61826-40-2

Usage

Uses

Used in Fragrance and Flavor Industry:
(2-phenylcyclopropyl)methanol is utilized as a key ingredient in the creation of fragrances and flavors, capitalizing on its pleasant aroma to enhance the sensory experience of consumer products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical sector, (2-phenylcyclopropyl)methanol serves as an intermediate in the synthesis of various drugs, contributing to the development of new medicinal compounds.
Used in Agrochemical Production:
(2-phenylcyclopropyl)methanol also plays a role in the agrochemical industry, where it is used as an intermediate in the production of pesticides and other agricultural chemicals, supporting crop protection and yield enhancement.
Used in Chemical Research and Development:
(2-phenylcyclopropyl)methanol is employed in the field of chemical research and development for exploring its potential applications, including its insecticidal and antimicrobial properties, which could lead to innovative solutions in pest control and antimicrobial treatments.

InChI:InChI=1/C10H12O/c11-7-9-6-10(9)8-4-2-1-3-5-8/h1-5,9-11H,6-7H2

Upstream product

• 1126-76-7 1,2-Epoxy-4-phenylbutane 
• 946-38-3 ethyl 2-phenylcyclopropylcarboxylate 
• 75-11-6 diiodomethane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 74-95-3 1,1-dibromomethane 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 20030-70-0 methyl 2-phenylcyclopropane-1-carboxylate 
• 100-42-5 styrene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 100-52-7 benzaldehyde 
• 104-54-1 3-Phenylpropenol 
• 908094-04-2 phenyldiazomethane 
• 107-18-6 allyl alcohol 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 

Downstream Products

• 90841-13-7 (3-phenylcyclopropyl)methyl bromide 
• 823180-02-5 (2-(2,2-diiodovinyl)cyclopropyl)benzene 
• 34271-31-3 trans-2-phenylcyclopropanecarbaldehyde 
• 34271-30-2 rac-(1S,2R)-2-phenylcyclopropanecarbaldehyde 
• 139492-31-2 (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane 
• 186183-64-2 (1S,2R)-1-formyl-2-phenylcyclopropane 
• 167612-65-9 (1R,2S)-1-formyl-2-phenylcyclopropane 
• 29667-46-7 (1S,2R)-2-phenylcyclopropylmethanol 
• 17364-45-3 cis-(2-phenylcyclopropyl)methyl acetate 
• 132587-07-6 1-phenylbut-3-enyl acetate 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 107224-37-3 toluene-4-sulfonic acid 2-phenylcyclopropylmethyl ester 
• 331726-86-4 1-Phenyl-2-acetoxymethyl-cyclopropan 

Relevant academic research and scientific papers

Kinetic isotope effects implicate two electrophilic oxidants in cytochrome P450-catalyzed hydroxylations

Intramolecular kinetic isotope effects (KIEs) were determined for cytochrome P450-catalyzed hydroxylation reactions of methyl-dideuterated trans-2-phenylcyclopropylmethane-d2 (1-d2), which gives two products from oxidation of the methyl group, trans-2-phenylcyclopropylmethanol (2) and 1-phenyl-3-buten-1ol (3). In oxidations of each enantiomer of 1-d2 with three P450 enzymes (CYP2B1, CYPΔ2E1, and CYPΔ2E1 T303A), the apparent intramolecular KIEs were different for products 2 and 3 in all cases and different for each enzyme-substrate combination. In oxidations of each enantiomer of undeuterated 1-d0 and trideuteriomethyl 1-d3 by CYP2B1 and CYPΔ2E1, the ratio of products 2/3 decreased for 1-d3 in comparison to 1-d0 in all cases. The results require multiple pathways for P450-catalyzed hydroxylation and are consistent with the two-oxidants model, where hydroxylation is effected by both the hydroperoxy-iron species and the iron-oxo species. The results are not consistent with predictions of the two-states model for P450-catalyzed hydroxylations, where oxidations occur from a low-spin state and a high-spin state of iron-oxo. Copyright

Donor-Acceptor Bicyclopropyls as 1,6-Zwitterionic Intermediates: Synthesis and Reactions with 4-Phenyl-1,2,4-triazoline-3,5-dione and Terminal Acetylenes

The bicyclopropyl system activated by incorporation of donor and acceptor groups in the presence of Lewis acids was used as a synthetic equivalent of 1,6-zwitterions. Opening of both cyclopropane rings in 2′-aryl-1,1′-bicyclopropyl-2,2-dicarboxylates (D-A bicyclopropyl, ABCDs) in the presence of GaI3 + Bu4N+GaI4- results in 5-iodo-5-arylpent-2-enylmalonates as products of HI formal 1,6-addition to the bicyclopropyl system. The use of GaCl3 or GaBr3 as a Lewis acid and terminal aryl or alkyl acetylenes as 1,6-zwitterion interceptors allows the alkyl substituent to be grown to give the corresponding acyclic 7-chloro(bromo)-hepta-2,6-dienylmalonates. The reaction of ABCDs with 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) catalyzed by Yb(OTf)3 also results in the opening of both cyclopropane rings. The reaction products are tetrahydropyridazine derivatives - (7,9-dioxo-1,6,8-triazabicyclo[4.3.0]non-3-en-2-ylmethyl)malonates - containing one more PTAD moiety in the malonyl group.

5,6,7,8-Tetrahydro-1,6-naphthyridine Derivatives as Potent HIV-1-Integrase-Allosteric-Site Inhibitors

A series of 5,6,7,8-tetrahydro-1,6-naphthyridine derivatives targeting the allosteric lens-epithelium-derived-growth-factor-p75 (LEDGF/p75)-binding site on HIV-1 integrase, an attractive target for antiviral chemotherapy, was prepared and screened for activity against HIV-1 infection in cell culture. Small molecules that bind within the LEDGF/p75-binding site promote aberrant multimerization of the integrase enzyme and are of significant interest as HIV-1-replication inhibitors. Structure-activity-relationship studies and rat pharmacokinetic studies of lead compounds are presented.

Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism

A titanium-catalyzed mono-decyanation of geminal dinitriles is reported. The reaction proceeds under mild conditions, tolerates numerous functional groups, and can be applied to quaternary malononitriles. A corresponding desulfonylation is demonstrated as well. Mechanistic experiments support a catalyst-controlled cleavage without the formation of free radicals, which is in sharp contrast to traditional stoichiometric radical decyanations. The involvement of two TiIII species in the C?C cleavage is proposed, and the beneficial role of added ZnCl2 and 2,4,6-collidine hydrochloride is investigated.

Asymmetric Reductive Carbocyclization Using Engineered Ene Reductases

Ene reductases from the Old Yellow Enzyme (OYE) family reduce the C=C double bond in α,β-unsaturated compounds bearing an electron-withdrawing group, for example, a carbonyl group. This asymmetric reduction has been exploited for biocatalysis. Going beyond its canonical function, we show that members of this enzyme family can also catalyze the formation of C?C bonds. α,β-Unsaturated aldehydes and ketones containing an additional electrophilic group undergo reductive cyclization. Mechanistically, the two-electron-reduced enzyme cofactor FMN delivers a hydride to generate an enolate intermediate, which reacts with the internal electrophile. Single-site replacement of a crucial Tyr residue with a non-protic Phe or Trp favored the cyclization over the natural reduction reaction. The new transformation enabled the enantioselective synthesis of chiral cyclopropanes in up to >99 % ee.

Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2- b]pyridazines

In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor-acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in a consecutive manner. In addition, a monodecarboxylation reaction of hexahydropyrrolo[1,2-b]pyridazine was achieved with a good yield.

Olefin-Migrative Cleavage of Cyclopropane Rings through the Nickel-Catalyzed Hydrocyanation of Allenes and Alkenes

A nickel-catalyzed hydrocyanation triggered by hydronickelation of the carbon-carbon double bonds of allenes followed by cyclopropane cleavage is described. The observed regio- and stereochemistries in the products are strongly influenced by the initial hydronickelation step, and allenyl- and methylenecyclopropanes reacted smoothly to promote the cleavage of cyclopropane. In contrast, this cleavage was not observed with vinylidenecyclopropanes, because the initial hydronickelation does not give a suitable intermediate for cleavage of the cyclopropanes. (Figure presented.).

Temporary Generation of a Cyclopropyl Oxocarbenium Ion Enables Highly Diastereoselective Donor-Acceptor Cyclopropane Cycloaddition

A novel formal [3+2] cycloaddition of cyclopropylacetals and aldehydes was developed, and the resulting trisubstituted tetrahydrofurans display three new chiral centers formed with highly diastereoselectivity. This method is stereocomplementary to most previously reported cycloadditions of malonate diesters, relies on the transient generation of cyclopropyl oxocarbenium ions, proceeds under mild conditions, and is based on the concept of temporary activation of an otherwise inert protecting group. Hide-and-seek with a dipole: A novel formal [3+2] cycloaddition of cyclopropylacetals and aldehydes was developed. This reaction affords trisubstituted tetrahydrofurans displaying three newly formed chiral centers with high diastereoselectivity. The reaction relies on the transient generation of cyclopropyl oxocarbenium ions under mild conditions and is based on the concept of temporary activation of an otherwise inert protecting group.

Lewis Basic Sulfide Catalyzed Electrophilic Bromocyclization of Cyclopropylmethyl Amide

A Lewis basic sulfide catalyzed electrophilic bromocyclization of cyclopropylmethyl amide has been developed. The catalytic protocol is applicable to both 1,1- and 1,2-substituted cyclopropylmethyl amides, giving oxazolines and oxazines in good yields and excellent diastereoselectivity.

A Novel Cathode Material for Cathodic Dehalogenation of 1,1-Dibromo Cyclopropane Derivatives

Leaded bronze turned out to be an excellent cathode material for the dehalogenation reaction of cyclopropanes without affecting the strained molecular entity. With this particular alloy, beneficial properties of lead cathodes are conserved, whereas the corrosion of cathode is efficiently suppressed. The solvent in the electrolyte determines whether a complete debromination reaction is achieved or if the process can be selectively stopped at the monobromo cyclopropane intermediate. The electroorganic conversion tolerates a variety of functional groups and can be conducted at rather complex substrates like cyclosporine A. This approach allows the sustainable preparation of cyclopropane derivatives.