72448-93-2

Usage

Uses

Used in Pharmaceutical Industry:
7-Chloro-trans-2-hepenoic acid ethyl ester is used as a building block in the synthesis of various pharmaceuticals. Its unique properties make it a versatile and valuable component in the development of new drugs.
Used in Agrochemical Industry:
This chemical compound is also used in the synthesis of agrochemicals, contributing to the development of effective and innovative products for agriculture.
Used in Flavors and Fragrances Industry:
7-Chloro-trans-2-hepenoic acid ethyl ester is utilized in the production of flavors and fragrances, adding to the variety and complexity of scents and tastes in various consumer products.
Used in Organic Synthesis and Chemical Research:
As a key intermediate in organic synthesis, 7-chloro-trans-2-hepenoic acid ethyl ester is employed in chemical research to explore new reactions and develop novel compounds with potential applications in various industries.

InChI:InChI=1/C9H15ClO2/c1-2-12-9(11)7-5-3-4-6-8-10/h5,7H,2-4,6,8H2,1H3/b7-5+

Upstream product

• 5259-98-3 5-chloropentan-1-ol 
• 20074-80-0 5-chloro-pentanal 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 6139-84-0 4-chlorobutyraldehyde 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 

Downstream Products

• 489-54-3 (1R,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.0^2,7.0^10,15]heptadecane-8,16-dione 

Relevant academic research and scientific papers

Stereocontrolled synthesis and alkylation of cyclic β-amino esters: Asymmetric synthesis of a (-)-sparteine surrogate

A convenient method for the stereoselective synthesis of cyclic β-amino esters from an iodo αβ-unsaturated ester and α-methylbenzylamine is described. Subsequent enolate generation and alkylation proceeds with complete stereocontrol, with the two stereogenic centres working together. In this way, a functionalised piperidine suitable for alkaloid natural product synthesis was prepared. The usefulness of the methodology is exemplified with the concise synthesis of a (-)-sparteine surrogate. The Royal Society of Chemistry.

Umpolung of Michael acceptors catalyzed by N-heterocyclic carbenes

N-Heterocyclic carbenes can catalyze β-alkylations of a range of α,β-unsaturated esters, amides, and nitriles that bear pendant leaving groups to form a variety of ring sizes. In this process, the nucleophilic catalyst transiently transforms the normally electrophilic β carbon into a nucleophilic site through an unanticipated addition-tautomerization sequence. Copyright

Concise asymmetric synthesis of (-)-sparteine

A six-step asymmetric synthesis of natural (-)-sparteine from ethyl 7-iodohept-2-enoate is reported, involving a connective Michael addition of an amino ester-derived enolate to an α,β-unsaturated amino ester.

Asymmetric synthesis of cyclic β-amino acids

A convenient synthesis of cyclic β-amino acid derivatives (5-, 6- and 7-rings) is achieved via a four step sequence: (i) stereoselective Michael addition of substituted α-methylbenzylamines to α,β-unsaturated chloroesters; (ii) CAN-mediated deprotection; (iii) cyclisation and (iv) α-chloroethyl chloroformate-mediated α-methylbenzylamine deprotection.

N-(4-methylbenzenesulfonyl)- pyrrolidines and piperidines by a tandem S(N)2-Michael addition reaction

A tandem S(N)2-Michael addition sequence has been developed for the preparation of N-(4-methylbenzenesulfonyl)- pyrrolidines and piperidines bearing functionalized side chains at C-2.

Lithium-Halogen Exchange-Initiated Cyclization Reactions. 3. Intramolecular Conjugate Addition Reactions of Unsaturated Acylphosphoranes

The lithium-halogen exchange-initiated intramolecular conjugate addition reactions of some model unsaturated acylphosphoranes have been examined.The effects of halide type, chain length, and acceptor substitution pattern on the feasibility of ring construction were studied.The lithium-bromine exchange reactions in two 2-bromooaryl acceptors were found to be too slow, relative to competing side reactions, to allow practical carbocycle syntheses while 3-,4-,5-, and 6-membered carbocycles are formed in good to excellent yields from precursors that are vinyl and saturated primary iodides.Highly efficient intramolecular conjugate addition reactions to β,β-disubstituted acceptor units are possible, and intermediate anions from intramolecular conjugate addition reactions are readily captured with electrophiles.