132330-42-8

Basic information

• Product Name: N-cinnamyl-4-methyl-N-(2-propynyl)benzenesulfonamide
• Synonyms: N-cinnamyl-4-methyl-N-(2-propynyl)benzenesulfonamide
• CAS NO: 132330-42-8
• Molecular Formula: C₁₉H₁₉NO₂S
• Molecular Weight: 325.42466
• Mol File: 132330-42-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-cinnamyl-4-methyl-N-(2-propynyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-cinnamyl-4-methyl-N-(2-propynyl)benzenesulfonamide(132330-42-8)
• EPA Substance Registry System: N-cinnamyl-4-methyl-N-(2-propynyl)benzenesulfonamide(132330-42-8)

Safety Data

• Hazardous Substances Data: 132330-42-8(Hazardous Substances Data)

Upstream product

• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4392-24-9 Cinnamyl bromide 
• 98-59-9 p-toluenesulfonyl chloride 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 189031-66-1 N-(tert-butoxycarbonyl)-4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 189031-61-6 (N,N)-tert-butoxycarbonyl-cinnamyl-p-tosylamine 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 5848-57-7 4-methyl-N-[(2E)-3-phenylprop-2-en-1-yl]benzene-1-sulfonamide 
• 106-96-7 propargyl bromide 

Downstream Products

• 454431-91-5 Carbonic acid methyl ester 4-[((Z)-3-phenyl-allyl)-(toluene-4-sulfonyl)-amino]-but-2-ynyl ester 
• 144365-91-3 3-((E)-2-Ethoxy-propenyl)-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole 
• 1192778-05-4 7-phenyl-3-tosyl-3-azabicyclo[4.1.0]hept-4-ene 

Relevant articles and documents

Selective ruthenium-catalyzed transformations of enynes with diazoalkanes into alkenylbicyclo[3.1.0]hexanes

Reaction of a variety of C≡CH bond-containing 1,6-enynes with N 2CHSiMe3 in the presence of RuCl(COD)Cp* as catalyst precursor leads, at room temperature, to the general formation of alkenylbicyclo[3.1.0]hexanes with high Z-stereosel

Copper-catalysed hydroamination of N-allenylsulfonamides: The key role of ancillary coordinating groups

A copper-catalysed hydroamination reaction of N-allenylsulfonamides with amines has been developed through a rational approach based on mechanistic studies. The reaction is promoted by a simple copper(I) catalyst and proceeds at room temperature with complete regioselectivity and excellent stereoselectivity towards linear (E)-N-(3-aminoprop-1-enyl)sulfonamides. Density Functional Theory (DFT) studies allow interpreting the key role of unsaturated substituents on nitrogen as ancillary coordinating moieties for the copper catalyst.

Complementary Reactivity of 1,6-Enynes with All-Metal Aromatic Trinuclear Complexes and Carboxylic Acids

The distinct reactivity of 1,6-enynes in the presence of a trinuclear metal complex activated by a carboxylic acid is presented. The triplatinum catalyst enables the cyclization of the substrate and subsequent incorporation of a nucleophile in the final product. In contrast, sequential cyclization/double bond shift occurs under analogous conditions in the presence of the corresponding tripalladium complex.

A New Approach to Non-Coordinating Anions: Lewis Acid Enhancement of Porphyrin Metal Centers in a Zwitterionic Metal-Organic Framework

We describe a new strategy to generate non-coordinating anions using zwitterionic metal-organic frameworks (MOFs). By assembly of anionic inorganic secondary building blocks (SBUs) ([In(CO2)4]-) with cationic metalloporphyrin-based organic linkers, we prepared zwitterionic MOFs in which the complete internal charge separation effectively prevents the potential binding of the counteranion to the cationic metal center. We demonstrate the enhanced Lewis acidity of MnIII- and FeIII-porphyrins in the zwitterionic MOFs in three representative electrocyclization reactions: [2 + 1] cycloisomerization of enynes, [3 + 2] cycloaddition of aziridines and alkenes, and [4 + 2] hetero-Diels-Alder cycloaddition of aldehydes with dienes. This work paves a new way to design functional MOFs for tunable chemical catalysis.

SYNTHESIS, STRUCTURE AND USE OF FUNCTIONALIZED NAPHTHALENES

Methods for the synthesis and use of functionalized, substituted naphthalenes are described. The functionalized, substituted naphthalenes display useful properties including liquid crystals and fluorescence properties, such as solvatochromatic fluorescenc

Titanium(IV) chloride-mediated carbocyclization of 1,6-Enynes: Selective synthesis of 3-Azabicyclo[3.1.0]hexanes and functionalized allenes by controlling the reaction temperature

1,6-Enynes can be transformed into 3-azabicyclo[3.1.0]hexanes and functionalized allenes in moderate to good yields along with moderate to high diastereoselectivities by controlling the reaction temperature in the presence of titanium(IV) chloride. A plausible mechanism is proposed. 1,6-Enynes can be transformed into 3-azabicyclo[3.1.0]hexanes and functionalized allenes respectively in moderate to goodyields along with moderate to high diastereoselectivities by controlling the reaction temperature in the presence of titanium(IV) chloride. A plausible mechanism is proposed.

(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl 2]2}: A novel efficient catalyst for the cycloisomerizations of homopropargylic diols and N-tethered enynes

(Pentamethylcyclopentadienyl)iridium dichloride dimer {[IrCp*Cl 2]2}-catalyzed hydroalkoxylation of bis-homopropargylic alcohols provides an efficient access to dioxabicyclo[2.2.1]ketals. The cycloisomerizations proceed under mild conditions, with low catalytic loadings and short reaction times. This new protocol involving an Ir(III) catalyst also promoted the cycloisomerization of nitrogen-tethered 1,6-enynes to give azabicyclo[4.1.0]heptenes, enhancing the synthetic potential of our method. Copyright

Enyne metathesis-oxidation sequence for the synthesis of 2-phosphono pyrroles: Proof of the "yne-then-ene" pathway

A new tandem reaction sequence has been developed for the synthesis of 2-phosphono pyrroles. The sequence consists of ring-closing enyne metathesis of a substituted aminophosphonate, containing a terminal alkyne and an internal alkene, in combination with

Gold(l)-catalyzed cascade cyclization reaction: Highly regio- and diastereoselective intermodular addition of water and alcohols to epoxy alkynes

We have developed a novel access to ketal skeletons through a highly regio- and diastereoselective intermolecular addition of water and alcohols to alkynyl epoxides catalyzed by goid(l). This procedure involves a domino three-membered ring-opening, 6-exo-

On the mechanism of carbohydroxypalladation of enynes. Additional insights on the cyclization of enynes with electrophilic metal complexes

Different mechanisms have been proposed for the cyclization of enynes catalyzed by electrophilic metal halides or complexes. We present evidence to indicate that the previously reported "carbohydroxypalladation" and the "hydroxycyclization catalyzed by PtII" are closely related reactions. Thus, palladium complexes formed in situ from PdCl2 and trisulfonated phosphane TPPTS or cyclic phosphite P(OCH2)3CEt as the ligands catalyze the methoxy- or hydroxycyclization of enynes with selectivities similar to those observed with PtII complexes. Deuteration studies indicate that activation of the alkyne by PdII promotes an anti-addition of the alkene. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.