17825-58-0

Usage

Uses

Used in Organic Synthesis:
2,3-Diphenylcycloprop-2-ene-1-carboxylic acid is used as a building block in organic synthesis for the development of complex organic molecules. Its unique cyclopropane ring and phenyl groups provide opportunities for further functionalization and the creation of diverse chemical entities.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 2,3-Diphenylcycloprop-2-ene-1-carboxylic acid is used as a key intermediate in the synthesis of new drugs. Its reactivity and structural features allow for the design of molecules with specific biological activities, targeting various therapeutic areas.
Used in Drug Discovery:
2,3-Diphenylcycloprop-2-ene-1-carboxylic acid is employed as a starting material in drug discovery processes. Its unique structural elements can be exploited to design and optimize lead compounds with improved pharmacological properties, such as potency, selectivity, and drug-likeness.
Used in Material Science:
Beyond its applications in pharmaceuticals, 2,3-Diphenylcycloprop-2-ene-1-carboxylic acid can also be utilized in the development of new materials with specific properties. Its cyclopropane ring and phenyl groups can be incorporated into polymers, coatings, or other materials to impart unique characteristics, such as stability, reactivity, or selectivity.

InChI:InChI=1/C16H12O2/c17-16(18)15-13(11-7-3-1-4-8-11)14(15)12-9-5-2-6-10-12/h1-10,15H,(H,17,18)

Synthetic route

ethyl 2,3-diphenylcycloprop-2-enecarboxylate (7382-06-1) → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; methanol; water at 20℃; for 48h; Hydrolysis;	95%
Stage #1: ethyl 2,3-diphenylcycloprop-2-enecarboxylate With water; potassium hydroxide In methanol at 20℃; for 48h; Stage #2: With hydrogenchloride In water pH=1;	93%

diazoacetic acid ethyl ester (623-73-4) + diphenyl acetylene (501-65-5) → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
(i) Cu, (heating), (ii) KOH; Multistep reaction;

diphenyl acetylene (501-65-5) + bis(1,3,2-dioxaborol-2-yl)dicobaltatetrahedrane → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / Cu-bronze 2: 95 percent / KOH / tetrahydrofuran; methanol; H2O / 48 h / 20 °C View Scheme

diphenyl acetylene (501-65-5) + thiocyanato → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: rhodium acetate dimer / CH2Cl2 / 35 °C 2: KOH / methanol / 4 h / Heating View Scheme

diphenyl acetylene (501-65-5) → 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: Cu / 0.25 h / 105 °C 2: KOH / methanol; H2O / 1 h / Heating View Scheme

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + benzyl bromide (100-39-0) → 2,3-Diphenyl-cycloprop-2-enecarboxylic acid benzyl ester (99838-01-4)

Conditions	Yield
With N(Et)4(1+)*(2-pyrrolidone-anion) In N,N-dimethyl-formamide for 1h; Ambient temperature;	99%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → 2,3-diphenyl-2-cyclopropene-1-carbonyl chloride (6415-58-3)

Conditions	Yield
With oxalyl dichloride In chloroform for 48h; Ambient temperature; further reagent: SOCl2;	92%
With thionyl chloride	90%
With thionyl chloride

N-hydroxyphthalimide (524-38-9) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → N-(2,3-diphenyl-2-cyclopropenylcarbonyloxy)phthalimide (234075-38-8)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide Substitution;	87%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → N-(2,3-diphenylcycloprop-2-enyl)urea

Conditions	Yield
Stage #1: 2,3-diphenylcycloprop-2-enecarboxylic acid Stage #2: With ammonia	86%

diazomethane (186581-53-3, 908094-01-9) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → methyl 1,5-diphenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-endo-6-carboxylate + methyl 1,5-diphenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-exo-6-carboxylate

Conditions	Yield
In diethyl ether at -10℃; for 480h;	A 14% B 73%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + 1-oxo-2-(1-pyrrolin-1-ylium)-1H-indene-3-olat (15365-97-6, 109159-92-4) → (±)-1′,3′-dioxo-1a,6b-diphenyl-1a,1′,3′,4,5,6,6a,6b-octahydro-1H-spiro[cyclopropa[a]pyrro-lizine-2,2′-indene]-1-carboxylic acid

Conditions	Yield
In methanol at 25℃; for 10h; diastereoselective reaction;	71%

L-leucine (61-90-5) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-isobutyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	68%

glycylglycine (556-50-3) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4S,5S,6R)-4-[(carboxymethyl)carbamoyl]-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
With acetic acid In methanol; water for 12h; Reflux; diastereoselective reaction;	63%

indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + phenylglycin (2835-06-5) → (±)-(1R,4R,5S,6R)-1',3'-dioxo-1,4,5-triphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-inden]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	61%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → 1,2-dophenylcyclopropenylim perchlorate (37647-36-2)

Conditions	Yield
With perchloric acid; acetic anhydride In water at 0℃;	59%
With perchloric acid; acetic anhydride at 0℃; Inert atmosphere;	59%
With perchloric acid; acetic anhydride

2-amino-hexanoic acid (616-06-8) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-butyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	51%

glycine-glycine-glycine (556-33-2) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-4-({2-[(carboxymethyl)amino]-2-oxoethyl}carbamoyl)-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
With acetic acid In methanol; water for 12h; Reflux; diastereoselective reaction;	50%

2-aminooctanoic acid (644-90-6) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-hexyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	42%

L-phenylalanine (63-91-2) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-benzyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	39%

L-valine (72-18-4) + indan-1,2,3-trione hydrate (485-47-2) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → (±)-(1R,4R,5S,6R)-4-isopropyl-1',3'-dioxo-1,5-diphenyl-1',3'-dihydro-3-azaspiro[bicyclo[3.1.0]hexane-2,2'-indene]-6-carboxylic acid

Conditions	Yield
In methanol; water for 10h; Reflux; diastereoselective reaction;	22%

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + phenylmagnesium bromide → 1-Benzoyl-2,3-diphenyl-cycloprop-2-en (2892-41-3)

Conditions	Yield
(i) (COCl)2, (ii) /BRN= 4720968/, Et2O; Multistep reaction;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → cis,cis-1,2-Diphenyl-cyclopropan-carbonsaeure-(3) (123121-31-3)

Conditions	Yield
With hydrogen; Lindlar's catalyst

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + acetonitrile (75-05-8) → 5-methyl-1,2-diphenyl-6-oxa-4-aza-spiro[2.4]hepta-1,4-dien-7-one (19402-90-5)

Conditions	Yield
With triphenylmethyl perchlorate Ambient temperature;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + acecyclone (641-57-6) → 9-Carboxy-7,8,10,11-tetraphenyl-9H-cycloheptaacenaphthalin (106437-16-5)

Conditions	Yield
In xylene Heating;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + sodium methylate (124-41-4) → Methyl-N-(1,2-diphenyl-cyclopropenyl-(3))-carbamat (17825-60-4)

Conditions	Yield
Multistep reaction;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + triphenylmethyl perchlorate → 1.2-Diphenyl-3-triphenylmethyl-cyclopropenylium-perchlorat

Conditions	Yield
With lithium carbonate

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → 1,2-Diphenyl-cyclopropenyl-(3)-hexafluorophosphat

Conditions	Yield
With hexafluorophosphoric acid; acetic anhydride

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) + dimethyl amine (124-40-3) → N.N-Dimethyl-N'-<2.3-diphenyl-2-cyclopropenyl>-harnstoff (17825-62-6)

Conditions	Yield
Multistep reaction;

5,5-Dimethyl-1-pyrroline N-oxide (3317-61-1) + 2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → C22H22NO3

Conditions	Yield
In benzene Addition; UV-irradiation;

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → methyl 3,5-diphenyl-1,4-dihydropyridazine-4-carboxylate (60220-49-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 14 percent / diethyl ether / 480 h / -10 °C 2: sodium methoxide / methanol / 0.08 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 73 percent / diethyl ether / 480 h / -10 °C 2: 96 percent / sodium methoxide / methanol / 0.08 h / 20 °C View Scheme

2,3-diphenylcycloprop-2-enecarboxylic acid (17825-58-0) → 6,6 dimethyl-3-(3-hydroxypropyl)thio-1-(thiazol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one

Conditions	Yield
Multi-step reaction with 3 steps 1: 14 percent / diethyl ether / 480 h / -10 °C 2: sodium methoxide / methanol / 0.08 h / 20 °C 3: 95 percent / aq. potassium permanganate / acetone / 0.5 h View Scheme
Multi-step reaction with 3 steps 1: 73 percent / diethyl ether / 480 h / -10 °C 2: 96 percent / sodium methoxide / methanol / 0.08 h / 20 °C 3: 95 percent / aq. potassium permanganate / acetone / 0.5 h View Scheme

Upstream product

• 7382-06-1 ethyl 2,3-diphenylcycloprop-2-enecarboxylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 501-65-5 diphenyl acetylene 

Downstream Products

• 2892-41-3 1-Benzoyl-2,3-diphenyl-cycloprop-2-en 
• 123121-31-3 cis,cis-1,2-Diphenyl-cyclopropan-carbonsaeure-⁽³⁾ 
• 99838-01-4 2,3-Diphenyl-cycloprop-2-enecarboxylic acid benzyl ester 
• 17825-65-9 1,2-Diphenyl-cyclopropenyl-⁽³⁾-acetat 
• 17825-66-0 1.2-Diphenyl-cyclopropenyl-⁽³⁾-benzoat 
• 19402-91-6 N-<1,2-Diphenyl-3-carboxy-cyclopropen-(1)-yl-(3)>-acetamid 
• 19402-92-7 N-<1,2-Diphenyl-3-aethoxycarbonyl-cyclopropen-(1)-yl-(3)>-acetamid 
• 17825-67-1 1.2-Diphenyl-cyclopropenyl-⁽³⁾-p-nitro-benzoat 
• 17825-61-5 N--1,2-diphenyl-cyclopropenyl-(3)-amin 
• 17825-59-1 C₁₇H₁₄N₂O₃ 
• 65103-96-0 bis(2,3-diphenyl-2-cyclopropenyl)ether 
• 641-44-1 tribenzoylmethane 
• 2892-44-6 (2,3-diphenylcycloallyl)(phenyl)methanol 

Relevant academic research and scientific papers

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Copper-catalysed addition of ethyl diazoacetate to diphenylacetylene and hydrolysis gives 1,2-diphenylcyclopropane-3-carboxylic acid (18b).Conversion to the acid chloride (18c) and reduction with lithium aluminium tri-tert-butoxy hydride gives 1,2-dipheny