637356-88-8

Basic information

• Product Name: DIETHYL 3,4,5-TRIMETHOXYPHENYL MALONATE
• Synonyms: DIETHYL 3,4,5-TRIMETHOXYPHENYL MALONATE;2-(3,4,5-Trimethoxyphenyl)-malonic acid diethylester
• CAS NO: 637356-88-8
• Molecular Formula: C₁₆H₂₂O₇
• Molecular Weight: 326.34
• Mol File: 637356-88-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DIETHYL 3,4,5-TRIMETHOXYPHENYL MALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL 3,4,5-TRIMETHOXYPHENYL MALONATE(637356-88-8)
• EPA Substance Registry System: DIETHYL 3,4,5-TRIMETHOXYPHENYL MALONATE(637356-88-8)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 637356-88-8(Hazardous Substances Data)

Upstream product

• 39053-78-6 3,4,5-trimethoxyphenylacetyl chloride 
• 951-82-6 3,4,5-trimethoxyphenyl acetic acid 
• 25245-29-8 5-iodo-1,2,3-trimethoxybenzene 
• 105-53-3 diethyl malonate 
• 623-49-4 ethyl cyanoformate 
• 66162-60-5 (3,4,5-trimethoxyphenyl)acetic acid ethyl ester 

Downstream Products

• 637356-47-9 3-azido-2-(3,4,5-trimethoxyphenyl)propan-1-ol 
• 637356-97-9 2-(3,4,5-trimethoxyphenyl)propane-1,3-diol 

Relevant articles and documents

Enzymatic desymmetrization of prochiral 2-substituted-1,3-diamines: Preparation of valuable nitrogenated compounds

A wide range of prochiral 1, 3-diamines were first efficiently synthesized and subsequently desymmetrized by using lipase from Pseudomonas cepacia as catalyst and diallyl carbonate as alkoxycarbonylating agent. In all cases, the amino carbamates of R-configuration were recovered. Final selective cleavage of the N-allyloxycarbonyl moiety was carried out under mild reaction conditions, which demonstrates the high versatility and potential of this chemoenzymatic route as a source of intermediates in the synthesis of related optically active nitrogenated derivatives.

Room-temperature copper-catalyzed α-arylation of malonates

An effective method in targeting α-aryl malonates is reported. In the presence of a catalytic amount of 2-picolinic acid and Cul, the coupling of aryl iodides with diethyl malonate proceeds smoothly even at room temperature. The high levels of functional group compatibility and exceptionally mild reaction conditions offer this an attractive protocol in accessing a variety of arylated malonates.

Unusual Tethering Effects in the Schmidt Reaction of Hydroxyalkyl Azides with Ketones: Cation-π and Steric Stabilization of a Pseudoaxial Phenyl Group

The Lewis acid-promoted reactions of chiral 2-aryl-3-azido-1-propanols with 4-substituted cyclohexanones lead to iminium ethers and ultimately caprolactams (following a hydrolysis step). In this study, it is shown that these reactions afford variable ratios of products, depending on the electronic nature of the phenyl group. These results are interpreted in the context of a cation?π stabilizing effect in the product-determining reaction intermediate. Remarkably, the best selectivity was obtained when an azidopropanol reagent containing a quaternary center was used; a control experiment showed that the high selectivity observed in this result depended upon the free rotation of the pseudoaxial aromatic group in the intermediate that affords the major product. Copyright