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Chemical Structure| 23020-15-7

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Product Details of [ 23020-15-7 ]

CAS No. :23020-15-7
Formula : C10H10O2
M.W : 162.19
SMILES Code : O=C([C@@H]1[C@@H](C2=CC=CC=C2)C1)O
MDL No. :MFCD12195831
InChI Key :AHDDRJBFJBDEPW-BDAKNGLRSA-N
Pubchem ID :778517

Safety of [ 23020-15-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 23020-15-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 23020-15-7 ]

[ 23020-15-7 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 23020-15-7 ]
  • [ 29667-50-3 ]
  • 3
  • [ 23020-15-7 ]
  • (+)-trans-2-Phenylcyclopropyliodid [ No CAS ]
  • 6
  • [ 939-90-2 ]
  • [ 23020-15-7 ]
YieldReaction ConditionsOperation in experiment
With ChiralpakAD 5 u; In ethanol; at 35℃; under 75007.5 Torr;Supercritical conditions; Resolution of racemate; Preparative supercritical fluid chromatography (SFC) was performed on a Berger Multigram II operating at 50 mL/min at 35 C. and 100 bar backpressure using stacked injections. The column was a ChiralpakAD 5 u, 250×21 mm. The eluent was CO2 (70%) and ethanol (30%).
  • 7
  • [ 23020-15-7 ]
  • [ 222632-77-1 ]
  • ((1S,2S)-2-Phenyl-cyclopropyl)-[(S)-3-(pyrrolidine-1-carbonyl)-3,4-dihydro-1H-isoquinolin-2-yl]-methanone [ No CAS ]
  • 9
  • (+/-)-trans-2-phenylcyclopropanecarbonitrile [ No CAS ]
  • [ 23020-15-7 ]
  • [ 928054-81-3 ]
  • [ 58641-87-5 ]
  • [ 3471-10-1 ]
  • 10
  • (+/-)-trans-2-phenylcyclopropanecarbonitrile [ No CAS ]
  • [ 23020-15-7 ]
  • [ 58641-87-5 ]
  • [ 3471-10-1 ]
  • 11
  • [ 23020-15-7 ]
  • [ 1013-76-9 ]
  • [ 307952-37-0 ]
  • 12
  • [ 23020-15-7 ]
  • [ 1013-78-1 ]
  • [ 307952-30-3 ]
  • 13
  • [ 131899-86-0 ]
  • [ 23020-15-7 ]
  • 14
  • rac-(1R,2R)-2-phenylcyclopropanecarboxamide [ No CAS ]
  • [ 23020-15-7 ]
  • [ 928054-81-3 ]
  • [ 58641-87-5 ]
  • [ 3471-10-1 ]
  • 15
  • 2-phenyl-cyclopropanecarbonitrile [ No CAS ]
  • [ 23020-15-7 ]
  • [ 58641-87-5 ]
  • [ 3471-10-1 ]
  • 16
  • (1S)-1-formyl-2-phenylcyclopropane [ No CAS ]
  • [ 23020-15-7 ]
  • [ 23020-18-0 ]
  • 17
  • (+/-)-trans-2-phenylcyclopropanecarbonitrile [ No CAS ]
  • [ 23020-15-7 ]
  • [ 58641-87-5 ]
  • [ 3471-10-1 ]
  • trans-2-phenylcyclopropanecarbonitrile [ No CAS ]
  • 18
  • [ 23020-15-7 ]
  • meso-1,2-diphenyl-1,2-diaminoethane [ No CAS ]
  • (1S,2S)-2-Phenyl-cyclopropanecarboxylic acid (2-amino-1,2-diphenyl-ethyl)-amide [ No CAS ]
  • 19
  • [ 23020-15-7 ]
  • [ 473252-82-3 ]
  • (4-{2-[Bis-(4-fluoro-phenyl)-methoxy]-ethyl}-piperidin-1-yl)-((1S,2S)-2-phenyl-cyclopropyl)-methanone [ No CAS ]
  • 20
  • [ 939-90-2 ]
  • [ 23020-15-7 ]
  • [ 3471-10-1 ]
YieldReaction ConditionsOperation in experiment
Resolution of racemate; ±trans-2-phenylcyclopropanecarboxylic acid was separated into constituent enantiomers (Intermediate Y and Z) using chiral SFC. Intermediate Y: 1HNMR (300 MHz, CDC13) δ 1HNMR (300 MHz, CDC13) δ 7.35-7.09 (m, 5H), 2.61 (ddd, 1H), 1.91 (dq, 1H), 1.67 (q, 1H), 1.42 (dq, 1H). ESIMS m/z [M-H]+ 161.2. [a]D24 4 -259.546 (c 0.119, MeOH). Absolute stereochemistry assigned by comparison with literature (JMC 2000, p3923; JMC 2011, p957). Intermediate Z: 1HNMR (300 MHz, CDC13) δ 7.35-7.09 (m, 5H), 2.61 (ddd, 1H), 1.91 (dq, J = 4.8, 3.9, 1H), 1.67 (q, 1H), 1.42 (dq, 1H). ESIMS m/z [M-H]+ 161.2. [a]D245 +249.261 (c 0.102, MeOH). Absolute stereochemistry assigned by comparison with literature (JMC 2000, p3923; JMC 2011, p957).
  • 21
  • (+/-)-trans-2-phenylcyclopropanecarbonitrile [ No CAS ]
  • [ 23020-15-7 ]
  • [ 58641-87-5 ]
  • [ 3471-10-1 ]
  • 22
  • (+/-)-trans-2-phenylcyclopropanecarbonitrile [ No CAS ]
  • [ 23020-15-7 ]
  • [ 928054-81-3 ]
  • [ 58641-87-5 ]
  • [ 3471-10-1 ]
  • 23
  • [ 23020-15-7 ]
  • trans-(S,S)-4-[2-[bis(4-fluorophenyl)methoxy]ethyl]-1-(2-phenylcyclopropylmethyl)piperidine [ No CAS ]
  • 24
  • [ 23020-15-7 ]
  • 4,5-Diphenyl-2-((1S,2S)-2-phenyl-cyclopropyl)-4,5-dihydro-1H-imidazole [ No CAS ]
  • 25
  • [ 23020-15-7 ]
  • (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dimethylphenyl)piperazine [ No CAS ]
  • 26
  • [ 23020-15-7 ]
  • (1S,2S)-trans-1-[(2-phenylcyclopropyl)methyl]-4-(2,4-dichlorophenyl)piperazine [ No CAS ]
  • 27
  • (1SR,2SR)-2-phenylcyclopropanecarbonyl chloride [ No CAS ]
  • [ 23020-15-7 ]
  • 28
  • (1R,2R)-2-Phenyl-cyclopropanecarboxylic acid ((R)-1-phenyl-ethyl)-amide [ No CAS ]
  • [ 23020-15-7 ]
  • 31
  • [ 23020-15-7 ]
  • (1S,2S)-2-phenylcyclopropane-1-carbaldehyde [ No CAS ]
  • 32
  • [ 23020-15-7 ]
  • (1R,2S)-1-(1-propenyl)-2-phenylcyclopropane [ No CAS ]
  • 33
  • [ 23020-15-7 ]
  • (+)-trans-1-(o-Methoxycarbonylphenyl)-2-phenylcyclopropan [ No CAS ]
  • 34
  • [ 928055-00-9 ]
  • [ 23020-15-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; water; In 1,4-dioxane; at 100℃; for 24h; i) trans-(+)-2-Phenyl-cyclopropanecarboxylic acid; A solution of fcans-(+)-2-phenyl-cyclopropanecarboxylic acid (2-hydroxy-1-phenyl- ethyl)-amide (150 mg, 0.534 mmol) in dioxane (5 mL) was added to 3N H2SO4 (5 mL). The mixture was stirred at 100 C for 24 h and then poured into water and extracted with CH2CI2 (x3). The combined organic phases were dried over MgSO4, EPO <DP n="129"/>filtered and concentrated. and all volatiles were removed under vacuum. The crude residue was purified by silica gel column chromatography using a mixture of EtOAc/hexane (1 :2) as an eluent to afford the title compound as colorless solid (73 mg, 84%). 1H NMR (CDCI3): δ (ppm) 10.3 (br. S, 1 H), 7.34-7.22 (m, 3 H), 7.14 (d, 2 H1 J = 7.0 Hz), 2.64 (m, 1 H), 1.93 (m, 1 H), 1.70 (m, 1 H), 1.44 (m, 1 H). 13C NMR (CDCI3): δ (ppm) 180.2, 139.9, 128.9 (2), 127.1 , 126.7 (2), 27.5, 24.4, 17.9. (+)-CO2H, [α]D +374, c 0.55, CHCI3.
  • 35
  • [ 23020-15-7 ]
  • [ 78738-39-3 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride;N,N-dimethyl-formamide; In toluene; at 80℃; for 2.5h; ii) trans-(+)-(2-Phenyl-cyclopropyl)-methylamine hydrochloride; To a solution of /ra/7s-(+)~2-phenyl-cyclopropanecarboxylic acid (60 mg, 0.37 mmol) in toluene (3 ml_) were added dropwise several drops of dimethylformamide and thionyl chloride (0.403 ml_, 5.55 mmol). After stirring at 80 C for 2.5 h, the reaction mixture was concentrated under vacuum. The resulting residue was dissolved in toluene (2 ml_) again, and the solution was added to liquid ammonia (ca. 10 ml_) at - 78 C. After stirring at -78 C for 30 min and then at room temperature for 30 min, CH2CI2 (10 ml) was added to the mixture at -78 C and the resulting mixture was stirred at room temperature overnight. After addition of EtOAc, the mixture was washed with satd. aqueous NH4CI (x2), dried over Na2SO4 and all volatiles were removed under vacuum. The corresponding amide was isolated as pearl yellow powders and further purified by recrystallization from hexane/EtOAc (45 mg).
With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 0.75h; To a solution of (l S,2S)-2-phenyl-cyclopropanecarboxylic acid ( 170 mg, 1.05 mmol) in dichloromethane ( 10 ml ) was added oxallyl dichloride ( 145 mg, 1.2 mmol) followed by a few drops of N, N-dimethylformamide at RT. The reaction mixture was stirred at RT for 45 mins before it was concentrated down and dissolved in dichloromethane (1.5 ml). The solution was added slowly to a solution of (S)-l- (4-bromo-phenyl)-propylamine (250 mg, l.Ommol, HC1 salt) and triethylamine (222 mg, 2.2 mmol) in dichloromethane (10 ml) at 0 C. The resulting reaction mixture was stirred at RT for 1.5h. Water was added and the aqueous layer was extracted by dichloromethane. Organic layer was dried by magnesium sulfate and concentrated. The residue was purified via column chromatography on silica gel to afford (1 S,2S)- 2-phenyl-cyclopropanecarboxylic acid [(S)-l-(4-bromo-phenyl)-propyl]-amide (330 mg, 92%). XH NMR (400 MHz, CHLOROF ORM-d) δ ppm 7.37 (d, J=8.6 Hz, 2 H), 7.15 - 7.23 (m, 2 H), 7.11 (d, J=7.3 Hz, 1 H), 7.08 (d, J=8.3 Hz, 2 H), 6.98 (d, J=7.3 Hz, 2 H), 5.75 (d, J=7.6 Hz, 1 H), 4.77 (q, J=7.5 Hz, 1 H), 2.31 - 2.41 (m, 1 H), 1.65 - 1.81 (m, 2 H), 1.48 - 1.59 (m, 2 H), 1.12 - 1.23 (m, 1 H), 0.82 (t, J=7.4 Hz, 3 H); LRMS ( ESI) (M + 1) = 360.04. Molecular Formula =Ci9H20BrNO.
With oxalyl dichloride; In dichloromethane; at 20℃; for 2.5h; In a dry 100 ml round-bottomed flask was added oxalyl chloride (2.0 ml, 23 mmol) to 8B (0.25 g, 1.5 mmol) in CH2Cl2 at room temperature to give a yellow solution. In 2.5 hours, the reaction was complete. The crude mixture was concentrated in vacuo and residual <n="164"/>PATENT ASKl -5001 -WOTFA was removed azeotropically with toluene 3 times to give the desired product (lS,2S)-2- phenylcyclopropanecarbonyl chloride (8B-1), which was used in the next step without further purification.
 

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