33698-85-0

Usage

Uses

Used in Pharmaceutical Industry:
(E)-1-Chloro-2-pentene-1-one is used as a synthetic intermediate for the production of (1S,2R)-Tapentadol Hydrochloride (T007225), which is the (1S,2R)-isomer of Tapentadol (T007200, HCl). Tapentadol is a novel, centrally acting oral analgesic with a dual mode of action that has demonstrated efficacy in preclinical and clinical models of pain relief. (E)-1-Chloro-2-pentene-1-one serves as a crucial component in the development of new and effective pain management medications.

Upstream product

• 13991-37-2 trans-2-pentenoic acid 

Downstream Products

• 131140-04-0 (1R,2R)-2-hydroxycyclohexyl (E)-2-pentenoate 
• 161392-20-7 (E)-Pent-2-enethioic acid S-{(R)-1-hexyloxymethyl-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl} ester 
• 188559-05-9 (R)-N-[(E)-EtCHCHC(O)]-4-phenyl-1,3-oxazolidin-2-one 
• 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 
• 29428-84-0 trans-artemidin 
• 657395-58-9 1-benzyl-2-[(E)-2-pentenoyl]-5,5-dimethyl-pyrazolidin-3-one 
• 939125-14-1 (E)-N-[2-amino-6-(benzyloxy)-5-nitrosopyrimidin-4-yl]pent-2-enamide 
• 174590-38-6 (4R)3-(1-oxo-2-pentenyl)-4-phenyl-2-oxazolidinone 
• 39567-23-2 7-ethyl-5-oxo-2,3,6,7-tetrahydro-5H-thiazolo[3,2-a]pyrimidine 
• 1039361-95-9 N-benzyl-N-(3-oxobutyl)-(E)-3-pent-2-enamide 
• 678991-38-3 (-)-(1'S,2'S,3R)-3-dibenzylamino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)pentanamide 
• 137428-40-1 (R)-3-N,N-dibenzylaminopentanoic acid methyl ester 
• 869468-26-8 (+)-(1'S,2'S,3R)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)pentanamide 

Relevant academic research and scientific papers

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.

Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-: A] indoles via intermolecular [3+2] cycloaddition

The intermolecular diastereoselective and enantioselective synthesis of pyrrolo[1,2-a]indoles is developed through a [3+2] cycloaddition between silyl-indole derivatives and α,β-unsaturated N-acyl oxazolidinones by merging photocatalysis and Lewis acid catalysis.

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.

Design, synthesis, antiproliferative activity and docking studies of quinazoline derivatives bearing 2,3-dihydro-indole or 1,2,3,4-tetrahydroquinoline as potential EGFR inhibitors

Eight series of quinazoline derivatives bearing 2,3-dihydro-indole or 1,2,3,4-tetrahydroquinoline were designed, synthesized and evaluated for the IC50 values against three cancer cell lines (A549, MCF-7 and PC-3). Most of the forty nine target compounds showed excellent antiproliferative activity against one or several cancer cell lines. The compound 13a showed the best activity against A549, MCF-7 and PC-3 cancer cell lines, with the IC50 values of 1.09 ± 0.04 μM, 1.34 ± 0.13 μM and 1.23 ± 0.09 μM, respectively. Eight selected compounds were further selected to evaluated for the inhibitory activity against EGFR kinase. Three of them showed equal activity against EGFR kinase to positive control afatinib. AnnexinV-FITC, propidium iodide (PI) double staining and acridine orange single staining results indicated that the compound 13a could induce apoptosis of human lung cancer A549 cells.

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.

Diastereoselective cobalt-catalyzed alkylative aldol cyclizations using trialkylaluminum reagents

(Chemical Equation Presented) Co(acac)2?·2H2O serves as an effective precatalyst for alkylative aldol cyclizations of ?±,?2-unsaturated amides with ketones using trialkylaluminum reagents. These reactions provide ?2-hydroxylactams containing three contiguous stereocenters with high levels of diastereoselection. ? 2008 American Chemical Society.

A new synthesis of pteridines substituted with branched and linear alkenyl groups at C(6). The nitroso-ene reaction of 4-(alkenoylamino)-5- nitrosopyrimidines

Pteridines substituted with a 1,1-, 1,2-, or 1,1,3-substituted alkenyl group (mostly (is)-configured) at C(6) were synthesized in high yields by the intramolecular nitroso-ene reaction of 4-(alkenoylamino)-2-amino-6-benzyloxy-5- nitroso- and 4-(alkenoylamino)-2,6-diamino-5-nitrosopyrimidines. Thus, the N-alkenoyl nitrosopyrimidines 4 and 5 provided the pteridines 6 and 7, respectively, characterized by a 1,2-disubstituted (E)-alkenyl substituent, the C(4)-(E)-geranoyl amide 13 led regio- and stereoselectively to the (E)-1,1,2-trisubstituted alkenyl-pteridine 16, and the C(4)-(Z) isomer 14 led to 17 possessing a 1,1-disubstituted alkenyl group. The trifluoromethylated butenoyl amide 15 possessing a less highly nucleophilic alkenoyl group reacted more slowly to give the trifluoromethylated vinylpteridine 18. Also the 4-(alkenoylamino)-2,6-diamino-5-nitrosopyrimidine 20 reacted more slowly than 4 and 5, and provided the pteridines 23; introduction of additional N-acyl groups as in 21 and 22 led to a considerably faster ene reaction. The X-ray crystal structure analysis of the nitroso amide 15 shows eight symmetrically independent molecules in the unit cell. In the crystalline state, the N,N- dimethylformamidine derivative 9 of 6 forms a centrosymmetric dimer with the 7,8-lactam group connected by intermolecular hydrogen bonds.

Enantioselective 1,3-dipolar cycloadditions of diazoacetates with electron-deficient olefins

Equation presented A general strategy for highly enantioselective 1,3-dipolar cycloaddition of diazoesters to β-substituted, α-substituted, and α,β-disubstituted α,β-unsaturated pyrazolidinone imides is described. Cycloadditions utilizing less reactive α,β-disubstituted dipolarophiles require elevated reaction temperatures, but still provide the corresponding pyrazolines with excellent enantioselectivities. Finally, an efficient synthesis of (-)-manzacidin A employing this cycloaddition methodology as a key step is illustrated.

Organocatalysis in conjugate amine additions. Synthesis of β-amino acid derivatives

Conjugate addition of O-protected hydroxylamines to pyrazole-derived enoates proceeds with high efficiency and enantioselectivity when chiral thioureas are used as activators. A wide variety of substrates undergo conjugate amine addition providing access to enantioenriched β-amino acid derivatives. Structural requirements for the optimal thiourea catalyst have been established, and the results suggest that it operates as a bifunctional catalyst. Copyright

An entry to a chiral dihydropyrazole scaffold: Enantioselective [3 + 2] cycloaddition of nitrile imines

We have developed a versatile strategy to access dihydropyrazoles in highly enantioenriched form. Dipolar cycloaddition of electron-deficient acceptors and in situ-generated nitrile imines proceeds with high regio- and enantioselectivity using 10 mol % chiral Lewis acid catalyst. A variety of dihydropyrazoles that incorporate functionality for further manipulation have been prepared. Copyright