14799-82-7

Usage

Synthesis

Triphenylphosphine (3.9 g, 14.8 mmoles) was placed into a 300 mL round bottom flask, equipped with a condenser which was cooled with tap water. Dry benzene (100 mL) (distilled over sodium/benzophenone) was cannulated into the reaction vessel, and a positive pressure of argon and magnetic stirring were maintained throughout the reaction sequence. Cyclopropylmethyl bromide (2.0 g, 14.8 mmoles) was added to the solution via syringe. The reaction mixture was heated at reflux for 10 days producing insoluble cyclopropylmethyltriphenylphosphonium bromide.

InChI:InChI=1/C22H22P.BrH/c1-4-10-20(11-5-1)23(18-19-16-17-19,21-12-6-2-7-13-21)22-14-8-3-9-15-22;/h1-15,19H,16-18H2;1H/q+1;/p-1

Upstream product

• 7051-34-5 cyclopropylcarbinyl bromide 
• 603-35-0 triphenylphosphine 
• 2516-33-8 Cyclopropylmethanol 

Downstream Products

• 14799-59-8 (2-cyclopropylethene-1,1-diyl)dibenzene 
• 16958-36-4 cis-1-Cyclopropyl-2-(o-hydroxyphenyl)-ethylen 
• 16958-37-5 trans-1-Cyclopropyl-2-(o-hydroxyphenyl)-ethylen 
• 16958-38-6 Cyclohexyliden-cyclopropyl-methan 
• 14799-60-1 1-phenyl-2-cyclopropylethylene 
• 16958-34-2 (Z)-1-cyclopropyl-2-phenyl ethylene 
• 16958-35-3 (E)-1-cyclopropyl-2-phenyl ehtylene 
• 929041-98-5 3-(2-cyclopropylvinyl)-5-[methyl(methylsulfonyl)amino]benzoic acid 
• 928319-22-6 8-cyclopropylmethyl-2-(2,4-difluorophenyl)imidazo[1,2-a]pyrazine 
• 1071990-94-7 (Z)-1-(4-cyclopropylbut-3-enyl)-3-methoxybenzene 
• 1071990-96-9 (Z)-1-[(5-cyclopropylpent-4-enyloxy)methyl]benzene 
• 1071990-97-0 (Z)-1-tert-butyl-4-(4-cyclopropyl-2-methylbut-3-enyl)benzene 

Relevant academic research and scientific papers

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A biosynthetically inspired route to substituted furans using the Appel reaction: Total synthesis of the furan fatty acid F5

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LIQUID CRYSTAL COMPOUND AND LIQUID CRYSTAL MIXTURE CONTAINING CYCLOPROPYL

PROBLEM TO BE SOLVED: To provide a compound represented by the general formula I. SOLUTION: There is provided a liquid crystal compound containing cyclopropyl represented by the formula I which has an excellent use value since it has not only a positive or negative dielectric anisotropy(?ε), a proper refractive index anisotropy (?n), a relatively high clear point (CP), outstanding low temperature miscibility with the other liquid crystals and a low rotational viscosity but also has excellent stability to ultraviolet rays and excellent stability to high temperatures. The compound is applied for the preparation of a positive or negative liquid crystal compound and can be used for a passive or active matrix display. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPOandINPIT

Reductive and brominative termination of alkenol cyclization in aerobic cobalt-catalyzed reactions

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β SECRETASE INHIBITOR

Disclosed is a compound represented by the formula (1) below which is useful as a drug for treating Alzheimer's disease, or a pharmaceutically acceptable salt thereof. (1) [In the formula, R1 represents a group represented by the following formula (2): (2) (wherein X represents a nitrogen atom or a group expressed as C(R5); Y represents a nitrogen atom or a group expressed as C(R6); and R5 and R6 independently represent a hydrogen atom or the like) or the like; m represents an integer of 1-6; L1 represents a single bond or the like; R2 represents a hydrogen atom, a substituted or unsubstituted alkyl group or the like; R3 represents a hydrogen atom or the like; L2 represents a single bond or the like; and R4 represents a hydrogen atom, a substituted or unsubstituted aryl group or the like.]

Pheromones, 89.- Wittig Syntheses of Alkyl-Branched and Cyclic Analogs of (Z)-5-Decenyl Acetate, the Sex Pheromone of Agrotis segetum (Lepitoptera: Noctuidae)

By means of (Z)-selective Wittig olefination alkyl-branched and cyclic analogs of (Z)-5-decenyl acetate, the sex pheromone of the turnip moth, Agrotis segetum (Lepidoptera: Noctuidae), have been synthesized. Key Words: Pheromones / (Z)-5-decenyl acetate / Wittig reactions / Agrotis segetum

Opening of a Cyclopropyl Ring in (Diphenylcyclopropyl)alkenes Promoted by Electron Transfer from Potassium 4,4'-Di-tert-butylbiphenyl Radical Anion and X-ray and Theoretical Calculations of the Structure of (Z)-1,2-Bis(trans-2,trans-3-diphenylcyclopropyl)ethene

We have prepared the (diphenylcyclopropyl)alkenes 1a-c and studied their reductions, using potassium 4,4'-di-tert-butylbiphenyl radical anion (DBB.-) as an electron source.Spectra analyses of the reaction products reveal that the double bond of the alkene stayed intact, whereas the cyclopropyl moiety was cleaved to provide alkenes 2a-c.When the reaction was carried out with a simple cyclopropylalkene without phenyl substituents (1e), the starting material was fully recovered.This indicates that the opening of the cyclopropyl ring in the alkenes is promoted by electron transfer from potassium DDB.- onto the phenyl rings attached to the cyclopropyl moiety.Two mechanisms were considered: (1) opening of the cyclopropyl via a cyclopropylcarbinyl to homoallylcarbinyl radical rearrangement (CPCRR) with potassium DBB.- as the le- reductant, with electron transfer to the phenyl rings attached to the cyclopropyl moiety, and (2) 2e- transfer to the phenyl rings and opening of the cyclopropyl moiety via an anionic rearrangement(CPCAR). (Z)-1-(trans-2,trans-3-Diphenylcyclopropyl)butene (1c) was used as a model for AM1 calculations which establish that the isomeric form of the radical anion product with opened cyclopropyl ring (1c.- form 1) is about 7 kcal/mol lower in energy than an isomeric form in which the cyclopropyl ring is closed (1c.- form 2).This suggests that the opening of the cyclopropyl ring is likely to happen through CPCRR rather than CPCAR.The X-ray crystal structure of (Z)-1,2-bis(trans-2,trans-3-diphenylcyclopropyl)ethene (1a) shows the two phenyl rings to be completely out of the cyclopropyl ring plane.The average C-C bond distance for the cyclopropyl moiety in the trans-2,trans-3-diphenylcyclopropyl rings is 1.562 Angstroem, which is longer than the average bond distance in unsubstituted cyclopropyl rings.The gas-phase structures as calculated by AM1, PM3, and MNDO molecular orbital methods are all quite similar and agree closely with the X-ray structure.However, MNDO gave more satisfactory results than AM1 and PM3 for bond distances and bond angles and deviated more for torsion angles.The latter is reflected by the relatively large difference in the heat of formations (7 kcal/mol) of the gas-phase fully optimized structure and the X-ray structure.