80887-79-2

Upstream product

• 64-17-5 ethanol 
• 405554-08-7 2-(4-benzyloxy-phenyl)-malononitrile 
• 23197-67-3 diethyl 2-(4-methoxyphenyl)malonate 
• 106-48-9 4-chloro-phenol 
• 105-53-3 diethyl malonate 
• 106-41-2 4-bromo-phenol 
• 17138-28-2 (4-hydroxy-phenyl)-acetic acid ethyl ester 
• 623-49-4 ethyl cyanoformate 
• 19578-68-8 4-(4-benzyloxyphenyl) iodide 
• 540-38-5 p-Iodophenol 

Downstream Products

• 170784-80-2 2-(4-pentyloxyphenyl)-1,3-propanediol 
• 913653-73-3 2-(4-propoxyphenyl)-1,3-propanediol 
• 116528-60-0 2-(4-hexyloxyphenyl)-1,3-propanediol 
• 75552-39-5 2-(4-butoxyphenyl)-1,3-propanediol 
• 150611-03-3 Ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzothiazolyl)-2-ethoxycarbonylpropionate 
• 167979-41-1 2-[4-(1-tert-butoxycarbonyl-pyrrolidin-3-yloxy)-phenyl]-2-(6-cyano-benzothiazol-2-ylmethyl)-malonic acid diethyl ester 
• 150610-51-8 diethyl 2-(4-{[(3S)-1-(tert-butoxycarbonyl)pyrrolidin-3-yl]oxy}phenyl)malonate 

Relevant academic research and scientific papers

Arylation of diethyl malonate and ethyl cyanoacetate catalyzed by palladium/di-tert-butylneopentylphosphine

α-Arylated carbonyl derivatives are important structural motifs in many natural products and pharmaceutically active compounds. Although arylation of simple monocarbonyl compounds is a well-established methodology, metal-catalyzed arylation of β-dicarbonyl derivatives is significantly more challenging. The ability of β-dicarbonyl anions to bind to palladium in a κ2-O,O mode, rather than the κ1-C-bound mode required for bond formation, often results in the deactivation of catalyst systems. The C-bound form of the enolate can be favored through the use of sterically demanding ligands. Herein, we report that the sterically demanding di-tert-butylneopentylphosphine (DTBNpP) ligand in combination with Pd(dba)2 provides an effective catalyst for the coupling of aryl bromides and chlorides with diethyl malonate. The Pd/DTBNpP system also catalyzes the coupling of aryl bromides with ethyl cyanoacetate.

Optimization of a 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione series of HIV capsid assembly inhibitors 2: Structure-activity relationships (SAR) of the C3-phenyl moiety

Detailed structure-activity relationships of the C3-phenyl moiety that allow for the optimization of antiviral potency of a series of 1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione inhibitors of HIV capsid (CA) assembly are described. Combination of favorable substitutions gave additive SAR and allowed for the identification of the most potent compound in the series, analog 27. Productive SAR also transferred to the benzotriazepine and spirobenzodiazepine scaffolds, providing a solution to the labile stereocenter at the C3 position. The molecular basis of how compound 27 inhibits mature CA assembly is rationalized using high-resolution structural information. Our understanding of how compound 27 may inhibit immature Gag assembly is also discussed.

Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds

The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

A general and mild copper-catalyzed arylation of diethyl malonate

Chemical equation presented A general method for the synthesis of α-aryl malonates is described. The coupling of an aryl iodide and diethyl malonate in the presence of Cs2CO3 and catalytic amounts of copper(I) iodide and 2-phenylphenol affords the α-aryl malonate in good to excellent yields. The mild reaction conditions and high levels of functional group compatibility make this an attractive synthetic alternative to previous methods.

A new series of liquid crystals having a terminal carbonyl group

Some homologs of 5-(4-alkoxyphenyl)-1,3-dioxan-2-one exhibit a monotropic smectic A phase commencing from the pentyloxy homolog.

AROMATIC AMIDINE DERIVATIVES AND SALTS THEREOF

An anticoagulant agent which comprises, as an active ingredient, an aromatic amidine derivative represented by the following general formula (1) or a salt thereof: STR1 wherein the group represented by STR2 is a group selected from indolyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, naphthyl, tetrahydronaphthyl and indanyl; X is a single bond, an oxygen atom, a sulfur atom or a carbonyl group; and Y is a saturated or unsaturated 5-or 6-membered heterocyclic moiety or cyclic hydrocarbon moiety optionally having a substituent group, an amino group optionally having a substituent group or an aminoalkyl group optionally having a substituent group.The inventive compound has a high anticoagulant capacity based on its excellent FXa inhibition activity.