67074-44-6

Usage

Uses

Used in Fragrance Industry:
Cyclopropanecarboxaldehyde, 2-phenyl(9CI) is used as a key ingredient in the fragrance industry for its sweet, floral scent. It contributes to the creation of various perfumes, colognes, and other scented products, enhancing their overall aroma profile.
Used in Flavor Industry:
In the flavor industry, Cyclopropanecarboxaldehyde, 2-phenyl(9CI) is utilized as a flavoring agent to impart a sweet, floral taste to food and beverage products. Its unique flavor profile adds depth and complexity to a variety of culinary creations.
Used in Pharmaceutical Industry:
Cyclopropanecarboxaldehyde, 2-phenyl(9CI) is employed in the pharmaceutical industry for its potential therapeutic applications. Its chemical properties make it a valuable compound in the development of new drugs and medicinal formulations.
Used in Chemical Synthesis:
As a versatile chemical compound, Cyclopropanecarboxaldehyde, 2-phenyl(9CI) is used in various chemical synthesis processes. Its reactivity and functional groups allow it to be a building block for the production of other complex organic molecules and specialty chemicals.

Upstream product

• 186581-53-3 diazomethane 
• 1021956-61-5 2-(trans-styryl)-3-ethyl-1,3-oxazolidine 
• 110659-58-0 (1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane 
• 936-98-1 ((S)-2-Phenyl-cyclopropyl)-methanol 
• 14371-10-9 (E)-3-phenylpropenal 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 73566-21-9 1-phenyl-2-((tetrahydro-2H-pyran-2-yl)oxy)ethan-1-one 
• 107804-91-1 ((1S,2R)-2-Dimethoxymethyl-cyclopropyl)-benzene 
• 936-98-1 rac-((1S,2R)-2-phenylcyclopropyl)methanol 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 61826-40-2 (2-phenylcyclopropyl)methanol 
• 143618-74-0 trans-(2'-phenylcyclopropyl)methyl benzoylformate 
• 107804-97-7 3-Dimethoxymethyl-5-phenyl-4,5-dihydro-3H-pyrazole 

Downstream Products

• 5685-38-1 2-phenyl-cyclopropanecarboxylic acid 

Relevant academic research and scientific papers

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.

Radical-Cation Vinylcyclopropane Rearrangements by TiO2Photocatalysis

Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations.

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.

Copper(I)- and Mesoionic-Hydroxyamide-Catalyzed Chemoselective Aerobic Oxidation of Primary Benzylic Alcohols

A new aerobic oxidation system consisting of Cu(I)I, 2,2'-bipyridine, N -methyl imidazole, and a mesoionic hydroxyamide was developed, with which selective oxidation of a broad range of benzylic alcohols was achieved.

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.

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.

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.

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.).

Synthesis and cytotoxic activities of goniothalamins and derivatives

Substituted goniothalamins containing cyclopropane-groups were efficiently prepared in high yields and good selectivity. Antiproliferative activity was measured on three human cancer cell lines (A549, MCF-7, HBL-100), to show which of the structural elements of goniothalamins is mandatory for cytotoxicity. We found that the configuration of the stereogenic centre of the δ-lactone plays an important role for cytotoxicity. In our studies only (R)-configured goniothalamins showed antiproliferative activity, whereby (R)-configuration accords to natural goniothalamin (R)-1. Additionally, the δ-lactone needs to be unsaturated whereas our results show that the vinylic double bond is not mandatory for cytotoxicity. Furthermore, with a two-fold in vitro and in vivo strategy, we determined the inhibitory effect of the compounds to the yeast protein Pdr5. Here, we clearly demonstrate that the configuration seems to be of minor influence, only, while the nature of the substituent of the phenyl ring is of prime importance.

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.