165115-73-1

Usage

Uses

Used in Pharmaceutical Industry:
1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]is used as a building block for the synthesis of pharmaceuticals due to its unique chemical structure and properties. The difluorophenyl and propen-1-yl groups in 1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]- can be utilized to create new drug molecules with specific therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical industry, 1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]is employed as a building block for the synthesis of agrochemicals. Its specific chemical properties can contribute to the development of new compounds with improved efficacy in crop protection and pest control.
Used in Organic Chemistry Reactions:
1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]is used as a reagent in various organic chemistry reactions. Its unique structure allows it to participate in a range of chemical transformations, facilitating the synthesis of complex organic molecules.
Used as a Solvent in Industrial Processes:
In some industrial processes, 1,3-PROPANEDIOL, 2-[2-(2,4-DIFLUOROPHENYL)-2-PROPEN-1-YL]is employed as a solvent. Its ability to dissolve a variety of substances and its compatibility with different materials make it suitable for use in various applications, including chemical manufacturing and processing.

InChI:InChI=1/C12H14F2O2/c1-8(4-9(6-15)7-16)11-3-2-10(13)5-12(11)14/h2-3,5,9,15-16H,1,4,6-7H2

Upstream product

• 141113-36-2 2-(2,4-difluorophenyl)allyl alcohol 
• 159276-58-1 1-(1-Bromomethyl-vinyl)-2,4-difluoro-benzene 
• 372-18-9 1,3-Difluorobenzene 
• 149509-28-4 1-Chloro-2-(2,4-difluorophenyl)-3-trimethylsilyl-2-propanol 
• 156570-10-4 1-(1-chloromethylethenyl)-2,4-difluorobenzene 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 159276-62-7 diethyl 2-[2-(2,4-difluorophenyl)-2-propen-1-yl]-1,3-propanedioate 

Downstream Products

• 623573-88-6 5-[2-(2,4-difluoro-phenyl)-allyl]-2-phenyl-[1,3]dioxane 
• 192448-07-0 2-methylpropanoic acid [(2S)-4-(2,4-difluorophenyl)-2-hydroxymethyl-4-penten-1-yl] ester 
• 171228-49-2 posaconazote 
• 1350560-52-9 C₁₆H₁₉F₂IO₃ 
• 149809-43-8 (2R-cis)-2-(2,4-difluorophenyl)-4-[[(4-methylphenyl)sulfonyloxy]methyl]-2-[(1H-1,2,4-triazol-1-yl)methyl]tetrahydrofuran 
• 184378-04-9 C₃₀H₃₂F₂N₆O₂ 
• 1350560-57-4 C₃₇H₄₄F₂N₈O₅ 
• 160709-02-4 ((3R,5R)-5-((1H-1,2,4-triazole-1-yl) methyl)-5-(2,4-difluorophenyl) tetrahydrofuran-3-yl)methanol 
• 1350560-54-1 C₁₄H₁₅F₂N₃O₂*ClH 
• 1350466-82-8 C₁₄H₁₅F₂N₃O₂*ClH 
• 1593266-12-6 ((3R,5R)-5-(bromomethyl)-5-(2,4-difluorophenyl)tetrahydrofuran-3-yl)methanol 

Relevant academic research and scientific papers

Iron-catalyzed regiodivergent alkyne hydrosilylation

Although tremendous effort has been devoted to the development of methods for iron catalysis, few of the catalysts reported to date exhibit clear superiority to other metal catalysts, and the mechanisms of most iron catalysis remain unclear. Herein, we report that iron complexes bearing 2,9-diaryl-1,10-phenanthroline ligands exhibit not only unprecedented catalytic activity but also unusual ligand-controlled divergent regioselectivity in hydrosilylation reactions of various alkynes. The hydrosilylation protocol described herein provides a highly efficient method for preparing useful di- and trisubstituted olefins on a relatively large scale under mild conditions, and its use markedly improved the synthetic efficiency of a number of bioactive compounds. Mechanistic studies based on control experiments and density functional theory calculations were performed to understand the catalytic pathway and the observed regioselectivity.

Method for synthesizing 2-methyl propionate-[(2S)-4-(2,4-diflurophenyl)-2-hydroxymethyl-4-amylene-1-group] ester

The invention provides a method for synthesizing 2-methyl propionate-[(2S)-4-(2,4-diflurophenyl)-2-hydroxymethyl-4-amylene-1-group] ester.The method includes the steps that 1,2,3-trichloropropane is added dropwise to 1,3-difluorobenzene, and aluminum trichloride is added for a reaction; the mixture is added to a hydrochloric acid solution for extraction, and washing is conducted with a saturated NaHCO3 solution, water and saturated salt solution in sequence; anhydrous Na2SO4 is used for drying and filtering, evaporation is conducted for solvent removal, and 1,3-dichloro-2-(2,4-diflurophenyl) propane is obtained; 1,3-dichloro-2-(2,4-diflurophenyl) propane and potassium hydroxide are added to tert butyl alcohol, and reflux is conducted for 3.5-6 h; tert butyl alcohol is removed, ice water is added, the mixture is neutralized with hydrochloric acid at the temperature of 5 to -5 DEG C to be neutral, dichloromethane is used for three times of extraction, anhydrous Na2SO4 is used for drying and filtering, a distillation product is dissolved in DMSO, a product obtained after diethyl malonate and diethyl malonate react are added and a product obtained after lithium chloride and sodium borohydride react are added and dissolved in methylbenzene, and sodium bicarbonate, Novo SP 435 esterifying enzymes and isobutyric anhydride are added for a reaction; the target product is obtained after washing, crystallization and drying are conducted.The synthesis path is shown in the description.

Method for synthesizing 2-[2-(2,4-difluorophenyl)-2-propylene-1-yl]-1,3-propylene glycol

The invention discloses a method for synthesizing 2-[2-(2,4-difluorophenyl)-2-propylene-1-yl]-1,3-propylene glycol. The method comprises the following steps: dropwise adding 1,2,3-trichloropropane into 1,3-difluorobenzene; 20-40min later, adding aluminium trichloride; keeping reactions for 0.5-1.5h at 5-(-5) DEG C; heating to 20-45 DEG C and keeping reactions for 1.5-3h; adding the product into a hydrochloric acid solution and extracting; washing once using saturated NaHCO3 solution, water and saturated saline solution in sequence; drying with anhydrous Na2SO4 and filtering; evaporating to remove the solvent to obtain 1,3-dichloro-2-(2,4-difluorophenyl)propane; adding 1,3-dichloro-2-(2,4-difluorophenyl)propane and potassium hydroxide into tert-butyl alcohol, and enabling backflow for 3.5-6h; removing the tert-butyl alcohol; adding ice water and neutralizing to neutrality using hydrochloric acid at 5-(-5) DEG C; extracting using dichloromethane for three times; drying using anhydrous Na2SO4 and filtering; dissolving the evaporation and distillation product in DMSO, and adding diethyl malonate and hydroxide for reactions; and enabling the obtained product to react with lithium chloride and sodium borohydride to obtain a target product, wherein the synthesis path is shown in the specification.

Synthesis method of 2-[2-(2,4-diflurophenyl)-2-propen-1-yl)-1,3-propanediol

The invention relates to a synthesis method of 2-[2-(2,4-diflurophenyl)-2-propen-1-yl)-1,3-propanediol. The synthesis method comprises the following steps: mixing 2-chloromethyl epoxy propane with 1,3-difluorobenzene to perform reaction under an effect of catalyst to obtain 2-(2,4-diflurophenyl)-1-chloro-3-propanol; mixing 2-(2,4-diflurophenyl)-1-chloro-3-propanol with potassium hydrogen sulfate and chlorobenzene to perform reaction to obtain 1-(1-chloromethylvinyl)-2,4-difluorobenzene; enabling 1-(1-chloromethylvinyl)-2,4-difluorobenzene to react with diethyl malonate to obtain a product 2-[2-(2,4-diflurophenyl)propenyl]-1,3-diethyl malonate; dissolving 2-[2-(2,4-diflurophenyl)-2-propen-1-yl]-1,3-diethyl malonate in mixed solvent formed by isopropanol and water to react with borohydride to obtain a target product 2-[2-(2,4-diflurophenyl)-2-propen-1-yl)-1,3-propanediol; a synthesis route is as shown in the accompanying drawing.

Synthesis method of 2-[2-(2,4-diflurophenyl)-2-propylene-1-yl]-1,3-propylene glycol

The invention relates to a synthesis method of 2-[2-(2,4-diflurophenyl)-2-propylene-1-yl]-1,3-propyl glycol. The synthesis method comprises the following steps: mixing 3-chloro-1,2-propyl glycol with 1,3-difluorphenyl, adding a catalyst, reacting for 6-10 hours at room temperature, heating to 50-70 DEG C, and reacting for 2-4 hours; adding obtained mixture into hydrochloric acid solution at the temperature ranging from -5 DEG C to 5 DEG C, uniformly stirring, extracting for 3-5 times by taking dichloromethane as an extracting agent, and washing extract liquor once with saturated NaHCO3 solution, water and saturated saline solution; drying with anhydrous Na2SO4 and filtering, and evaporating dichloromethane to obtain 1-chloro-2-(2,4-diflurophenyl)-3-propyl glycol; adding 1-chloro-2-(2,4-diflurophenyl)-3-propyl glycol and potassium hydrogen sulphate into chlorobenzene, heating and refluxing for 10-16 hours; washing to be neutral, drying with anhydrous Na2SO4, then filtering, dissolving a distillation product into DMSO, adding diethyl malonate and hydroxide, reacting, and then carrying out reaction on the obtained products with lithium chloride and sodium borohydride, so that the target product is obtained, wherein a synthesis route is described in the specification.

Concise Synthesis of 1,3-Diacetoxy-2-[2′-(2′′,4′′-difluorophenyl)prop-2′-en-1′-yl]propane: An Intermediate for Posaconazole

A concise process of 1,3-diacetoxy-2-[2′-(2″,4″-difluorophenyl)prop-2′-en-1′-yl]propane has been developed. Diethyl malonate was C-alkylated with 2,3-dichloropropene and then the ester groups were reduced by LiAlH4 followed by acylation to provide 2-(2′-chloroprop-2′-en-1′-yl)-1,3-diacetoxypropane. The chloropropene was finally coupled with 2,4-difluorophenylmagnesium bromide and catalyzed by Fe(acac)3 to afford the title compound in good total yield. GRAPHICAL ABSTRACT.

Purification of Posaconazole Intermediates

The present invention relates to a process for the purification of chiral compounds, in particular to the purification of a chiral compound of formula (XI) which may be used as intermediate for the preparation of antifungal agents, preferably posaconazole.

PROCESS FOR THE PREPARATION OF A CHIRAL COMPOUND

The present invention relates to a process for the preparation of a compound of formula (V), in particular posaconazole, wherein said process comprises the steps of (1) providing a mixture comprising a compound of formula (IV), a protic solvent system, and a suitable base; and (2) heating the mixture of (1) to obtain a mixture comprising the compound of formula (V).

PROCESS FOR THE PREPARATION OF A CHIRAL COMPOUND

The present invention relates to a process for the preparation of a compound of formula (V), in particular posaconazole, wherein said process comprises the steps of (1) providing a mixture comprising a compound of formula (IV), a protic solvent system, and a suitable base; and (2) heating the mixture of (1) to obtain a mixture comprising the compound of formula (V).

PREPARATION OF POSACONAZOLE INTERMEDIATES

The present invention relates to process for the preparation of a chiral compound of formula (IX) or a salt thereof, wherein Y1and Y2 are independently F or C1, preferably F, the crystalline compound of formula (IX) as such, and its use for the preparation of an antifungal agent.