462996-06-1

Basic information

• Product Name: tert-butyl allyl[(4-methylphenyl)sulfonyl]carbamate
• Synonyms: tert-butyl allyl[(4-methylphenyl)sulfonyl]carbamate
• CAS NO: 462996-06-1
• Molecular Formula: C₁₅H₂₁NO₄S
• Molecular Weight: 311.39654
• Mol File: 462996-06-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: tert-butyl allyl[(4-methylphenyl)sulfonyl]carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl allyl[(4-methylphenyl)sulfonyl]carbamate(462996-06-1)
• EPA Substance Registry System: tert-butyl allyl[(4-methylphenyl)sulfonyl]carbamate(462996-06-1)

Safety Data

• Hazardous Substances Data: 462996-06-1(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 
• 18303-04-3 N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 

Downstream Products

• 1190988-00-1 tert-butyl 2-oxoethyl(tosyl)carbamate 
• 386750-63-6 N-allyl-N-(4-hydroxybut-2-yn-1-yl)-4-methylbenzenesulfonamide 
• 1346228-67-8 C₂₁H₂₁NO₄S 
• 594858-64-7 N-allyl-4-methyl-N-(2-methylallyl)benzenesulfonamide 
• 952688-49-2 N-allyl-N-((2E)-2-butenyl)-p-toluenesulfonamide 
• 483370-09-8 N-allyl-N-but-3-enyl-4-methyl-benzenesulfonamide 
• 50487-71-3 4-methyl-N-(2-propenyl)benzenesulfonamide 

Relevant articles and documents

Copper-Catalyzed Azide–Ynamide Cyclization to Generate α-Imino Copper Carbenes: Divergent and Enantioselective Access to Polycyclic N-Heterocycles

Here an efficient copper-catalyzed cascade cyclization of azide-ynamides via α-imino copper carbene intermediates is reported, representing the first generation of α-imino copper carbenes from alkynes. This protocol enables the practical and divergent synthesis of an array of polycyclic N-heterocycles in generally good to excellent yields with broad substrate scope and excellent diastereoselectivities. Moreover, an asymmetric azide–ynamide cyclization has been achieved with high enantioselectivities (up to 98:2 e.r.) by employing BOX-Cu complexes as chiral catalysts. Thus, this protocol constitutes the first example of an asymmetric azide–alkyne cyclization. The proposed mechanistic rationale for this cascade cyclization is further supported by theoretical calculations.

An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols

Furans, pyrroles, and thiophenes are efficiently prepared by gold-catalyzed dehydrative cyclizations of readily available, heteroatom-substituted propargyllc alcohols. The reactions are rapid, high-yielding, and procedurally simple, giving essentially pure aromatic heterocycles In minutes under open-flask conditions with catalyst loadings as low as 0.05 mol %.

Fluorous Mitsunobu reagents and reactions

A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H 4)2PPh] and new [C8F17CH2CH2C6H 4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)N=NCOOCH 2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over fluorous silica provides clean products in excellent yields. The fluorous fraction containing the oxidized phosphine oxide and the reduced hydrazide can be readily separated and the starting reagents can be regenerated by appropriate redox reactions in high yield for reuse.