10488-04-7

Upstream product

• 946-38-3 cis-1-ethoxycarbonyl-2-phenylcyclopropane 
• 100-52-7 benzaldehyde 
• 20030-70-0 methyl 2-phenylcyclopropane-1-carboxylate 
• 100-42-5 styrene 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 75-11-6 diiodomethane 
• 104-54-1 3-Phenylpropenol 
• 908094-04-2 phenyldiazomethane 
• 107-18-6 allyl alcohol 
• 939-89-9 (1S*,2R*)-2-phenylcyclopropane-1-carboxylic acid 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 67528-62-5 cis-methyl 2-phenylcyclopropane-1-carboxylate 
• 763126-74-5 (1R,2S)-1,2-di(hydroxymethyl)-2-phenylcyclopropane 

Downstream Products

• 22467-91-0 cis-1-(trans-β-Ethoxycarbonylvinyl)-2-phenylcyclopropan 
• 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 
• 34271-30-2 (1S,2S)-2-phenylcyclopropane-1-carbaldehyde 
• 625389-83-5 (1R,2S)-1-[4-(2,4-dimethylphenyl)piperazyl]carbonyl-2-phenylcyclopropane 
• 307952-37-0 [4-(2,4-Dimethyl-phenyl)-piperazin-1-yl]-((1S,2S)-2-phenyl-cyclopropyl)-methanone 
• 939-89-9 (1R)-1-carboxy-2-phenylcyclopropane 
• 34271-30-2 rac-(1S,2R)-2-phenylcyclopropanecarbaldehyde 

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.

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.

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.

Copper-catalyzed regio- and stereoselective intermolecular three-component oxyarylation of allenes

A copper(II)-catalyzed intermolecular three-component oxyarylation of allenes using arylboronic acids as a carbon source and TEMPO as an oxygen source is described. The reaction proceeded under mild conditions with high regio- and stereoselectivity and functional group tolerance. A plausible reaction mechanism is proposed, involving carbocupration of allenes, homolysis of the intervening allylcopper(II), and a radical TEMPO trap.

Improved zinc-catalyzed simmons-smith reaction: Access to various 1,2,3-trisubstituted cyclopropanes

The Simmons-Smith reaction of zinc carbenoids with alkenes is a powerful method to access cyclopropanes containing various substitution patterns. This work exploits the high reactivity of aryldiazomethanes toward zinc halides to generate aryl-substituted carbenoids catalytically. These carbenoids are able to cyclopropanate various alkenes diastereoselectively, including unfunctionalized substrates such as styrenes. The zinc catalyst can be modified to tolerate the use of free allylic alcohols.

Synthesis of highly functionalized cyclohexenone rings: Rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition

Lead Rh-ole: Highly substituted cyclohexenones were prepared from cyclopropyl-substituted propargyl esters by using a [{Rh(CO)2Cl} 2] catalyst. This metal catalyst promoted the 1,3-acyloxy migration of propargyl esters and a subsequent [5+1] cycloaddition of the resulting allenylcyclopropanes in the presence of CO with high regioselectivity.

Mechanistic studies on au(I)-catalyzed [3,3]-sigmatropic rearrangements using cyclopropane probes

A comparative study of the Au(I)-catalyzed [3,3]-sigmatropic rearrangement of propargylic esters and propargyl vinyl ethers is described. Stereochemically defined cyclopropanes are employed as mechanistic probes to provide new synthetic and theoretical data concerning the reversibility of this type of rearrangement. Factors controlling the structure-reactivity relationship of Au(I)-coordinated allenes have been examined, therebyallowing for controlled access to orthogonal reactivity.

In situ generation of zinc carbenoids from diazo compounds and zinc salts: Asymmetric synthesis of 1,2,3-substituted cyclopropanes

(Chemical Equation Presented) The first enantioselective cyclopropanation of alkenes using zinc carbenoids generated in situ from diazo compounds and zinc salts is reported. This new method allows the highly enantioand diastereoselective synthesis of 1,2,

Construction of a cis-Cyclopropane via Reductive Radical Decarboxylation. Enantioselective Synthesis of cis- and trans-1-Arylpiperazyl-2-phenylcyclopropanes Designed as Antidopaminergic Agents

(1S,2S)-, (1S,2R)-, and (1R,2S)-1-(2,4-Dimethylphenyl)piperazyl-2-phenylcyclopropane (2a, 3, and ent-3, respectively), which were designed as conformationally restricted analogues of haloperidol (1), a clinically effective antipsychotic agent, were synthe