1224883-68-4

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-(trifluoromethyl)phenyl)cyclopropan-1-ol is used as a versatile building block for the preparation of various pharmaceuticals. Its unique structure and properties allow for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(4-(trifluoromethyl)phenyl)cyclopropan-1-ol is utilized as a key component in the synthesis of various agrochemicals, contributing to the development of innovative products for agricultural use.
Used in Asymmetric Synthesis:
1-(4-(trifluoromethyl)phenyl)cyclopropan-1-ol is employed as a chiral auxiliary in asymmetric synthesis. Its presence in the reaction can help to control the stereochemistry of the products, leading to the formation of enantiomerically pure compounds with potential applications in various industries, including pharmaceuticals and materials science.
Used in Medicinal Chemistry:
1-(4-(trifluoromethyl)phenyl)cyclopropan-1-ol is also used in medicinal chemistry due to the unique properties imparted by the trifluoromethyl group. This feature can be exploited to design and synthesize new molecules with improved pharmacological profiles.
Used in Materials Science:
1-(4-(trifluoromethyl)phenyl)cyclopropan-1-ol's cyclopropane ring offers opportunities for diversification and functionalization through chemical reactions. This makes it a valuable compound for the development of new materials with specific properties tailored for various applications in the materials science field.

Upstream product

• 1006613-82-6 1-(benzenesulfonyl)cyclopropanol 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 583-02-8 ethyl 4-(trifluoromethyl)benzoate 
• 925-90-6 ethylmagnesium bromide 
• 2967-66-0 methyl 4-(trifluoromethyl)benzoate 
• 188912-47-2 trimethyl((1-(4-(trifluoromethyl)phenyl)vinyl)oxy)silane 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 2386-64-3 ethylmagnesium chloride 
• 1224883-59-3 C₁₆H₁₃F₃O₄S 
• 31729-70-1 bis(iodozinc)methane 

Downstream Products

• 1503565-76-1 4,4,4-trifluoro-1-(4-(trifluoromethyl)phenyl)butan-1-one 

Relevant academic research and scientific papers

NOVEL COMPOUNDS

The invention relates to compounds of formula (I) and to their use in treating or preventing an inflammatory disease or a disease associated with an undesirable immune response: wherein R, R1, R2 and RB are as defined herein.

Catalytic Asymmetric Allylic Substitution with Copper(I) Homoenolates Generated from Cyclopropanols

By using copper(I) homoenolates as nucleophiles, which are generated through the ring-opening of 1-substituted cyclopropane-1-ols, a catalytic asymmetric allylic substitution with allyl phosphates is achieved in high to excellent yields with high enantioselectivity. Both 1-substituted cyclopropane-1-ols and allylic phosphates enjoy broad substrate scopes. Remarkably, various functional groups, such as ether, ester, tosylate, imide, alcohol, nitro, and carbamate are well tolerated. Moreover, the present method is nicely extended to the asymmetric construction of quaternary carbon centers. Some control experiments argue against a radical-based reaction mechanism and a catalytic cycle based on a two-electron process is proposed. Finally, the synthetic utilities of the product are showcased by means of the transformations of the terminal olefin group and the ketone group.

The Cyclopropane Ring as a Reporter of Radical Leaving-Group Reactivity for Ni-Catalyzed C(sp3)-O Arylation

The ability to understand and predict reactivity is essential for the development of new reactions. In the context of Ni-catalyzed C(sp3)-O functionalization, we have developed a unique strategy employing activated cyclopropanols to aid the design and optimization of a redox-active leaving group for C(sp3)-O arylation. In this chemistry, the cyclopropane ring acts as a reporter of leaving-group reactivity, since the ring-opened product is obtained under polar (2e) conditions, and the ring-closed product is obtained under radical (1e) conditions. Mechanistic studies demonstrate that the optimal leaving group is redox-active and are consistent with a Ni(I)/Ni(III) catalytic cycle. The optimized reaction conditions are also used to synthesize a number of arylcyclopropanes, which are valuable pharmaceutical motifs.

Aryl Pyrazoles from Photocatalytic Cycloadditions of Arenediazonium

A photocatalytic synthesis of 1,5-diaryl pyrazoles from arenediazoniums and arylcyclopropanols is reported. The reaction proceeded under mild conditions (rt, 20 min) with catalytic [Ru(bpy)3]2+ under blue-light irradiation and exhibited compatibility with several functional groups (e.g., I, SF5, SO2NH2, N3, CN) and perfect levels of regiocontrol. Mechanistic studies (luminescence spectroscopy, CV, DFT, radical trapping, quantum yield determination) documented an initial oxidative quenching of the excited photocatalyst and the operation of a radical-chain mechanism.

General Synthesis of Cyclopropanols via Organometallic Addition to 1-Sulfonylcyclopropanols as Cyclopropanone Precursors

The addition of organometallic reagents to ketones constitutes one of the most straightforward synthetic approaches to tertiary alcohols. However, due to the absence of a well-behaved class of cyclopropanone surrogates accessible in enantioenriched form, such a trivial synthetic disconnection has received very little attention in the literature for the formation of tertiary cyclopropanols. In this work, we report a simple and high-yielding synthesis of 1-substituted cyclopropanols via the addition of diverse organometallic reagents to 1-phenylsulfonylcyclopropanols, acting here as in situ precursors of the corresponding cyclopropanones. The transformation is shown to be amenable to sp-, sp2-, or sp3-hybridized organometallic C-nucleophiles under mild conditions, and the use of enantioenriched substrates led to highly diastereoselective additions and the formation of optically active cyclopropanols.

Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: Synthesis of: N -arylpyrazoles

A general method for the synthesis of structurally diverse N-arylpyrazoles from readily available cyclopropanols and aryldiazonium salts is disclosed. The reaction was conducted at room temperature within minutes with a broad substrate scope and excellent regioselectivity.

Metal-Free Direct C–H β-Carbonyl Alkylation of Heteroarenes with Cyclopropanols Mediated by K2S2O8

Direct C–H β-carbonyl alkylation of heteroarenes under metal-, acid- and photo-catalyst free conditions has been achieved. A wide scope of substrates, such as various substituted quinolines and isoquinolines, pyridines, pyridazine, benzo[d]thiazole and phenanthroline, underwent the β-carbonyl alkylation efficiently via K2S2O8-mediated ring-opening of cyclopropanols. The corresponding β-heteroarylated ketones were obtained in moderate to excellent yields and gram-scale experiments further demonstrated the practicality of this synthetic protocol. The readily available reagents, mild and environmentally benign conditions make the method extremely attractive. The reaction mechanism is also proposed.

Copper-catalysed ring-opening trifluoromethylation of cyclopropanols

A copper-catalysed ring-opening trifluoromethylation reaction of cyclopropanols has been developed. Various β-trifluoromethyl ketones are obtained in good to excellent yields under mild reaction conditions. The present method also exhibits good functional-group compatibility. The mechanism of this new ring-opening trifluoromethylation reaction was investigated by radical trapping reactions.

Stereospecific construction of chiral tertiary and quaternary carbon by nucleophilic cyclopropanation with bis(iodozincio)methane

The reaction of a ketone having a leaving group at the aposition, such as a,bepoxy ketone or asulfonyloxy ketone, with bis(iodozincio) methane affords a zinc alkoxide of cyclopropanol. The reaction proceeds by nucleophilic addition of the dizinc to the carbonyl group and a sequential intramolecular nucleophilic substitution of the introduced iodozinciomethyl group to the adjacent electrophilic carbon that has a leaving group. When an optically active a,β-epoxy ketone or asulfonyloxy ketone is treated with the dizinc, a zinc alkoxide of cyclopropanol having a chiral tertiary or quaternary carbon in the cyclopropane ring is obtained, and the obtained zinc alkoxide of cyclopropanol acts as a chiral ho-moenolate. When it is treated with an electrophile in the presence of copper cyanide, it gives an optically active a-tertiary or -quaternary ketone that retains high optical purity.