1-Phenylcyclopropan-1-ol

Base Information

• Chemical Name: 1-Phenylcyclopropan-1-ol
• CAS No.: 29526-96-3
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• Hs Code.: 2906299090
• European Community (EC) Number: 837-532-5
• DSSTox Substance ID: DTXSID30481742
• Nikkaji Number: J88.606H
• Wikidata: Q82317341
• Mol file: 29526-96-3.mol

Synonyms:1-phenylcyclopropan-1-ol;29526-96-3;1-phenylcyclopropanol;Cyclopropanol, 1-phenyl-;1-PHENYL-1-CYCLOPROPANOL;1-phenyl-cyclopropan-1-ol;SCHEMBL7815717;DTXSID30481742;MFCD16840724;AKOS011963349;PB48554;BS-13321;CS-0056020;EN300-84361;D72927

Chemical Property of 1-Phenylcyclopropan-1-ol

Chemical Property:

• PSA: 20.23000
• LogP: 1.66800
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 121

Purity/Quality:

99%, ^*data from raw suppliers

1-Phenylcyclopropanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC1(C2=CC=CC=C2)O

Technology Process of 1-Phenylcyclopropan-1-ol

There total 50 articles about 1-Phenylcyclopropan-1-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + ethylmagnesium chloride (2386-64-3) → 1-phenylcyclopropan-1-ol (29526-96-3)

Guidance literature:

ethylmagnesium chloride; With titanium(IV) isopropylate; In diethyl ether; at -78 ℃; for 1.5h;

benzoic acid methyl ester; In diethyl ether; at 25 ℃; for 10h; Further stages.;

DOI:10.1002/ejoc.200300588

Reference yield: 93.0%

benzoic acid ethyl ester (93-89-0,99341-95-4) + ethylmagnesium bromide (925-90-6) → 1-phenylcyclopropan-1-ol (29526-96-3)

Guidance literature:

With titanium(IV) isopropylate; In diethyl ether; at -78 - 0 ℃; for 0.5h;

Reference yield: 85.0%

1-(benzenesulfonyl)cyclopropanol (1006613-82-6) + phenylmagnesium bromide (100-58-3) → 1-phenylcyclopropan-1-ol (29526-96-3)

Guidance literature:

1-(benzenesulfonyl)cyclopropanol; With methylmagnesium bromide; In tetrahydrofuran; at -78 ℃; for 5h;

phenylmagnesium bromide; In tetrahydrofuran; at -78 - 20 ℃; for 5h;

DOI:10.1021/acs.orglett.0c02303

upstream raw materials:

ethyl bromide

benzoic acid ethyl ester

1-styrenyloxytrimethylsilane

diiodomethane

Downstream raw materials:

3-hydroxy-1-phenylpropan-1-one

1-phenyl-1-trimethylsiloxycyclopropane

1-phenylhexane-1,5-dione

1,5-diphenyl-1,5-pentanedione

Refernces

Rh-Catalyzed cascade C-H activation/C-C cleavage/cyclization of carboxylic acids with cyclopropanols

10.1039/d1cc01778k

The research focuses on the development of a novel Rh(III)-catalyzed cascade reaction involving C–H activation, ring-opening C–C bond cleavage, and cyclization of carboxylic acids with cyclopropanols to synthesize 3-substituted phthalides and a,b-butenolides. This reaction exhibits excellent functional group tolerance and operates under relatively mild conditions, which is significant for the late-stage functionalization of bioactive compounds. The experiments involved optimizing the reaction conditions using ortho-methylbenzoic acid and 1-phenylcyclopropan-1-ol as model substrates, with the best yield achieved using [Cp*RhCl2]2/AgOAc, Cs2CO3, and 4 ? MS in CH3CN solvent at 80°C. The scope of the reaction was explored with various aryl- and alkyl-substituted cyclopropanols and carboxylic acids, yielding the desired products in modest to good yields. Mechanistic studies included kinetic isotope effect experiments, deuterium incorporation experiments, and the examination of potential intermediates, leading to a proposed mechanism involving rhodacycle formation, β-C elimination, β-H elimination, and migratory insertion steps.

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