260967-06-4

Basic information

• Product Name: O-benzyl N-(Z)-prop-1-en-1-ylcarbamate
• Synonyms: O-benzyl N-(Z)-prop-1-en-1-ylcarbamate
• CAS NO: 260967-06-4
• Molecular Weight: 191.23
• Mol File: 260967-06-4.mol

Chemical Properties

• CAS DataBase Reference: O-benzyl N-(Z)-prop-1-en-1-ylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: O-benzyl N-(Z)-prop-1-en-1-ylcarbamate(260967-06-4)
• EPA Substance Registry System: O-benzyl N-(Z)-prop-1-en-1-ylcarbamate(260967-06-4)

Safety Data

• Hazardous Substances Data: 260967-06-4(Hazardous Substances Data)

Upstream product

• 621-84-1 O-benzyl carbamate 
• 5041-33-8 N-(Benzyloxycarbonyl)allylamine 
• 20395-87-3 2-(N-benzyloxycarbonylamino)butyric acid 

Relevant articles and documents

Chiral Alkyl Amine Synthesis via Catalytic Enantioselective Hydroalkylation of Enecarbamates

Chiral alkyl amines are omnipresent as bioactive molecules and synthetic intermediates. The catalytic and enantioselective synthesis of alkyl amines from readily accessible precursors is challenging. Here we develop a nickel-catalyzed hydroalkylation method to assemble a wide range of chiral alkyl amines from enecarbamates (N-Cbz-protected enamines) and alkyl halides with high regio- and enantioselectivity. The method works for both nonactivated and activated alkyl halides and is able to produce enantiomerically enriched amines with two minimally differentiated α-alkyl substituents. The mild conditions lead to high functional group tolerance, which is demonstrated in the postproduct functionalization of many natural products and drug molecules, as well as the synthesis of chiral building blocks and key intermediates to bioactive compounds.

Photoinduced Kochi Decarboxylative Elimination for the Synthesis of Enamides and Enecarbamates from N-Acyl Amino Acids

Decarboxylative elimination of easily accessible N-acyl amino acids to provide enamide and enecarbamate building blocks has been realized through the combination of an organophotoredox catalyst and copper acetate as the terminal oxidant. This operationally simple process utilizes inexpensive and readily available reagents without preactivation of the carboxylic acid. Enamides and enecarbamates are now accessible directly from N-acyl amino acids consequently improving upon the utility of Kochi's oxidative decarboxylation of carboxylic acids.

Structure-Dependent Nickel-Catalysed Transposition of N -Allylamides to E- or Z-Enamides

The nickel-catalysed transposition of a carbon-carbon double bond of N-allyl and N-homoallyl amides is described. While the transposition of acyclic amides gave very high Z-selectivity of the enamides, corresponding cyclic N-allyl amides led exclusively t

Nickel-Catalyzed Synthesis of Enamides and Enecarbamates via Isomerization of Allylamides and Allylcarbamates

A single-component, air-stable nickel precatalyst can catalyze the isomerization of allylamides for the synthesis of enamides. The scope of the reaction encompasses various substituted allylamides and allylcarbamates as well as homoallylamides. The reaction can be performed on a multigram-scale without specialized glove-box equipment or Schlenk techniques.

Photoredox-induced three-component Oxy-, Amino-, and Carbotrifluoromethylation of enecarbamates

A photoredox-catalzyed trifluoromethylation of enecarbamates process is reported. This pathway uses Togni's reagent as the CF3 source and follows a radical/cationic pathway. Under the optimized conditions using [Ru(bpy)3(PF6)2] as the photocatalyst, a wide range of substituted enecarbamates can readily be difunctionalized by means of various O, N, and C nucleophiles.

Axially chiral dicarboxylic acid catalyzed activation of quinone imine ketals: Enantioselective arylation of enecarbamates

The synthetic utility of quinone imine ketals in the context of asymmetric catalysis was disclosed for the first time. By expanding the utility of chiral Bronsted acid catalysis to the electrophilic activation of quinone imine ketals, we succeeded in the development of highly enantioselective arylation of encarbamates to give α-amino-β-aryl ethers wherein quinone imine ketals act as functionalized aromatic ring surrogate. Further transformations of the products were also examined to establish procedures to provide chiral β-aryl amines and α-aryl esters.

A stereoselective synthesis of primary (Z)-enecarbamates from α- amidoalkylphenyl sulfones

A base assisted elimination of phenylsulfinic acid from α- amidoalkylphenyl sulfones leads to the synthesis of the corresponding enecarbamates. The Z stereoisomer of the enecarbamate is preferentially formed.