73220-24-3

Upstream product

• 20443-88-3 2-(4-methoxyphenoxy)tetrahydro-2H-pyran 
• 68-12-2 N,N-dimethyl-formamide 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 62536-85-0 2-acetoxy-5-methoxybenzaldehyde 
• 16139-79-0 ethyl diphenylphosphonoacetate 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 150-76-5 4-methoxy-phenol 
• 140-88-5 ethyl acrylate 
• 105-36-2 ethyl bromoacetate 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 

Downstream Products

• 949448-97-9 C₁₆H₁₆O₅ 
• 20921-09-9 ethyl 3-(2-hydroxy-5-methoxyphenyl)propionate 
• 40547-03-3 6-Methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 1359857-09-2 C₁₃H₁₄O₅ 
• 1359857-29-6 C₁₉H₂₅BO₆ 
• 1359857-18-3 C₁₄H₁₃F₃O₇S 

Relevant academic research and scientific papers

Free radical scavenging and α-glucosidase inhibitory activity of (E)-methyl/ethyl-3-(2-hydroxyphenyl)acrylates

(E)-Methyl/ethyl-3-(2-hydroxyphenyl)acrylates 3a-x have been prepared by the reaction of salicylaldehydes 1a-l with Wittig reagents such as methyl (triphenylphosphoranylidene)acetate 2a and ethyl (triphenylphosphoranylidene)acetate 2b in dry DCM at room t

Cascade Synthesis of 4-Arylcoumarins: Pd-Catalyzed Arylations and Cyclizations with (E)-Ethyl 3-(2-Hydroxyaryl)acrylates and Triarylantimony Difluorides

Herein, we describe a simple general method for the synthesis of 4-arylcoumarins using pentavalent organoantimony compounds. The reactions of 3-(2-hydroxyaryl)acrylates with triarylantimony difluorides in the presence of Pd(OAc)2 (10 mol-%) and 2,2'-bipyridyl (10 mol-%) at 80 °C under aerobic conditions afforded 4-arylcoumarins in good-to-excellent yields. This protocol involves a cascade oxidative Heck-type arylation followed by cyclization, with all the aryl groups in the triarylantimony difluoride transferred to the coupling products. Triarylantimony difluorides resulted in better outcomes than those obtained with other pentavalent organoantimony or bismuth compounds.

Phenol compound ortho-position direct olefination method and olefinated phenol compound

The invention relates to a phenol compound ortho-position direct olefination method and an olefinated phenol compound prepared with the method. The method comprises the steps that a phenol compound shown by the formula (II) and an olefin compound shown by

Late-Stage Direct o-Alkenylation of Phenols by PdII-Catalyzed C?H Functionalization

o-Alkenylation of unprotected phenols has been developed by direct C?H functionalization catalyzed by PdII. This work features phenol group as a directing group and realizes highly site-selective C?H bond functionalization of phenols to achieve the corresponding products in moderate to excellent yields at 60 °C. The advantages of this reaction include unprecedented C?H functionalization using phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C?H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under this catalytic system in good yields. Furthermore, this novel method enables a late-stage modification of complex phenol-containing bioactive molecules toward a diversity-oriented drug discovery.

Benzoxaborole antimalarial agents. Part 2: Discovery of fluoro-substituted 7-(2-carboxyethyl)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles

A series of new boron-containing benzoxaborole compounds was designed and synthesized for a continuing structure-activity relationship (SAR) investigation to assess the antimalarial activity changes derived from side-chain structural variation, substituent modification on the benzene ring and removal of boron from five-membered oxaborole ring. This SAR study demonstrated that boron is required for the antimalarial activity, and discovered that three fluoro-substituted 7-(2-carboxyethyl)-1,3-dihydro-1-hydroxy-2,1-benzoxaboroles (9, 14 and 20) have excellent potencies (IC50 0.026-0.209 μM) against Plasmodium falciparum.

Enantioselective synthesis of functionalized 1-benzoxepines by phenoxide ion mediated 7-endo-tet carbocyclization of cyclic sulfates

A new asymmetric synthesis of 2,3-disubstituted 1-benzoxepines is described. Key steps include Sharpless asymmetric dihydroxylation of trans-α,β-unsaturated esters and phenoxide ion mediated intramolecular 7-endo-tet carbocyclization of syn-2,3-dihydroxy ester derived cyclic sulfates. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Phosphine-catalyzed synthesis of highly functionalized coumarins

2-Styrenyl allenoates are converted into cyclopentene-fused dihydrocoumarins through phosphine-catalyzed regio- and diastereoselective [3 + 2] cycloadditions. Remarkably, changing the solvent from THF to benzene promotes the conversion of the 2-(2-nitrostyrenyl) allenoate into a tricyclic nitronate through a previously undocumented mode of phosphine catalysis. This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives.

Convenient synthesis of a simple coumarin from salicylaldehyde and wittig reagent. IV: Improved synthetic method of substituted coumarins

The reaction of salicylaldehydes (2) with Horner-Wadsworth-Emmons (HWE) or Ando-HWE reagents was attempted to afford intramolecular phosphonate derivatives (6). A new synthetic method for coumarins (1) was achieved by using protected 2.