4336-19-0

Usage

Synthesis Reference(s)

Synthetic Communications, 14, p. 1193, 1984 DOI: 10.1080/00397918408076799

InChI:InChI=1/C10H14O4/c1-13-9(11)7-5-3-4-6-8(7)10(12)14-2/h3-6H2,1-2H3

Upstream product

• 67-56-1 methanol 
• 2426-02-0 3,4,5,6-Tetrahydrophthalic anhydride 
• 186581-53-3 diazomethane 
• 140459-96-7 (1R,2R)-1,2-cyclohexanedicarboxylic acid dimethyl ester 
• 46022-05-3 (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid 
• 1292320-69-4 (1R,2R)-2-(nitromethyl)cyclohexane-1-carboxylic acid 
• 505-48-6 octane-1,8-dioic acid 
• 624-49-7 dimethylfumarate 
• 84565-17-3 C₁₁H₁₂O₄^(2-)*2Li⁽¹⁺⁾ 
• 3014-58-2 dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 
• 74-88-4 methyl iodide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 14309-54-7 dimethyl cyclohexa-1,4-diene-1,2-dicarboxylate 
• 4336-20-3 dimethyl 1,2-cyclohexanedicarboxylate 

Downstream Products

• 149141-02-6 3-bromo-1-cyclohexene-1,2-dicarboxylic acid dimethylester 
• 3999-69-7 1,2-bis-1-cyclohexene 
• 75676-78-7 1,2-bis-1-cyclohexene diformate 

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.

Synthetic studies on CP-225,917 and CP-263,114: Access to advanced tetracyclic systems by intramolecular conjugate displacement and [2,3]-wittig rearrangement

An advanced intermediate related to the structures of CP-225,917 and CP-263,114 was constructed by a sequence based on the use of Grob-like fragmentation, intramolecular conjugate displacement, and [2,3]-Wittig rearrangement. A variant of the [2,3]-Wittig rearrangement was developed.

The first, general, highly efficient method for preparing tetrasubstituted epoxides using HOF·CH3CN

Tetrasubstituted epoxides, and especially electron-depleted ones, generally are difficult to prepare. HOF·CH3CN complex, probably the best oxygen transfer agent known today, epoxidizes tetrasubstituted alkenes at 0 °C in a matter of minutes or less in excellent yields. HOF·CH3CN complex is very easy to prepare by bubbling diluted fluorine (commercial) through aqueous acetonitrile. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Bis-esters from maleic anhydrides under neutral conditions: Protection of the anhydride of the natural product cornexistin

Trimethylsilyldiazomethane converts maleic anhydride derivatives in alcoholic THF to bis-esters. The highly acid and base sensitive natural product cornexistin was converted to its bis-methyl ester in 70-75% yield and to the mixed benzyl/methyl ester in 61% yield. The mixed ester can be converted back to cornexistin via transfer hydrogenation.

Alicyclic diamine fungicides

Use of a compound having the general formula: STR1 wherein R1, R2, R3 and R4 which may be the same or different represent hydrogen atoms or alkyl groups of 1-6 carbon atoms, or NR1 R2 and/o

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.

DIALKYL-SUBSTITUTED MALEATES FROM α-BROMOESTERS

Dialkyl-substituted maleates were prepared by the dimerization of α-bromoesters by treating with LDA and CuI.

STEREOSELECTIVE ALKYLATION OF THE LITHIUM DI-ENOLATE OF BIS-2,3-CARBOMETHOXY BICYCLOHEPT-5-ENE. A CONVENIENT SYNTHESIS OF MONO- AND DISUBSTITUTED FUMARATE ESTERS.

The diesters formed by a Diels-Alder reaction between cyclopentadiene and methyle maleate or fumarate give the same lithium dienolate which is stereoselectively mono- or dialkylated.The products obtained are good precursors for substituted fumarate esters.