33698-85-0

Basic information

• Product Name: (E)-1-Chloro-2-pentene-1-one
• Synonyms: (E)-1-Chloro-2-pentene-1-one;(E)-2-Pentenoyl chloride;(2E)-Pent-2-enoyl chloride
• CAS NO: 33698-85-0
• Molecular Formula: C₅H₇ClO
• Molecular Weight: 118.56
• Mol File: 33698-85-0.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-1-Chloro-2-pentene-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-Chloro-2-pentene-1-one(33698-85-0)
• EPA Substance Registry System: (E)-1-Chloro-2-pentene-1-one(33698-85-0)

Safety Data

• Hazardous Substances Data: 33698-85-0(Hazardous Substances Data)

Usage

Uses

trans-2-Pentenoic Acid Chloride is an intermediate useful in the synthesis of (1S,2R)-Tapentadol Hydrochloride (T007225), which is the (1S,2R)-isomer of Tapentadol (T007200, HCl); a novel, centrally acting oral analgesic with a dual mode of action that has demonstrated efficacy in preclinical and clinical models of pain relief.

Upstream product

• 13991-37-2 trans-2-pentenoic acid 

Downstream Products

• 139962-51-9 (4R,5S)-1,5-Dimethyl-3-((E)-pent-2-enoyl)-4-phenyl-imidazolidin-2-one 
• 133729-84-7 (4S,3'S)-3-(3'-methyl-1'-oxopentyl)-4-benzyl-2-oxazolidinone 
• 188559-05-9 (R)-N-[(E)-EtCHCHC(O)]-4-phenyl-1,3-oxazolidin-2-one 
• 682812-15-3 tert-butyl (E)-pent-2-enoylcarbamate 
• 939125-14-1 (E)-N-[2-amino-6-(benzyloxy)-5-nitrosopyrimidin-4-yl]pent-2-enamide 
• 176792-02-2 (4S,5R)-1-((2R,3S)-3-Ethyl-aziridine-2-carbonyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 
• 174485-45-1 (4S)-3-((2E)-pent-2-enoyl)-4-phenyl oxazolidin-2-one 
• 678991-33-8 E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)pent-2-enamide 
• 657395-58-9 1-benzyl-2-[(E)-2-pentenoyl]-5,5-dimethyl-pyrazolidin-3-one 
• 29428-84-0 trans-artemidin 
• 304467-43-4 (1S,5R,7R)-10,10-Dimethyl-4-((E)-pent-2-enoyl)-3-phenyl-3,4-diaza-tricyclo[5.2.1.0^1,5]decan-2-one 
• 247233-89-2 (S_S)-N-[(E)-Pent-2-enoyl]-2-(p-tolylsulfinyl)pyrrole 
• 161392-20-7 (E)-Pent-2-enethioic acid S-{(R)-1-hexyloxymethyl-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl} ester 
• 131140-04-0 (1R,2R)-2-hydroxycyclohexyl (E)-2-pentenoate 

Relevant articles and documents

On the role of the vinylsulfoxide side chain of dirchromone towards its bioactivities

Analogs of dirchromone were prepared to shed light on the pivotal role of its peculiar vinylsulfoxide side chain towards its cytotoxic and antimicrobial properties, especially dependant upon the presence and oxidation state of sulfur. The reaction of dirchromone with cysteamine revealed a surprising Michael acceptor behavior with elimination of the methylsulfinyl moiety and redox transformation of the sulfur atom that could be involved in the mode of action of dirchromone within cells.

Nucleophilic halo-michael addition under lewis-base activation

A simple and general conjugate nucleophilic halogenation is presented. The THTO/halosilane combination has shown the ability to act as a nucleophilic halide source in the conjugate addition to a variety of Michael acceptors. In addition, a straightforward diastereoselective halogen installation using α,β-unsaturated acyloxazolidinones as platforms has been developed.

Organocatalytic access to enantioenriched dihydropyran phosphonates via an inverse-electron-demand hetero-Diels-Alder reaction

The enantioselective inverse-electron-demand hetero-Diels-Alder reaction of the remote olefin functionality in dienamines has been developed by the simultaneous activation of α,β-unsaturated aldehydes and acyl phosphonates. The dual activation is based on an organocatalyst that activates both the α,β-unsaturated aldehyde, through dienamine formation, and the acyl phosphonate by hydrogen-bonding. The enantioselective reaction results in the formation of dihydropyran frameworks with three contiguous stereogenic centers. Different substitution patterns are possible for both the heterodiene and the dienophile, and the target products are obtained in good yields and up to 92% ee. The potential of the reaction is demonstrated by transformation of the products into valuable and complex synthons.