124627-86-7

Basic information

• Product Name: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE
• Synonyms: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE
• CAS NO: 124627-86-7
• Molecular Formula: C₁₂H₁₁F₂N₃O
• Molecular Weight: 251.2320464
• Mol File: 124627-86-7.mol

Chemical Properties

• Boiling Point: 371.6±52.0 °C(Predicted)
• Appearance: /
• Density: 1.41±0.1 g/cm3(Predicted)
• Storage Temp.: Amber Vial, Refrigerator
• Solubility: Chloroform (Sparingly), Methanol (Sparingly)
• PKA: 2.75±0.10(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE(124627-86-7)
• EPA Substance Registry System: 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE(124627-86-7)

Safety Data

• Hazardous Substances Data: 124627-86-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE is used as a key intermediate in the synthesis of sulfur-containing antifungal azoles. Its unique structure contributes to the development of effective antifungal agents that target various fungal pathogens, providing a valuable tool in the fight against fungal infections.
The compound's role in the synthesis of antifungal azoles is significant, as these azoles are known for their broad-spectrum antifungal activity. They are commonly used to treat a wide range of fungal infections, including those caused by Candida, Aspergillus, and other pathogenic fungi. By serving as an intermediate in the synthesis of these azoles, 1-[(2R,3S)-2-(2,4-DIFLUORO-PHENYL)-3-METHYL-OXIRANYLMETHYL]-1H-[1,2,4]TRIAZOLE plays a crucial role in the development of new and improved antifungal medications.

Upstream product

• 132507-89-2 (2R,3S)-2-(2,4-Difluoro-phenyl)-1-[1,2,4]triazol-1-yl-butane-2,3-diol 
• 124-63-0 methanesulfonyl chloride 
• 126918-20-5 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,2,3-butanetriol 
• 132563-81-6 1-(2,4-difluorophenyl)-2-(tetrahydropyranyloxy)propan-1-one 
• 126918-19-2 (2S,3S)-2-(2,4-Difluoro-phenyl)-3-(tetrahydro-pyran-2-yloxy)-butane-1,2-diol 
• 126918-18-1 (2S^*,3R^*)-2-(2,4-Difluorophenyl)-1-(dimethylisopropoxysilyl)-3-(tetrahydropyran-2-yloxy)-2-butanol 
• 126918-21-6 (2R^*,3R^*)-2-(2,4-Difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol 
• 132507-77-8 Trifluoro-acetic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 124627-86-7 (2R^*,3S^*)-2-(2,4-Difluorophenyl)-3-methyl-2-<(1H-1,2,4-triazol-1-yl)methyl>oxirane 
• 132507-89-2 threo-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol 
• 126945-34-4 Methanesulfonic acid (1S,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 41253-21-8 sodium triazole 
• 1829-92-1 triethylsulfonium iodide 
• 86404-63-9 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazolyl)ethanone 

Downstream Products

• 126917-48-4 (2R,3R)-3-Azido-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 
• 135272-34-3 (2R,3R)-2-(2,4-difluorophenyl)-3-mercapto-1-[1H-1,2,4-triazol-1-yl]-2-butanol 
• 132507-77-8 Trifluoro-acetic acid (1R,2S)-2-(2,4-difluoro-phenyl)-2-hydroxy-1-methyl-3-[1,2,4]triazol-1-yl-propyl ester 
• 150803-24-0 (2R,3R)-2-(2,4-difluorophenyl)-3-(2H-tetrazol-2-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 

Relevant articles and documents

Asymmetric Catalytic Epoxidation of Terminal Enones for the Synthesis of Triazole Antifungal Agents

An enantioselective epoxidation of α-substituted vinyl ketones was realized to construct the key epoxide intermediates for the synthesis of various triazole antifungal agents. The reaction proceeded efficiently in high yields with good enantioselectivities by employing a chiral N,N′-dioxide/ScIII complex as the chiral catalyst and 35% aq. H2O2 as the oxidant. It enabled the facile transformation for optically active isavuconazole, efinaconazole, and other potential antifungal agents.

NOVEL METHOD FOR PREPARATION OF EPOXYTRIAZOLE DERIVATIVES

The present invention relates to novel processes for preparing epoxytriazole derivatives. The method of claim 1, further comprising the step of adding a base to the intermediate compound. The present invention relates to an epoxytriazole derivative and a manufacturing method thereof. Chemical Formula 1. Here, Ar denotes C. 6 -C10 Aryl group or C aryl group2 -C9 The aryl group 1 -4 is substituted or unsubstituted, and when 2 or more halogen is substituted, the heteroaryl group may be the same as or different from each other, and the heteroaryl group is represented by 1 -4 fluorine, chlorine, or C. 1 -C3 Substituted or unsubstituted alkyl groups, and fluorine, chlorine, or C. 1 -C3 When more than 2 substituents are substituted, each of these substituents may be the same or different and may be different from each other. The A is C. 1 -C3 Represents an alkyl group, and the R represents an alkyl group. 1 And R2 Is a methyl group or an ethyl group.

PROCESS FOR PRODUCING EPOXY ALCOHOL COMPOUND

A compound represented by formula (II): (where Ar represents a phenyl group optionally substituted by 1 to 3 substituents selected from the group consisting of a halogen atom and a trifluoromethyl group, and R represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms) is produced by step A: reacting trimethyl oxosulfonium salt or trimethyl sulfonium salt with a base in a solvent, and removing the resulting solid to obtain a trimethyl oxosulfonium ylide solution or a trimethyl sulfonium ylide solution; and step B: reacting a compound represented by formula (I): and the solution obtained in step A, and the compound represented by formula (II) can be derived to a compound represented by formula (V): that is useful for production of an antifungal agent.

Design, synthesis, and structure-activity relationship studies of novel triazole agents with strong antifungal activity against Aspergillus fumigatus

The incidence of invasive fungal infections has dramatically increased for several decades. In order to discover novel antifungal agents with broad spectrum and anti-Aspergillus efficacy, a series of novel triazole derivatives containing 1,2,3-benzotriazin-4-one was designed and synthesized. Most of the compounds exhibited stronger in vitro antifungal activities against tested fungi than fluconazole. Moreover, 6m showed comparable antifungal activity against seven pathogenic strains as voriconazole and albaconazole, especially against Aspergillus fumigatus (MIC = 0.25 μg/ml), and displayed moderate antifungal activity against fluconazole-resistant strains of Candida albicans. A clear SAR study indicated that compounds with groups at the 7-position resulted in novel antifungal triazoles with more effectiveness and a broader-spectrum.

Triazole alcohol derivative, and preparation method and application thereof

The invention relates to a triazole alcohol derivative, and a preparation method and an application thereof. The chemical structure of the triazole alcohol derivative is represented by formula I, A inthe formula I represents a benzene ring or a substituted benzene ring, and the substituent group of the substituted benzene ring can be located at each position of the benzene ring, is monosubstituted or polysubstituted, and is selected from: a) halogen which is F, Cl, Br or I; b) an electron-withdrawing group, wherein the electron withdrawing group is a cyano group, a nitro group or a trifluoromethyl group; c) a C1-4 low alkyl group or a halogen-substituted low alkyl group; and d) a C1-4 low alkoxy group or a halogen-substituted low alkoxy group. The compound has the advantages of high antifungal activity, low toxicity, wide antibacterial spectrum and the like, and can be used for preparing antifungal medicines.

METHOD FOR PREPARATION OF EFINACONAZOLE IN IONIC LIQUID MEDIUM

The present invention relates to a novel method for preparation of efinaconazole in an ionic liquid medium, the method comprising: reacting 1-[[(2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole, and 4-methylenepiperidine or an organic chemically acceptable salt thereof, wherein the 4-methylenepiperidine or the organic chemically acceptable salt thereof is anionized on a base; and performing a coupling reaction with the 1-[[(2R,3S)-2-(2,4-difluorophenyl)-3-methyloxiranyl]methyl]-1H-1,2,4-triazole in the presence of an ionic liquid compound. The present invention uses an ionic liquid instead of an organic solvent when preparing efinaconazole, thereby reducing related substances compared to the conventional method, shortens the reaction time, thereby making it possible to easily obtain the final compound, efinaconazole, with high purity and high yield, and may be very suitably used for mass production.

Method for preparing efinaconazole intermediate

The invention discloses a method for preparing an efinaconazole intermediate. The method comprises the following step: in a solvent, performing Sharpless asymmetric dihydroxylation on a compound as shown in the formula 2 under the actions of a chiral catalyst, an oxidant and a co-oxidant to prepare a compound as shown in the formula 3, wherein R is halogen or 1,2,4-triazolyl, and R is hydrogen or methyl. The method is green and environment-friendly, high in security, mild in condition, low in cost, simple in step, high in yield and suitable for industrial application. The formula 2 and the formula 3 are as shown in the description.

Efinaconazole, preparation method of efinaconazole intermediate and efinaconazole intermediate

The invention discloses efinaconazole, a preparation method of an efinaconazole intermediate and the efinaconazole intermediate. A preparation method of efinaconazole comprises the following step: in a solvent, under the action of a reducing agent, performing reductive amination reaction on a compound shown in the formula 4 and a compound shown in the formula B. The invention also provides the efinaconazole intermediate shown in the formula 4 and the preparation method thereof, and the preparation method comprises the following step: performing oxidizing reaction on a compound shown in the formula 3 to obtain the compound shown in the formula 4. A preparation method of the compound shown in the formula 3 comprises the following step: in a solvent, performing Sharpless asymmetric dihydroxylation on a compound shown in the formula 2 under the actions of a chiral catalyst, an oxidant and a co-oxidant. The efinaconazole and the preparation method of the efinaconazole intermediate are green and environment-friendly, high in security, mild in condition, low in cost, simple in step, high in yield and suitable for industrial application. The formulas 2, 3, 4 and B are as shown in the description.

Synthetic method of efinaconazole intermediate

The invention relates to a synthetic method of an efinaconazole intermediate and discloses a synthetic method of the efinaconazole intermediate (2R, 3S)-2-(2, 4-difluorophenyl)-3-methyl-2-((1H-1, 2, 4 triazol-group) methyl) ethylene oxide. The preparation method comprises the following steps: synthesizing alpha-(1H-1, 2, 4 triazol)-2, 4-difluoroacetophenone by substitution reaction of alpha-halogenated-2, 4-difluoroacetophenone and 1H-1, 2, 4-triazole, then reacting with a sulfur ylide reagent, and synthesizing 2-(2, 4-difluorophenyl)-3-methyl-2-((1H-1, 2, 4 triazol-group) methyl) ethylene oxide. The synthetic method has the advantages that the used materials are low in price and easy in obtaining, the conditions are mild, the operation is simple, the environmental pollution is less and the production cost is low, and the synthetic method is suitable for industrial production.

A preparation method of the midbody sets up lucky Kang Zuo (by machine translation)

The invention relates to the field of pharmaceutical technology, in particular to a method of preparing intermediates of sets up lucky Kang Zuo, comprising the following steps: D, L - methyl lactate, morpholine, 3, 4 - methoxychroman reaction, with 2, 4 - difluoro bromobenzene reagent reaction to obtain compound III format; compound III in the catalyst under the catalysis of the B L - menthol and triphenylphosphine, by the asymmetric kohl Chaikefusiji reaction to obtain the chiral compound IV; compound IV with 1, 2, 4 - triazole reaction, and then removing the water Cheng Huan, get sets up lucky Kang Zuo key intermediate compound V, this invention uses the D, L - lactic acid methyl ester, by adding the catalyst induction to generate chiral center, greatly reducing the reaction of the raw material cost, high yield, high purity, easy controlled, is suitable for industrial production. (by machine translation)