86109-34-4

Upstream product

• 115240-92-1 methyl 2-[hydroxy(4-methoxyphenyl)methyl]prop-2-enoate 
• 554-12-1 propanoic acid methyl ester 
• 121-98-2 methyl 4-methoxybenzoate 
• 616-38-6 carbonic acid dimethyl ester 
• 121-97-1 4-Methoxypropiophenone 
• 614-45-9 tert-Butyl peroxybenzoate 
• 22027-50-5 methyl 3-(4-methoxybenzoyl)acetate 
• 615-43-0 2-iodophenylamine 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 74-88-4 methyl iodide 
• 123-11-5 4-methoxy-benzaldehyde 
• 105-37-3 Ethyl propionate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 17226-85-6 α,β-syn-methyl 3-hydroxy-2-methyl-3-(p-methoxyphenyl)propionate 
• 17226-85-6 α,β-anti-methyl 3-hydroxy-2-methyl-3-(p-methoxyphenyl)propionate 
• 343305-15-7 5-(4-methoxyphenyl)-4-methyl-3-isoxazolol 
• 136734-11-7 (2R,3R)-methyl 3-hydroxy-3-(4′-methoxyphenyl)-2-methylpropanoate 
• 85199-56-0 (2S,3S)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester 
• 159108-90-4 (+)-(2,3-syn)-3-(4-methoxyphenyl)-2-methylpropane-1,3-diol 
• 159108-93-7 (+)-(2,3-syn)-3-methoxy-3-(4-methoxyphenyl)-2-methylpropan-1-ol 
• 159108-94-8 (+)-(3,4-syn)-4-methoxy-4-(4-methoxyphenyl)-3-methylbutanenitrile 
• 159108-91-5 (+)-(1,2-syn)-3-(tert-butyldimethylsiloxy)-1-(4-methoxyphenyl)-2-methylpropan-1-ol 
• 159108-92-6 (+)-(1,2-syn)-3-(tert-butyldimethylsiloxy)-1-methoxy-1-(4-methoxyphenyl)-2-methylpropane 
• 119068-85-8 (2S,3S)-methyl 3-hydroxy-3-(4′-methoxyphenyl)-2-methylpropanoate 
• 119018-10-9 (2R,3R)-methyl 3-acetoxy-3-(4-methoxyphenyl)-2-methylpropanoate 
• 159171-19-4 (2S,3S)-methyl 3-acetoxy-3-(4-methoxyphenyl)-2-methylpropanoate 
• 119018-11-0 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,2S)-2-methoxycarbonyl-1-(4-methoxy-phenyl)-propyl ester 

Relevant academic research and scientific papers

Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3-Oxazin-6-One Derivatives

A palladium catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed. In the reaction, a cascade process involving ring-opening/cyclization was suggested. The reaction features high atomic economy due to no elimination of CO2 occurred. Moreover, products obtained demonstrate aggregation-induced emission properties with relatively high solid-state emission efficiencies. (Figure presented.).

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds

Iron-catalysed 1,2-acyl migration of tertiary α-azido ketones and 2-azido-1,3-dicarbonyl compounds provides a simple and atom-economical approach toward enamides and isoquinolones. This paper reports two catalyst systems for these transformations which employ iron(ii) complexes [Fe(dpbz)]Br2 (dpbz = 1,2-bis(diphenylphosphino)benzene) and FeBr2/Et3N, respectively. [Fe(dpbz)]Br2 was found to be highly effective at converting 2-azido-2,3-dihydro-1H-inden-1-ones to isoquinolones. The reagent combination of FeBr2/Et3N, on the other hand, exhibited a broader catalytic scope, owing to the beneficial effect of Et3N. This latter catalyst system enables 2-azido-2-methyl-1,3-dicarbonyl compounds to be converted to the corresponding enamides under mild conditions in good yields.

Controlled and efficient synthesis of quinoline derivatives from Morita-Baylis-HILLMAN adducts by palladium-catalyzed heck reaction and cyclization

An efficient synthesis of 2,3-disubstituted quinoline derivatives from easily accessible (het)aryl-substituted Morita-Baylis-Hillman (MBH) adducts was achieved by an approach involving a palladium-catalyzed Heck reaction and cyclization. This strategy converts the MBH adducts into α-benzyl β-keto ester derivatives that can cyclize into the corresponding quinolines in good yields.

Morita-Baylis-Hillman adducts as building blocks of heterocycles: a simple approach to 4-substituted pyrazolones, and mechanism investigation via ESI-MS(/MS)

Abstract We describe herein an efficient approach for the preparation of 4-substituted 2,3-dihydro-1H-pyrazol-3-ones starting from Morita-Baylis-Hillman adducts. These heterocycles were obtained in two or three steps as single isomers with moderate to goo

Tert -butyl peroxybenzoate-promoted α-methylation of 1,3-dicarbonyl compounds

A tert-butyl peroxybenzoate (TBPB)-promoted direct α-methylation of 1,3-dicarbonyl compounds has been developed, providing α-methyl derivatives in moderate to good yields. In this procedure, TBPB plays a dual role, serving as both the methyl source and radical initiator. This work represents a key complement to the traditional α-methylation of 1,3-dicarbonyl compounds using methyl iodide.

Reductive Reformatsky-Honda reaction of α,β-unsaturated esters: Facile formation of 1,3-dicarbonyl compounds and β-hydroxy esters

The reaction of tris(triphenylphosphine)rhodium chloride [RhCl(PPh 3)3] with diethylzinc (Et2Zn) easily afforded a rhodium-hydride complex that effects the 1,4-reduction of α,β- unsaturated esters to give rhodium enolates. Formation of the rhodium enolate is followed by transmetalation with the zinc species to give a Reformatsky-type reagent, and this reacts with various acid chlorides at the α-position to give β-keto esters. The Reformatsky-type reagent also reacts with various electrophiles such as aldehydes, ketones and acid anhydrides to give the corresponding products in which the electrophiles were introduced reductively at the α-position of α,β-unsaturated esters. Copyright

Substrate range of the titanium TADDOLate catalyzed asymmetric fluorination of activated carbonyl compounds

The substrate range of the [TiCl2(TADDOLate)] (TADDOL=α,α,α′,α′-tetraaryl-1,3-dioxolane-4, 5-dimethanol)-catalyzed asymmetric α-fluorination of activated β-carbonyl compounds has been investigated. Optimal conditions for catalysis are characterized by using 5 mol-% of TiCl2(naphthalen-1- yl)-TADDOLate) as catalyst in a saturated (0.14 mol/l) MeCN solution of F-TEDA (1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis- [tetrafluoroborate]) at room temperature. A series of α-methylated β-keto esters (3-oxobutanoates, 3-oxopentanoates) with bulky benzyl ester groups (60-90% ee) or phenyl ester (67-88% ee) have been fluorinated readily, whereas α-acyl lactones were also readily fluorinated, but gave lower inductions (13-46% ee). Double stereochemical differentiation in β-keto esters with chiral ester groups raised the stereoselectivity to a diastereomeric ratio (dr) of up to 96.5:3.5. For the first time, β-keto S-thioesters were asymmetrically fluorinated (62-91.5% ee) and chlorinated (83% ee). Lower inductions were observed in fluorinations of 1,3-diketones (up to 40% ee) and β-keto amides (up to 59% ee). General strategies for preparing activated β-carbonyl compounds as important model substrates for asymmetric catalytic α-functionalizations are presented (>60 examples). Copyright

Synthesis and biological activity of new (E)-α-(Methoxyimino) benzeneacetate derivatives containing a substituted pyrazole ring

Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin analogues with high activity, a series of new strobilurin derivatives containing a substituted pyrazole in the side chain were synthesized and their biological activities were tested. The compounds were identified by 1H nuclear magnetic resonance, infrared, and elemental analysis. The test results indicated that the compounds exhibited strong fungicidal activities against Pyricularia oryzae, Phytophthora infestans, Pseudoperonospora cubenssi, and Erysiphe graminis. The relationship between structure and biological activity is discussed in terms of the effects of the substituents on the pyrazole ring. The present work demonstrates that strobilurin analogues with a 3-(substituted phenyl)-1 H-pyrazol-5-oxy side chain can be used as possible lead compounds for the development of potential agrochemicals.

Structural determinants for AMPA agonist activity of aryl or heteroaryl substituted AMPA analogues. Synthesis and pharmacology

We have previously reported the synthesis and pharmacological characterization of analogues of 2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA, 1a), in which the methyl group was replaced by a phenyl group (APPA, 1b) or heteroaryl groups. While 2b and its 3-pyridyl analogue 2-amino-3-[3-hydroxy-5-(3-pyridyl)-4-isoxazolyl]propionic acid (3-Py-AMPA, 3) show very low affinity for AMPA receptors, introduction of heteroaryl substituents containing heteroatom in the 2-position provides potent AMPA receptor agonists. We here report the synthesis and pharmacology of 2-amino-3-(3-hydroxy-5-pyrazinyl-4-isoxazolyl)propionic acid (7) (IC50 = 1.2 μM; EC50 = 11 μM), which is weaker as an AMPA agonist than AMPA (IC50 = 0.040 μM; EC50 = 3.5 μM) but comparable in potency with 2-Py-AMPA (4) (IC50 = 0.57 μM; EC50 = 7.4 μM), as determined in radioligand binding and electrophysiological experiments, respectively. The AMPA analogues 8a-c, containing 2-, 3-, or 4-methoxyphenyl substituents, respectively, and the corresponding hydroxyphenyl analogues, 9a-c, were also synthesized and evaluated pharmacologically. With the exception of 2-amino-3-[3-hydroxy-5-(2-hydroxyphenyl)-4-isoxazolyl]propionic acid (9a), which is a very weak AMPA agonist (IC50 = 45 μM; EC50 = 324 μM), none of these compounds showed detectable effect at AMPA receptors.

RuCl2(PPh3)3 catalyzed isomerization of the Baylis-Hillman adducts

RuCl2(PPh3)3 catalyzed isomerization of the Baylis-Hillman adducts i.e. methyl 3-aryl-3-hydroxy-2-methylenepropanoates to methyl 3-aryl-2- methyl-3-oxopropanoates has been described.