150013-91-5

Upstream product

• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 105-58-8 Diethyl carbonate 
• 623-49-4 ethyl cyanoformate 

Downstream Products

• 150013-92-6 tetrahydro-3-(2-oxo-2-phenylethyl)-2H-pyran-2-one 
• 1190898-39-5 ethyl-3-((E)-4-(4-bromophenyl)but-3-enyl)-2-oxotetrahydro-2H-pyran-3-carboxylate 
• 1190898-37-3 ethyl 3-(4,4-diphenylbut-3-enyl)-2-oxotetrahydro-2H-pyran-3-carboxylate 
• 1190898-36-2 2-oxo-3-((E)-4-phenyl-but-3-enyl)-tetrahydro-pyran-3-carboxylic acid ethyl ester 
• 1190898-38-4 ethyl-3-((E)-4-(4-methoxyphenyl)but-3-enyl)-2-oxotetrahydro-2H-pyran-3-carboxylate 

Relevant academic research and scientific papers

METHODS FOR ENANTIOSELECTIVE ALLYLIC ALKYLATION OF ESTERS, LACTONES, AND LACTAMS WITH UNACTIVATED ALLYLIC ALCOHOLS

The present disclosure provides methods for enantioselective synthesis of cyclic and acyclic α-quaternary carboxylic acid derivatives via nickel-catalyzed allylic alkylation.

Substrate-directable electron transfer reactions. Dramatic rate enhancement in the chemoselective reduction of cyclic esters using SmI2-H 2O: Mechanism, scope, and synthetic utility

Substrate-directable reactions play a pivotal role in organic synthesis, but are uncommon in reactions proceeding via radical mechanisms. Herein, we provide experimental evidence showing dramatic rate acceleration in the Sm(II)-mediated reduction of cyclic esters that is enabled by transient chelation between a directing group and the lanthanide center. This process allows unprecedented chemoselectivity in the reduction of cyclic esters using SmI2-H2O and for the first time proceeds with a broad substrate scope. Initial studies on the origin of selectivity and synthetic application to form carbon-carbon bonds are also disclosed.

Studies on the mechanism, selectivity, and synthetic utility of lactone reduction using SmI2 and H2O

Although simple aliphatic esters and lactones have long been thought to lie outside the reducing range of SmI2, activation of the lanthanide reagent by H2O allows some of these substrates to be manipulated in an unprecedented fashion. For example, the SmI2-H2O reducing system shows complete selectivity for the reduction of 6-membered lactones over other classes of lactones and esters. The kinetics of reduction has been studied using stopped-flow spectrophotometry. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron-transfer to the lactone carbonyl. The radical intermediates formed during lactone reduction with SmI2-H2O can be exploited in cyclizations to give cyclic ketone (or ketal) products with high diastereoselectivity. The cyclizations constitute the first examples of ester-alkene radical cyclizations in which the ester carbonyl acts as an acyl radical equivalent.

The Discovery and Structure-Activity Relationships of 1,2,3,6-Tetrahydro-4-phenyl-1-pyridines. Dopamine Autoreceptor Agonists and Potential Antipsychotic Agents

A novel dopamine (DA) autoreceptor agonist, 1,2,3,6-tetrahydro-4-phenyl-1-pyridine (14), was identified.The structure-activity relationships surrounding this compound were studied by synthesis of analogues and evaluatio

1,3-SUBSTITUTED CYCLOALKENES AND CYCLOALKANES AS CENTRAL NERVOUS SYSTEM AGENTS

1,3-Substituted cycloalkenes and cycloalkanes are described, as well as methods for the preparation and pharmaceutical composition of same, which are useful as central nervous system agents and are particularly useful as dopaminergic, antipsychotic, and a

Photoinduced Molecular Transformations. Part 144. One-Carbon Intercalation of γ- and δ-Lactones involving the β-Scission of Alkoxyl Radicals as the Key Step: Synthesis of δ- and ε-Lactones with α-Substituents

A new general method of a one-carbon intercalation of γ-lactones to δ-lactones and δ-lactones to ε-lactones in three steps involving a selective β-scission of the alkoxyl racicals as the key step is described.The reactions of γ- and δ-lactones with lithioalkyl acetate gave an equilibrium mixture of alkyl (2-hydroxytetrahydrofuran-2-yl)acetates and alkyl (2-hydroxytetrahydropyran-2-yl)acetates, as well as their ring-opened isomers in 62-95percent yields, respectively.The photolysis of the hypoiodites of these lactols in benzene containing mercury(II) oxide and iodine with Pyrex-filtered light resulted in a selective endocyclic β-scission of the corresponding alkoxyl radicals to give alkyl iodoalkyl propanedioates in 33-70percent yields.Treatment of the iodoalkyl propanedioates with tetraethylammonium bromide and sodium hydride gave alkyl 3,4,5,6-tetrahydro-2-oxo-2H-pyran-3-carboxylates or alkyl 2,3,4,5,5a,6,7,8,9,9a-decahydro-2-oxobenzoxepine-3-carboxylate in 61-81percent yields.On the other hand, succesive treatment of ω-iodoalkyl propanedioates with tetraethylammonium bromide-sodium hydride and then benzyl bromide gave a α-disubstituted δ-lactone, which gave a α-monosubstituted δ-lactone upon heating in trifluoroacetic acid under reflux.Cyclopentanone can similarly be transformed into 2-substituted cyclohexanone via a three-step procedure.