13368-79-1

Usage

Synthesis Reference(s)

Synthetic Communications, 14, p. 227, 1984 DOI: 10.1080/00397918408060726

InChI:InChI=1/C9H12O4/c1-12-8(10)6-4-3-5-7(6)9(11)13-2/h3-5H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 3128-15-2 cyclopent-1-ene-1,2-dicarboxylic acid 
• 68252-17-5 Dimethyl cyclopentane-1,2-dicarboxylate 
• 111-16-0 heptanedioic acid 
• 106-65-0 Dimethyl succinate 
• 868-73-5 dimethyl 2,6-dibromoheptadioate 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 92224-44-7 2,3,6,7-tetrahydro-1H-cyclopenta[d]pyridazine-1,4(5H)-dione 
• 91846-80-9 1,4-dichloro-6,7-dihydro-5H-cyclopenta[d]pyridazine 
• 344747-26-8 methyl 2-(hydroxymethyl)cyclopent-1-ene-1-carboxylate 
• 14668-74-7 2-Hydroxymethyl-cyclopent-1-en-1-carbonsaeure 
• 91101-10-9 4-(2-Oxotetrahydro-3-furanyl)-imidazolidin-2,5-dion 

Relevant academic research and scientific papers

Synthetic method of alicyclic diester

The invention discloses a synthetic method of alicyclic diester. The synthetic method comprises the following steps: enabling diacid comprising a multi-carbon lipid chain end group or diester containing a multi-carbon lipid chain end group to react with a first halogenation reagent, after the reaction is completed, adding a second halogenation reagent into a reaction product, after the reaction iscompleted, re-esterifying, and obtaining the di-ester of di-halogenation; adding the di-ester of the di-halogenation into an organic solvent, adding alkali to perform the reaction, after the reactionis completed, adding acid to perform the neutralization, and obtaining annular di-ester; and performing the reduction reaction for the annular di-ester, and obtaining the alicyclic diester. By adopting the synthetic method, a novel reaction path is developed, and the direct-chain end-group diacid or diester is used as a raw material to prepare the alicyclic diester by virtue of bromination reaction, ring-closing reaction and the reduction reaction. The initial raw material is low in cost, the process is simple, the reaction condition requirement is low, the safety is good, the product yield and purity are high, and the mass production is easy to realize. Moreover, the diester of a three-membered ring to an eighteen-membered ring can be prepared by utilizing the synthetic method of the invention.

A CYCLOPENTANE, CYCLOPENTENE AND CYCLOPENTANONE ANNULATION METHODOLOGY

The chemistry derived from the dienolates of 1,2-dicarboxylic acid esters is described.New methods for preparing cyclopentane, cyclopentene and cyclopentanone rings affixed to the diesters are discussed.

Metall-assisted Cycloadditions. Part 1. Synthesis of Substituted Cyclopentane-derivatives obtained from the Reactions of (η1-Allyl)dicarbonyl(η5-cyclopentadienyl)iron with Electron-deficient Olefins and Acetylenes

(η1-Allyl)dicarbonyl(η5-cyclopentadienyl)iron has been treated with various electron-deficient cyano- and alkoxycarbonyl-substituted olefins and dimethyl acetylenedicarboxylate.The resulting cyclopentyl-Fp complexes have been subjected to demetallation reactions employing various reagents.Alkoxycarbonyl esters of the substituted cyclopentanes were isolated by oxidative carboxylation with ceric ammonium nitrate, and cyclic and linear products have been obtained with hydrogen chloride by cleavage of the Fe-C bond.N-Bromopyridinium bromide has yielded a mixture of bromocyclopentane derivatives and cyclopentenes. β-Hydride abstraction, with trityl tetrafluoroborate, of complex (12c) has resulted in the formation of diethyl but-3-enylmalonate.