyl-2-[(2S)-piperidin-2-yl]-(1R)-ethan-1-ol 
• 384835-42-1 (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylprop-1-yl)dodecanamide 
• 678196-17-3 2-[(2R)-1,2,5,6-tetrahydropyridin-2-yl]-1-phenyl-(1R)-ethan-1-ol 
• 678196-16-2 2-[1-(4-methylphenylsulfonyl)-(2R)-1,2,5,6-tetrahydropyridin-2-yl]-1-phenyl-(1R)-ethyl acetate 
• 678196-14-0 Acetic acid (1R,3R)-3-[but-3-enyl-(toluene-4-sulfonyl)-amino]-4-oxo-1-phenyl-butyl ester 
• 678196-04-8 N-[3-hydroxy-1-(S_S)(4-methylphenylsulfinylmethyl)-3-phenyl-(1R,3R)-propyl]-4-methyl-1-benzenesulfonamide 
• 678196-03-7 N-[2-bromo-3-hydroxy-1-(S_S)(4-methylphenylsulfinylmethyl)-3-phenyl-(1S,2R,3S)-propyl]-4-methyl-1-benzenesulfonamide 
• 678196-11-7 4-(S_S)(4-methylphenylsulfinyl)-3-(4-methylphenylsulfonamido)-1-phenyl-(1R,3R)-butyl acetate 
• 678196-15-1 ethyl 4-[N-(3-butenyl)-(4-methylphenyl)sulfonamido]-6-acetoxy-6-phenyl-(E,4R,6R)-2-hexenoate 
• 678196-12-8 3-[N-(3-butenyl)-(4-methylphenyl)sulfonamido]-4-(S_S)(4-methylphenylsulfinyl)-1-phenyl-(1R,3R)-butyl acetate 
• 678196-05-9 1-[4-tert-butyldiphenylsilyloxy-2-(4-methylphenylsulfonamido)-4-phenyl-(2R,4R)-butyl-(S_S)-sulfinyl]-4-methylbenzene 

Relevant articles and documents

Decarboxylative Mannich Reactions with Substituted Malonic Acid Half-Oxyesters

The decarboxylative Mannich reaction between imines and substituted malonic acids half-oxyesters (SMAHOs) has been developed using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an organocatalyst. The reaction proceeds under simple reaction conditions and toler

A Unified Explanation for Chemoselectivity and Stereospecificity of Ni-Catalyzed Kumada and Cross-Electrophile Coupling Reactions of Benzylic Ethers: A Combined Computational and Experimental Study

Ni-catalyzed C(sp3)-O bond activation provides a useful approach to synthesize enantioenriched products from readily available enantioenriched benzylic alcohol derivatives. The control of stereospecificity is key to the success of these transformations. To elucidate the reversed stereospecificity and chemoselectivity of Ni-catalyzed Kumada and cross-electrophile coupling reactions with benzylic ethers, a combined computational and experimental study is performed to reach a unified mechanistic understanding. Kumada coupling proceeds via a classic cross-coupling mechanism. Initial rate-determining oxidative addition occurs with stereoinversion of the benzylic stereogenic center. Subsequent transmetalation with the Grignard reagent and syn-reductive elimination produce the Kumada coupling product with overall stereoinversion at the benzylic position. The cross-electrophile coupling reaction initiates with the same benzylic C-O bond cleavage and transmetalation to form a common benzylnickel intermediate. However, the presence of the tethered alkyl chloride allows a facile intramolecular SN2 attack by the benzylnickel moiety. This step circumvents the competing Kumada coupling, leading to the excellent chemoselectivity of cross-electrophile coupling. These mechanisms account for the observed stereospecificity of the Kumada and cross-electrophile couplings, providing a rationale for double inversion of the benzylic stereogenic center in cross-electrophile coupling. The improved mechanistic understanding will enable design of stereoselective transformations involving Ni-catalyzed C(sp3)-O bond activation.