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Chemical Structure| 23020-15-7 Chemical Structure| 23020-15-7

Structure of 23020-15-7

Chemical Structure| 23020-15-7

(1S,2S)-2-Phenylcyclopropanecarboxylic acid

CAS No.: 23020-15-7

4.5 *For Research Use Only !

Cat. No.: A623874 Purity: 98%

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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   1~34

  • 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.
 

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