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Chemistry
Organic Building Blocks
Aryls
cyclopentanecarboxylic
1-Phenyl-1-cyclopentanecarboxylic acid
Chemistry
Organic Building Blocks
Aryls
Carboxylic Acids Aliphatic Cyclic Hydrocarbons Benzene Compounds
cyclopentanecarboxylic
cyclopentylbenzene

[ CAS No. 77-55-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 77-55-4
Chemical Structure| 77-55-4
Chemical Structure| 77-55-4
Structure of 77-55-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 77-55-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 77-55-4 ]
Product Citations

Product Details of [ 77-55-4 ]

CAS No. :77-55-4 MDL No. :MFCD00001372
Formula : C12H14O2 Boiling Point : -
Linear Structure Formula :- InChI Key :RHPCYZLXNNRRMB-UHFFFAOYSA-N
M.W : 190.24 Pubchem ID :66167
Synonyms :

Calculated chemistry of [ 77-55-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.42
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.98
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.78
Log Po/w (XLOGP3) : 2.81
Log Po/w (WLOGP) : 2.58
Log Po/w (MLOGP) : 2.47
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.48

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.202 mg/ml ; 0.00106 mol/l
Class : Soluble
Log S (Ali) : -3.25
Solubility : 0.107 mg/ml ; 0.000562 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.15
Solubility : 0.135 mg/ml ; 0.000708 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 77-55-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 77-55-4 ]

* 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 [ 77-55-4 ]

[ 77-55-4 ] Synthesis Path-Downstream   1~108

  • 1
  • [ 1932-03-2 ]
  • [ 77-55-4 ]
  • [ 24158-54-1 ]
Reference： [1]Patent: CH247927,1944,
  • 2
  • [ 77-55-4 ]
  • [ 64-17-5 ]
  • [ 4535-95-9 ]
Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4861,4863
  • 3
  • [ 77-55-4 ]
  • [ 17380-62-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 1h;Reflux; A solution of 1-phenyl cyclopentane carboxylic acid (2 g, 10.5 mmol) in thionyl chloride (20 ml) is heated to reflux for 1 hour after which time all of the starting acid has been consumed. The reaction mixture is concentrated in vacuo and the resulting acid chloride used directly for the synthesis [(tert-butoxy)carbonyl]amino 1-phenylcyclopentane-1-carboxylate, which is prepared from the described acid chloride and N-tert-butoxycarbonyl hydroxylamine according to Scheme 1. (2.4 g, 75%), 1H NMR (250 MHz, CHLOROFORM-d) delta ppm 7.62 (1H, s), 7.18-7.49 (5H, m), 2.63-2.86 (2H, m), 1.93-2.11 (2H, m), 1.71-1.90 (4H, m), 1.45 (9H, s).
Reference： [1]Patent: CH234452,1942,
[2]Doklady Akademii Nauk Armyanskoi SSR,1958,vol. 27,p. 93,96, 97
    Chem.Abstr.,1959,p. 18904
[3]Chemische Berichte,1973,vol. 106,p. 2890 - 2903
[4]Journal of Medicinal Chemistry,1991,vol. 34,p. 3159 - 3164
[5]Journal of Medicinal Chemistry,1994,vol. 37,p. 1964 - 1970
[6]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 1793 - 1805
[7]Journal of the American Chemical Society,2006,vol. 128,p. 78 - 79
[8]Tetrahedron,2008,vol. 64,p. 6979 - 6987
[9]Journal of the American Chemical Society,2008,vol. 130,p. 14058 - 14059
[10]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3561 - 3571
[11]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3507 - 3510
[12]Patent: US2011/136827,2011,A1 .Location in patent: Page/Page column 40
[13]Journal of the American Chemical Society,2014,vol. 136,p. 898 - 901
[14]Journal of the American Chemical Society,2015,vol. 137,p. 5193 - 5198
[15]Chemistry - A European Journal,2018,vol. 24,p. 8315 - 8319
[16]Patent: US2404588,1944,
[17]Angewandte Chemie - International Edition,2019,vol. 58,p. 6756 - 6760
    Angew. Chem.,2019,vol. 131,p. 6828 - 6832,5
[18]Journal of Medicinal Chemistry,2020,vol. 63,p. 5956 - 5971
  • 4
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentanecarboxylic acid <i>p</i>-toluidide [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1941,vol. 63,p. 3538
  • 5
  • [ 77-57-6 ]
  • [ 77-55-4 ]
Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 6464 - 6469
[2]Japan P. 3427 &lt;1952&gt;; C.A. 1954 3999,
[3]Zhurnal Obshchei Khimii,1952,vol. 22,p. 2189,2191; engl. Ausg. S. 2247, 2248
[4]Doklady Akademii Nauk Armyanskoi SSR,1958,vol. 27,p. 93,96, 97
    Chem.Abstr.,1959,p. 18904
[5]Journal of Organic Chemistry,1959,vol. 24,p. 616,618, 619
[6]Helvetica Chimica Acta,1971,vol. 54,p. 868 - 897
[7]Journal of applied chemistry of the USSR,1965,vol. 38,p. 148 - 153
    Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation),1965,vol. 38,p. 159 - 166
[8]Chemische Berichte,1973,vol. 106,p. 2890 - 2903
[9]Bulletin de la Societe Chimique de France,1967,p. 3722 - 3729
[10]Helvetica Chimica Acta,1977,vol. 60,p. 1091 - 1123
  • 6
  • [ 21573-69-3 ]
  • [ 77-55-4 ]
YieldReaction ConditionsOperation in experiment
91% With potassium sulfite; copper(l) chloride; potassium bromide; In cyclohexane; at 160℃; for 8h; A reaction vessel equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel was charged with 230 ml of a 40% sodium bisulfite solution, 0.15 mol of stannous chloride, a stirring speed of 160 rpm, raise the solution temperature to 55 C, slowly add phenylacetaldehyde (2) 0.63mol, 1,4-diaminobutane (4) 0.73mol, dropping time control in 3h, raising the temperature of the solution to 65 C, stirring the reaction for 9h, add the mass fraction of 20% potassium bromide solution 230ml, reduce the solution temperature to 15 C, precipitation of oily liquid, for the intermediate product (3); The intermediate product (3) was washed 9 times with a mass fraction of 65%, The oil was added to 300 ml of a 45% cyclohexane solution, adding potassium bromide solution 130ml, cuprous chloride0.23 mol, potassium Sulfite 0.26mo 1, raise the solution temperature to 160 C, reflux 8 h, add 2L mass fraction of 15% sodium chloride solution, molecular sieve bleaching, hot filter, The filtrate was added with a mass fraction of 35% oxalic acid to adjust the pH of the solution to 2, Precipitation of white solid, suction filtration, sodium sulfate solution washing, the mass fraction of 75% toluene washing, activated alumina dehydration, recrystallization in nitromethane, crystal 1-phenylcyclopentanecarboxylic acid 108.93g, the yield of 91%
Reference： [1]Patent: CN105622384,2016,A .Location in patent: Paragraph 0015; 0016
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1928,vol. 187,p. 46
    Bulletin de la Societe Chimique de France,1931,vol. &lt;4&gt; 49,p. 1834
[3]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1928,vol. 187,p. 46
    Bulletin de la Societe Chimique de France,1931,vol. &lt;4&gt; 49,p. 1834
  • 7
  • [ 77-55-4 ]
  • [ 141-43-5 ]
  • 1-phenyl-cyclopentanecarboxylic acid-(2-diethylamino-ethylamide) [ No CAS ]
Reference： [1]Patent: US2437545,1945,
  • 8
  • [ 77-55-4 ]
  • [ 100-35-6 ]
  • [ 77-22-5 ]
Reference： [1]Patent: CH240169,1942,
  • 9
  • [ 77-55-4 ]
  • [ 615-36-1 ]
  • 1-phenyl-cyclopentanecarboxylic acid-(2-bromo-anilide) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1941,vol. 63,p. 3538
  • 10
  • [ 110-52-1 ]
  • [ 16537-09-0 ]
  • [ 77-55-4 ]
Reference： [1]Roczniki Chemii,1973,vol. 47,p. 89 - 98
  • 11
  • [ 64-18-6 ]
  • [ 10487-96-4 ]
  • [ 77-55-4 ]
Reference： [1]Bulletin de la Societe Chimique de France,1961,p. 2319 - 2324
  • 12
  • [ 77-55-4 ]
  • [ 44747-21-9 ]
  • [ 74-88-4 ]
  • [ 29885-29-8 ]
Reference： [1]Canadian Journal of Chemistry,1965,vol. 43,p. 3119 - 3128
  • 13
  • [ 110-91-8 ]
  • [ 77-55-4 ]
  • [ 76277-98-0 ]
Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2709 - 2716
  • 14
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • [ 4535-96-0 ]
YieldReaction ConditionsOperation in experiment
sulfuric acid;Heating / reflux; To a solution of methyl [1- (2-FLUOROPHENYL) CYCLOPENTANECARBOXYLIC] acid [(LOG,] 52.56 mmol) in anhydrous methanol was added 1 mL of the concentration of sulfuric acid. The mixture was refluxed for overnight. The mixture was neutralized to pH 4-5 with sodium carbonate. The solvent was evaporated. The residue was dissolved in ethyl acetate [(50] mL), washed with brine (3 x 10 mL), dried over [MGS04.] The crude product was used for the next reaction without further purification.
Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 2598 - 2600
[2]Journal of Medicinal Chemistry,1991,vol. 34,p. 3159 - 3164
[3]Patent: WO2003/103604,2003,A2 .Location in patent: Page 65
  • 15
  • [ 77-55-4 ]
  • [ 917-54-4 ]
  • [ 4046-09-7 ]
Reference： [1]Chemische Berichte,1981,vol. 114,p. 3831 - 3854
[2]Helvetica Chimica Acta,1977,vol. 60,p. 1091 - 1123
  • 16
  • [ 77-55-4 ]
  • [ 37517-78-5 ]
  • [ 154382-30-6 ]
Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2943 - 2949
  • 17
  • [ 77-55-4 ]
  • [ 114955-85-0 ]
  • (S)-1-(4-Methoxy-3-methyl-benzyl)-5-(1-phenyl-cyclopentanecarbonyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid methyl ester [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 3248 - 3260
  • 18
  • [ 77-55-4 ]
  • [ 541-41-3 ]
  • [ 408539-39-9 ]
Reference： [1]Pharmaceutical Chemistry Journal,1988,vol. 22,p. 695 - 698
    Khimiko-Farmatsevticheskii Zhurnal,1988,vol. 22,p. 1091 - 1094
[2]Pharmaceutical Chemistry Journal,1987,vol. 21,p. 115 - 119
    Khimiko-Farmatsevticheskii Zhurnal,1987,vol. 21,p. 186 - 191
[3]Pharmaceutical Chemistry Journal,1988,vol. 22,p. 390 - 393
    Khimiko-Farmatsevticheskii Zhurnal,1988,vol. 22,p. 572 - 575
  • 19
  • 1-Methyl-1-(1-phenyl-cyclopentanecarbonyloxymethyl)-pyrrolidinium; chloride [ No CAS ]
  • [ 77-55-4 ]
Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 474 - 480
  • 20
  • [ 77-55-4 ]
  • [ 59115-90-1 ]
YieldReaction ConditionsOperation in experiment
93% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 18h;Reflux; To a stirred solution of 1-phenylcyclo-1-pentane-carboxylic acid (5.00 g, 26.3 mmol) in 25 mL of THF at 0C was added LAH (52 mL , 52 mmol, 1M) in THF. The reaction mixture was slowly warmed to rt and then refluxed for 18 h. The reaction was quenched according to the Fieser procedure: careful addition of 2 mL of water; 6 mL of 15% NaOH in water; and 2 mL of water. The biphasic mixture was diluted with 100 mL of ether and the granular white solid filtered off. The ether fraction was dried over Na2SO4 and evaporated to give 4.30 g (93%) of the Step 1 compound.
Reference： [1]Patent: EP2272825,2015,B1 .Location in patent: Paragraph 0333; 0334
[2]Journal of Organic Chemistry,1994,vol. 59,p. 6464 - 6469
[3]Journal of Medicinal Chemistry,1991,vol. 34,p. 3159 - 3164
[4]Organic Letters,2008,vol. 10,p. 1465 - 1468
[5]Journal of Organic Chemistry,2012,vol. 77,p. 3049 - 3059
[6]Organic Letters,2017,vol. 19,p. 2626 - 2629
[7]Organic and Biomolecular Chemistry,2019,vol. 17,p. 8408 - 8416
  • 21
  • [ 77-55-4 ]
  • [ 52648-77-8 ]
Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1996,vol. 38,p. 471 - 481
[2]Journal of Organic Chemistry,1998,vol. 63,p. 3814 - 3820
[3]Patent: WO2003/99276,2003,A1 .Location in patent: Page 236-237
YieldReaction ConditionsOperation in experiment
REFERENCE EXAMPLE 19 In a stream of argon, 60% sodium hydride was dissolved in 10 ml of tetrahydrofuran, and the solution was mixed with 2.0 g of benzyl cyanide, stirred for 1 hour at room temperature, further mixed with 3.69 g of 1,4-dibromobutane and again stirred for 16 hours at room temperature. The reaction mixture was mixed with water and ethyl acetate, and the resulting organic layer was separated, washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under a reduced pressure, the thus obtained residue was subjected to silica gel column chromatography, and the resulting hexane elude was mixed with 45 ml of sulfuric acid and subjected to 24 hours of heating under reflux. After cooling down to room temperature, the reaction solution was mixed with ice water and ethyl acetate to separate water layer which was subsequently mixed with concentrated hydrochloric acid and ethyl acetate, and the resulting organic layer was separated, washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. By removing the solvent by distillation under a reduced pressure, 978 mg of 1-phenylcyclopentanecarboxylic acid was obtained. Physicochemical properties 1 H-NMR (delta ppm in CDCl3, TMS internal standard): 1.84-2.08 (m, 8H), 7.21-7.45 (m, 4H) MS (EI): 190 (M+)
REFERENCE EXAMPLE 20 Using 2.0 g of benzyl cyanide and 3.9 g of 1,5-dibromopentane, the procedure of Reference Example 19 was repeated to obtain 980 mg of 1-phenylcyclopentane-carboxylic acid. Physicochemical properties 1 H-NMR (delta ppm in CDCl3, TMS internal standard): 1.26-1.87 (m, 10H), 7.22-7.52 (m, 4H) MS (EI): 204 (M+)
  • 25
  • [ 77-55-4 ]
  • [ 31076-84-3 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(4-Acetyl-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 26
  • [ 77-55-4 ]
  • [ 4659-45-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(2,6-Dichloro-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 27
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • [ 31076-84-3 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(4-Acetyl-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 28
  • [ 77-55-4 ]
  • [ 14002-51-8 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-[(Biphenyl-4-carbonyl)-amino]-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 29
  • [ 77-55-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • [ 33863-86-4 ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(4-Butoxy-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 30
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • [ 4659-45-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(2,6-Dichloro-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 31
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • [ 14002-51-8 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-[(Biphenyl-4-carbonyl)-amino]-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 32
  • [ 25054-53-9 ]
  • [ 77-55-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-[(Benzo[1,3]dioxole-5-carbonyl)-amino]-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 33
  • [ 67-56-1 ]
  • [ 77-55-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • [ 33863-86-4 ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-(4-Butoxy-benzoylamino)-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 34
  • [ 67-56-1 ]
  • [ 25054-53-9 ]
  • [ 77-55-4 ]
  • 3-Amino-5-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid; compound with methanesulfonic acid [ No CAS ]
  • aminoacyl chlorotrityl resin [ No CAS ]
  • (S)-2-{3-[(Benzo[1,3]dioxole-5-carbonyl)-amino]-5-[(1-phenyl-cyclopentanecarbonyl)-amino]-benzoylamino}-3-phenyl-propionic acid methyl ester [ No CAS ]
Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 5317 - 5320
  • 35
  • [ 77-55-4 ]
  • [ 81677-60-3 ]
  • [ 220880-33-1 ]
Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 1679 - 1682
  • 36
  • [ 77-55-4 ]
  • [ 423774-22-5 ]
  • 9-(3,5-dideoxy-3-[(1-phenylcyclopentyl)carbonyl]amino}-β-D-xylofuranosyl)-N6-cyclopentyladenine [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1845 - 1852
  • 37
  • [ 77-55-4 ]
  • [ 225528-11-0 ]
  • (S)-3-(2'-Methoxy-biphenyl-4-yl)-2-[(1-phenyl-cyclopentanecarbonyl)-amino]-propionic acid [ No CAS ]
Reference： [1]Bioorganic and medicinal chemistry letters,2002,vol. 12,p. 2141 - 2144
  • 38
  • [ 77-55-4 ]
  • [ 100-51-6 ]
  • 1-phenyl-cyclopentanecarboxylic acid benzyl ester [ No CAS ]
Reference： [1]Angewandte Chemie - International Edition,2002,vol. 41,p. 4117 - 4119
  • 39
  • [ 77-55-4 ]
  • [ 455311-42-9 ]
  • (+)-KF4 [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 281 - 284
  • 40
  • [ 77-55-4 ]
  • [ 444904-20-5 ]
  • (1R,4S,5S,7R)-(-)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicylo-[3.3.1]non-7-yl-(1-phenyl-1-cyclopentane)carboxamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 281 - 284
  • 41
  • [ 77-55-4 ]
  • (1SR,4RS,5RS,7SR)-(+/-)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicylo-[3.3.1]nonan-7-amine [ No CAS ]
  • (1SR,4RS,5RS,7SR)-(+/-)-5-(3-hydroxyphenyl)-4-methyl-2-(3-phenylpropyl)-2-azabicylo-[3.3.1]non-7-yl-(1-phenyl-1-cyclopentane)carboxamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 281 - 284
  • 42
  • N-(3-phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline [ No CAS ]
  • [ 77-55-4 ]
  • 1-phenylcyclopentanecarboxylic acid [4a-(3-methoxyphenyl)-8a-methyl-2-(3-phenylpropyl)octahydroisoquinolin-6-yl]amide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 8182 - 8193
  • 43
  • [ 77-55-4 ]
  • [ 252002-18-9 ]
  • C28H36N2O [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 847 - 849
  • 44
  • [ 77-55-4 ]
  • [ 95-54-5 ]
  • 1-phenylcyclopentanecarboxylic acid (2-aminophenyl)amide [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4490 - 4518
  • 45
  • [ 186581-53-3 ]
  • [ 77-55-4 ]
  • [ 4535-96-0 ]
Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7419 - 7433
  • 46
  • (+)-(1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]nonan-7-amine [ No CAS ]
  • [ 77-55-4 ]
  • N-[(1S,4R,5R,7S)-5-(3-isopropoxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]non-7-yl]-1-phenylcyclopentanecarboxamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5597 - 5609
  • 47
  • [ 911422-98-5 ]
  • [ 77-55-4 ]
  • [ 911423-02-4 ]
Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5597 - 5609
  • 48
  • [ 77-55-4 ]
  • N-[(1S,4R,5R,7S)-5-(3-hydroxyphenyl)-4-methyl-2-azabicyclo[3.3.1]non-7-yl]-1-phenyl-1-cyclopentacarboxamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5597 - 5609
  • 49
  • [ 77-55-4 ]
  • (+)-N-[(1S,4R,5R,7S)-5-(3-hydroxyphenyl)-2,4-dimethyl-2-azabicyclo[3.3.1]non-7-yl]-1-phenyl-1-cyclopentanecarboxamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5597 - 5609
  • 50
  • [ 77-55-4 ]
  • (+)-N-{(1S,4R,5R,7S)-5-(3-hydroxyphenyl)-4-methyl-2-[3-(2-methylphenyl)prop-2-en-1-yl]-2-azabicyclo[3.3.1]non-7-yl}-1-phenylcyclopentanecarboxamide [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5597 - 5609
  • 51
  • [ 77-55-4 ]
  • 2-(1-phenyl-cyclopentyl)-4,5-dihydro-1<i>H</i>-imidazole [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 7419 - 7433
  • 52
  • [ 77-55-4 ]
  • 2-(1-phenyl-cyclopentyl)-1<i>H</i>-benzoimidazole [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4490 - 4518
  • 53
  • [ 77-55-4 ]
  • [ 874895-84-8 ]
Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 78 - 79
  • 54
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-o-tolylcyclopentyl)oxazoline [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 78 - 79
  • 55
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-(2-ethylphenyl)cyclopentyl)oxazoline [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 78 - 79
  • 56
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-(2-propylphenyl)cyclopentyl)oxazoline [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 78 - 79
  • 57
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-(2-butylphenyl)cyclopentyl)oxazoline [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 78 - 79
  • 58
  • [ 77-55-4 ]
  • 4,4-dimethyl-2-(1-(2-octylphenyl)cyclopentyl)oxazoline [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 78 - 79
  • 59
  • [ 77-55-4 ]
  • 1-phenylcyclopentanecarboxylic acid 2-[1-(3,5-bis(1-methylethoxy)phenyl)-3-ethyl-7-methoxyisoquinolin-6-yloxy]ethyl ester [ No CAS ]
Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 1793 - 1805
  • 60
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • [ 91640-63-0 ]
Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1996,vol. 38,p. 471 - 481
  • 61
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • [ 135569-28-7 ]
Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1996,vol. 38,p. 471 - 481
  • 62
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • 1-(4-Iodo-phenyl)-cyclopentanecarbonyl chloride [ No CAS ]
Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1996,vol. 38,p. 471 - 481
  • 63
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • [ 135569-31-2 ]
Reference： [1]Journal of labelled compounds and radiopharmaceuticals,1996,vol. 38,p. 471 - 481
  • 64
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • [ 95424-44-5 ]
Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 6464 - 6469
  • 65
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • 20(4-phenylpiperidinyl)ethyl 1-phenylcyclopentanecarboxylate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1964 - 1970
  • 66
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • 2-(4-phenylpiperazinyl)ethyl 1-phenylcyclopentanecarboxylate [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1964 - 1970
  • 67
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentane-carboxylic acid-(1)-amide [ No CAS ]
  • 1-Phenyl-cyclopentanecarboxylic acid 3-(4-phenyl-piperidin-1-yl)-propyl ester [ No CAS ]
Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 1964 - 1970
  • 68
  • [ 77-55-4 ]
  • [ 108098-25-5 ]
Reference： [1]Pharmaceutical Chemistry Journal,1987,vol. 21,p. 115 - 119
    Khimiko-Farmatsevticheskii Zhurnal,1987,vol. 21,p. 186 - 191
  • 69
  • [ 77-55-4 ]
  • [ 122348-06-5 ]
Reference： [1]Pharmaceutical Chemistry Journal,1988,vol. 22,p. 695 - 698
    Khimiko-Farmatsevticheskii Zhurnal,1988,vol. 22,p. 1091 - 1094
  • 70
  • [ 77-55-4 ]
  • [ 115780-93-3 ]
Reference： [1]Pharmaceutical Chemistry Journal,1988,vol. 22,p. 390 - 393
    Khimiko-Farmatsevticheskii Zhurnal,1988,vol. 22,p. 572 - 575
  • 71
  • [ 77-55-4 ]
  • [ 80606-91-3 ]
Reference： [1]Chemische Berichte,1981,vol. 114,p. 3831 - 3854
  • 72
  • [ 77-55-4 ]
  • [ 80606-01-5 ]
Reference： [1]Chemische Berichte,1981,vol. 114,p. 3831 - 3854
  • 73
  • [ 77-55-4 ]
  • [ 136089-22-0 ]
Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 3159 - 3164
  • 74
  • [ 77-55-4 ]
  • [ 136089-15-1 ]
Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 3159 - 3164
  • 75
  • [ 77-55-4 ]
  • [ 136089-24-2 ]
Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 3159 - 3164
  • 76
  • [ 77-55-4 ]
  • [ 136089-20-8 ]
Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 3159 - 3164
  • 77
  • [ 77-55-4 ]
  • [ 77-22-5 ]
Reference： [1]Doklady Akademii Nauk Armyanskoi SSR,1958,vol. 27,p. 93,96, 97
    Chem.Abstr.,1959,p. 18904
[2]Patent: CH234452,1942,
[3]Journal of the American Chemical Society,2015,vol. 137,p. 5193 - 5198
  • 78
  • [ 77-55-4 ]
  • [ 4339-96-2 ]
Reference： [1]Doklady Akademii Nauk Armyanskoi SSR,1958,vol. 27,p. 93,96, 97
    Chem.Abstr.,1959,p. 18904
  • 79
  • [ 77-55-4 ]
  • [ 4339-97-3 ]
Reference： [1]Doklady Akademii Nauk Armyanskoi SSR,1958,vol. 27,p. 93,96, 97
    Chem.Abstr.,1959,p. 18904
[2]Patent: US2404588,1944,
  • 80
  • [ 140-29-4 ]
  • [ 77-55-4 ]
Reference： [1]Zhurnal Obshchei Khimii,1952,vol. 22,p. 2189,2191; engl. Ausg. S. 2247, 2248
[2]Doklady Akademii Nauk Armyanskoi SSR,1958,vol. 27,p. 93,96, 97
    Chem.Abstr.,1959,p. 18904
[3]Journal of Organic Chemistry,1959,vol. 24,p. 616,618, 619
  • 81
  • [ 77-55-4 ]
  • [ 15811-02-6 ]
Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4861,4863
  • 82
  • [ 77-55-4 ]
  • [ 59358-70-2 ]
Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4861,4863
  • 83
  • [ 77-55-4 ]
  • 2-hydroxy-1,2-bis-(1-phenyl-cyclopentyl)-ethanone [ No CAS ]
Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4861,4863
  • 84
  • [ 77-55-4 ]
  • [ 68580-51-8 ]
Reference： [1]Chemische Berichte,1973,vol. 106,p. 2890 - 2903
  • 85
  • [ 77-55-4 ]
  • [ 17380-74-4 ]
YieldReaction ConditionsOperation in experiment
61% To a solution of carboxylic acid (1.5 g, 7.89 mmol) in H20/acetone (1: 10/12 mL total) at 0C was added Et3N (1.43 mL, 10.3 mmol) followed by addition of ethyl chloroformate (0.83 mL, 8.68 mmol). The resulting mixture was stirred for 30 min after which a solution of NaN3 (0.77g, 11. 8 mmol) in H20 (2 mL) was added dropwise. The resultant heterogenous mixture was stirred for 1 h at 0C, then cold water (5 mL) and Et20 (10 mL) were added. The layers were separated and the aqueous layer was extracted with Et20 (2 x 10 mL). The organic layers were combined, toluene (20 mL) was added, and the organic layers were dried (MgS04) and concentrated under reduced pressure to a volume of 20 mL. t-BuOH (5 mL) was added and the mixture was refluxed for 12h. The mixture was concentrated under reduced pressure and the crude residue was taken up in 3M HCI (30 mL) and was heated at reflux for 12h. The mixture was cooled to room temperature and extracted with Et20 (3 x 15 mL). The aqueous layer wa s cooled to 0 C and solid NaOH pellets were added until pH-12 was reached. The aqueous layer was extracted with Et20 (3 x 30 mL) and the combined organic layers were dried (MgS04) and concentrated under reduced pressure to afford 0.78 g (61 % yield) of an oil [MH+ 162]. This material was used without further purification.
Reference： [1]Patent: WO2005/68460,2005,A1 .Location in patent: Page/Page column 243
[2]Chemische Berichte,1973,vol. 106,p. 2890 - 2903
  • 86
  • [ 77-55-4 ]
  • 1,1'-Diphenylazocyclopentan [ No CAS ]
Reference： [1]Chemische Berichte,1973,vol. 106,p. 2890 - 2903
  • 87
  • [ 140-29-4 ]
  • n-butyl halide [ No CAS ]
  • [ 77-55-4 ]
Reference： [1]Chemische Berichte,1973,vol. 106,p. 2890 - 2903
[2]Helvetica Chimica Acta,1971,vol. 54,p. 868 - 897
  • 88
  • [ 77-55-4 ]
  • [ 726188-52-9 ]
  • C30H40IN3O [ No CAS ]
Reference： [1]Patent: US6391865,2002,B1 .Location in patent: Page column 83
  • 89
  • [ 77-55-4 ]
  • [ 457077-86-0 ]
YieldReaction ConditionsOperation in experiment
To a solution of carboxylic acid (1. 5 g, 7.89 MMOL) in H20/acetone (1: 10/12 mL total) at 0C was added Et3N (1.43 mL, 10.3 mmol) followed by addition of ethyl chloroformate (0.83 mL, 8.68 MMOL). The resulting mixture was stirred for 30 min after which a solution of NaN3 (0.77g, 11.8 MMOL) in H20 (2 mL) was added dropwise. The resultant heterogenous mixture was stirred for 1 h at 0C, then cold water (5 mL) and ET20 (10 mL) were added. The layers were separated and the aqueous layer was extracted with ET20 (2 x 10 mL). The organic layers were combined, toluene (20 mL) was added, and the organic layers were dried (MGS04) and concentrated under reduced pressure to a volume of 20 mL. T-BUOH (5 mL) was added and the mixture was REFLUXED for 12h. The mixture was concentrated under reduced pressure and the crude residue was taken up in 3M HCI (30 mL) and was heated at reflux for 12H. The mixture was cooled to room temperature and extracted with ET20 (3 x 15 mL). The aqueous layer was cooled to 0 C and solid NAOH pellets were added until PH-12 was reached. The aqueous layer was extracted with Et20 (3 x 30 mL) and the combined organic layers were dried (MGS04) and concentrated under reduced pressure to afford 0.78 g (61 % YIELD) of an oil [MH+ 162]. This material was used without further purification.
Reference： [1]Patent: WO2004/33440,2004,A1 .Location in patent: Page 280
  • 90
  • [ 77-55-4 ]
  • [ 135569-28-7 ]
YieldReaction ConditionsOperation in experiment
89% With sodium iodate; sulfuric acid; iodine; at 20 - 70℃; for 72h; Part A.1-Phenyl-cyclopentylcarboxylic acid (3.0 g, 15.8 mmol) was stirred inHOAc (10 mL) at RT underN2. I2 (4.01 g, 15.8 mmol) was added followed by the addition ofNaIO3 (0.78 g, 3.94 mmol) and conc. H2SO4 (0.3 mL). The resulting mixture was stirred at70 C for 3 days. The cooled mixture was poured intoH20, and extracted with EtOAc. The organic layer was washed with sodium thiosulfate and brine, dried overMgSO4, filtered, and concentrated to dryness to yield 4-iodophenylcylcopentylcarboxylic acid (4.45 g, yield:89%). LC/MS (ESI+) 317.6 (M+H) +.
Reference： [1]Patent: WO2003/99276,2003,A1 .Location in patent: Page 310
  • 91
  • [ 77-55-4 ]
  • [ 541-41-3 ]
  • [ 457077-86-0 ]
YieldReaction ConditionsOperation in experiment
To a solution of carboxylic acid (1.5 g, 7.89 mmol) in H2O/acetone (1:10/12 mL total) at 0 C. was added Et3N (1.43 mL, 10.3 mmol) followed by addition of ethyl chlo-roformate (0.83 mL, 8.68 mmol). The resulting mixture was stirred for 30 min after which a solution of NaN3 (0.77 g, 11.8 mmol) in H2O (2 mL) was added dropwise. The resultant heterogenous mixture was stirred for 1 h at 0 C., then cold water (5 mL) and Et2O (10 mL) were added. The layers were separated and the aqueous layer was extracted with Et2O (2x10 mL). The organic layers were combined, toluene (20 mL) was added, and the organic layers were dried (MgSO4) and concentrated under reduced pressure to a volume of 20 mL. t-BuOH (5 mL) was added and the mixture was re fluxed for 12 h. The mixture was concentrated under reduced pressure and the crude residue was taken up in 3M HC1 (30 mL) and was heated at reflux for 12 h. The mixture was cooled to room temperature and extracted with Et2O (3x15 mL). The aqueous layer was cooled to 0 C. and solid NaOH pellets were added until pH~12 was reached. The aqueous layer was extracted with Et2O (3x30 mL) and the combined organic layers were dried (MgSO4) and concentrated under reduced pressure to afford 0.78 g (61% yield) of an oil [MH+ 162]. This material was used without further purification.
Reference： [1]Patent: US2004/147559,2004,A1 .Location in patent: Page 152
  • 92
  • [ 77-55-4 ]
  • [ 1487-43-0 ]
  • [ 17380-74-4 ]
YieldReaction ConditionsOperation in experiment
61% To a solution of carboxylic acid (1.5 g, 7.89 mmol) in H2O/acetone (1:10/12 mL total) at 0 C. was added Et3N (1.43 mL, 10.3 mmol) followed by addition of ethyl chloroformate (0.83 mL, 8.68 mmol). The resulting mixture was stirred for 30 min after i 5 which a solution of NaN3 (0.77 g, 11.8 mmol) in H2O (2 mL) was added dropwise. The resultant heterogenous mixture was stirred for 1 h at 0 C., then cold water (5 mL) and Et2O (10 mL) were added. The layers were separated and the aqueous layer was extracted with Et2O (2?10 mL). The organic layers were combined, toluene (20 mL) was added, and the organic layers were dried (MgSO4) and concentrated under reduced pressure to a volume of 20 mL. t-BuOH (5 mL) was added and the mixture was refluxed for 12 h. The mixture was concentrated under reduced pressure and the crude residue was taken up in 3M HCl (30 mL) and was heated at reflux for 12 h. The mixture was cooled to room temperature and extracted with Et2O (3?15 mL). The aqueous layer was cooled to 0 C. and solid NaOH pellets were added until pH?12 was reached. The aqueous layer was extracted with Et2O (3?30 mL) and the combined organic layers were dried (MgSO4) and concentrated under reduced pressure to afford 0.78 g (61% yield) of an oil [MH+162]. This material was used without further purification.
Reference： [1]Patent: US2004/106794,2004,A1 .Location in patent: Page 152
  • 93
  • [ 77-55-4 ]
  • (R)-1-(4-chlorophenyl)-N-[1-[(hydroxyamino)carbonyl]-2-methylpropyl]-N-methylcyclopentanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% (12a) In a procedure analogous to that described for reaction (1c), 1-phenyl-1-cyclopentane carboxylic acid (144 mg, 0.755 mmol) was reacted with the amine (309 mg, 1.5 eq) from reaction (5S) at 60 C. for 60 h. Silica gel column chromatography (ethyl acetate-hexane, 15:85 then 25:75) yielded the desired product (78.4 mg, 25%). MS found: (M-H)-=407.
Reference： [1]Patent: US6376665,2002,B1
  • 94
  • [ 861359-74-2 ]
  • [ 77-55-4 ]
  • [ 17193-40-7 ]
  • [ 220880-33-1 ]
  • [ 220876-23-3 ]
YieldReaction ConditionsOperation in experiment
With stannous chloride; sodium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In ethanol; ethyl acetate; N,N-dimethyl-formamide; Example 26 Synthesis of N-[(1-Phenylcyclopentyl)carbonyl]-4-amino-L-phenylalanine Methyl Ester To a solution of 4-nitrophenylalanine hydrochloride methyl ester (3.90 g, 15 mmol) and 1-phenylcyclopentane carboxylic acid (3.4 g, 18 mmol) in 30 mL of DMF was added HBTU (6.8 g, 18 mmol) and diisopropylethyl amine (6.4 mL, 30 mmol) at room temperature. The mixture was then stirred at this temperature for 8 hr. The reaction was then diluted with 250 mL of ethyl acetate and was washed with 0.5 N HCl (40 mL), saturated NaHCO3 (2*40 mL) and saturated brine (2*40 mL). After removal of the solvent, the residue was purified on a silica gel column eluding with ethyl acetate:hexane (1:3) to give N-[(1-phenylcyclopentyl)carbonyl]-4-nitro-L-phenylalanine methyl ester (4.5 g, 75.7%). A suspension of N-[(1-phenylcyclopentyl)carbonyl]-4-nitro-L-phenylalanine methyl ester (3.5 g, 8.88 mmol) and stannous chloride (10 g, 44 mmol) in 60 mL of ethanol was refluxed for 50 min under argon. The ethanol was then removed under reduced pressure and the residue was treated with 50 mL of saturated NaHCO3 followed by sodium carbonate to adjust pH above 9. The white slurry was extracted with ethyl acetate (3*300 mL). The combined extracts were washed with water (100 mL) and brine (100 mL) and were dried (MgSO4). Removal of the solvent afforded 4-amino-N-[(1-phenylcyclopentyl)carbonyl]-L-phenylalanine methyl ester (2.9 g, 89%).
Reference： [1]Patent: US6455550,2002,B1
  • 95
  • [ 77-55-4 ]
  • [ 4535-96-0 ]
YieldReaction ConditionsOperation in experiment
1.89 g (88%) With hydrogenchloride; In methanol; dichloromethane; Step A Methyl-1-phenyl-1-cyclopentanecarboxylate A solution of <strong>[77-55-4]1-<strong>[77-55-4]phenyl-1-cyclopentanecarboxylic acid</strong></strong> (2.00 g, 10.51 mmol) in 30 mL methanol saturated with HCl was stirred at reflux for two hours. The reaction mixture was allowed to cool and the solvent was evaporated. The residue was dissolved in 50 mL dichloromethane and washed with 2N sodium hydroxide (3*25 mL). The organic layer was washed with water (2*25 mL) and dried (Na2 SO4). Evaporation of the solvent gave 1.89 g (88%) of methyl-1-phenyl-1-cyclopentanecarboxylate as a pale yellow liquid and was used in the next step without further purification. CIMS 205 m/z (M+1).
Reference： [1]Patent: US5331010,1994,A
  • 96
  • [ 77-55-4 ]
  • [ 6148-64-7 ]
  • [ 530-62-1 ]
  • [ 154382-30-6 ]
YieldReaction ConditionsOperation in experiment
With magnesium chloride; triethylamine; Step A: Preparation of beta-oxo-1-phenylcyclopentanepropanoic acid ethyl ester The title compound was prepared from <strong>[77-55-4]1-<strong>[77-55-4]phenyl-1-cyclopentanecarboxylic acid</strong></strong> (50.0 g, 0.220 mol), 1,1'-carbonyldiimidazole (43.0 g, 0.265 mol), magnesium chloride (40.0 g, 0.418 mol), ethyl potassium malonate (60.0 g, 0.352 mol), and triethylamine (48.9 g, 0.484 mol) using the procedure described in Example 3, Step A. Analysis for C16 H20 O3: Calcd: C, 73.81; H, 7.74; Found: C, 74.04; H, 7.46.
Reference： [1]Patent: US5278326,1994,A
YieldReaction ConditionsOperation in experiment
EXAMPLE 25 Synthesis of sulfamic acid(cyclopentylphenylacetyl)-2,6-bis(1-methylethyl)phenyl ester This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with alpha-phenylcyclopentanecarboxylic acid, mp 142-143 C.
YieldReaction ConditionsOperation in experiment
EXAMPLE 30 Synthesis of sulfamic acid[(1-phenylcyclopentyl)carbonyl]-2,6-bis(1-methylethyl)phenyl ester This compound was prepared in the same manner as for the title compound of Example 1, except that 2,6-diisopropylphenylacetic acid was replaced with 1-phenyl-1-cyclopentanecarboxylic acid, mp 149-152 C.
  • 99
  • [ 77-55-4 ]
  • [ 168163-99-3 ]
  • [ 168162-96-7 ]
YieldReaction ConditionsOperation in experiment
(Example 52) Using 280 mg of 1-phenylcyclopentylcarboxylic acid and 500 mg of methyl (Z)-[1-(4-aminobenzoyl)-4,4-difluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetate, a similar procedure as in Reference Example 8 was repeated to obtain 533 mg of methyl (Z)-[4,4-difluoro-1-[4-(1-phenylcyclopentylcarbonyl)amino]benzoyl-2,3,4,5-tetrahydro-1H-1-benzazepin-5-ylidene]acetate. 1 H-NMR (deltappm in CDCl3, TMS internal standard): 1.71 (2H, m), 1.85 (2H, m), 2.07 (2H, m), 2.20-2.80 (total 4H), 3.21 (1H, m), 3.81 (3H, s), 5.03 (1H, m), 6.13 (1H, s), 6.67 (1H, d), 6.78 (1H, s), 7.05 (2H, d), 7.09 (1H, t), 7.14 (2H, d), 7.22 (1H, t), 7.26-7.41 (total 6H) MS (FAB): 545 (M+ +1).
Reference： [1]Patent: US5710150,1998,A
  • 100
  • [ 77-55-4 ]
  • [ 94790-37-1 ]
  • [ 217172-23-1 ]
  • [ 256653-09-5 ]
YieldReaction ConditionsOperation in experiment
45% In diethyl ether; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; Step C 1-Phenyl-1-cyclopentanecarboxylic acid (0.171 g, 0.899 mmol) was dissolved in dry DMF (3 mL) under a nitrogen atmosphere and cooled to 0 C. in an ice-water bath. To this solution were added in succession N,N-diisopropylethylamine (0.310 mL, 1.80 mmol) and solid O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (0.341 g, 0.899 mmol, Novabiochem, La Jolla, Calif.). The resulting reaction mixture was stirred at 0 C. for 30 minutes, (S)-2-Amino-3-(4-benzyloxy-phenyl)-N-tert-butyl-propionamide (0.293 g, 0.899 mmol) was then added. After an additional 60 minutes stirring at 0 C. the reaction mixture was mixed with 60 mL of diethyl ether. The resulting mixture was successively washed with 5% aqueous HCl solution, brine, saturated aqueous NaHCO3 solution and brine, and was dried over Na2SO4. The solution was concentrated in vacuo, and an oil was obtained. The crude residue was purified by chromatography (silica gel, 60% ether in hexanes) to give the title compound as a white foam (0.20 g, 45%); mp 40-50 C. APCI-MS: m/z 499.6 (MH+).
Reference： [1]Patent: US6180677,2001,B2
  • 101
  • cis-N-(3-phenylpropyl)-6-amino-4a-(3-methoxyphenyl)-8a-methyloctahydroisoquinoline [ No CAS ]
  • [ 77-55-4 ]
  • 1-phenylcyclopentanecarboxylic acid cis-[4a-(3-methoxyphenyl)-8a-methyl-2-(3-phenylpropyl)octahydroisoquinolin-6-yl]amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; at 20℃; for 2h; 1-Phenylcyclopentanecarboxylic Acid [4a-(3-Methoxyphenyl)-8a-methyl-2-(3-phenylpropyl)octahydroisoquinolin-6-yl]amide (25c); To compound 24 (71 mg, 0.180 mmol) dissolved in anhydrous THF (15 mL) was added <strong>[77-55-4]1-<strong>[77-55-4]phenyl-1-cyclopentanecarboxylic acid</strong></strong> (51 mg, 0.27 mmol), triethylamine (0.126 mL, 0.904 mmol), and BOP reagent (88 mg, 0.20 mmol), and the reaction mixture was allowed to stir at room temperature for 2 h. Reaction progress was monitored by TLC (30% CMA 80 in CH2Cl2). The reaction mixture was diluted with EtOAc (25 mL) and washed with saturated aqueous NaHCO3 (25 mL) followed by water (25 mL). The aqueous layers were back extracted with EtOAc (2×20 mL). The combined organic layers were washed with 1 N NaOH (30 mL), dried (MgSO4), and concentrated under reduced pressure to afford crude product. The crude product was purified by flash chromatography (25% CMA 80 in CH2Cl2) to afford 94 mg (92%): LCMS (ESI): m/z 565.6 (M+H)+; 1H NMR (CDCl3, 300 MHz) delta 7.17-7.36 [m, 13H], 6.71-6.73 [m, 1H], 4.92, [d, J=6 Hz, 1H], 4.19 [m, 1H], 3.79 [s, 3H], 2.74 [br, 1H], 2.62-2.64 [m, 2H], 2.33-2.45 [m, 5H], 2.10-2.31 [m, 2H], 1.98-2.09 [m, 3H], 1.61-1.84 [m, 10H], 1.46 [d, J=12 Hz, 1H], 1.20-1.33 [m, 2H], 1.15 [s, 3H]; 13C NMR (CDCl3, 300 MHz) delta 176.1, 159.2, 148.9, 144.8, 142.8, 129.0, 128.9, 128.7, 128.6, 127.2, 127.1, 126.0, 121.9, 116.3, 110.7, 62.2, 59.6, 58.2, 55.5, 51.2, 46.2, 44.2, 37.8, 37.4, 37.2, 36.9, 36.6, 35.6, 33.9, 29.2, 28.1, 26.6, 24.4.
Reference： [1]Patent: US2007/27182,2007,A1 .Location in patent: Page/Page column 15
  • 102
  • [ 106-52-5 ]
  • [ 77-55-4 ]
  • [ 3613-68-1 ]
YieldReaction ConditionsOperation in experiment
Comparative Example 1; l,l-Dimethyl-4-[(l-phenylcyclopentyl)carbonyl]oxy}piperidinium iodide; Comparative Example IA: l-Methylpiperidin-4-yl 1-phenylcyclopentanecarboxylate; To a stirred solution of 1-phenylcyclopentane carboxylic acid (0.38 g) in dichloromethane (5 mL) was added oxalyl chloride (0.52 mL) and DMF (one drop) at RT. After 2 h, gas evolution had ceased, and the mixture was concentrated in vacuo and redissolved in dichloromethane. JV-Methyl 4-hydroxy piperidine (0.3 g) and triethylamine (0.42 mL) were added, and the mixture was warmed overnight at 40C. The mixture was partitioned between dichloromethane and water, washed with water, and the organic phase dried over sodium sulfate, filtered and concentrated in vacuo. The residue was subjected to flash <n="55"/>column chromatography, eluting with dichloromethane then 1% and 2% methanol/dichloromethane to leave a white solid (0.385 g).m/z 288 [M+H]+5 1H NMR (399.822 MHz, CDCl3) delta 7.37 (dm, 2H), 7.29 (tm, 2H), 7.21 (tm, IH), 4.77 - 4.69 (m, IH), 2.71 - 2.64 (m, 2H), 2.39 - 2.29 (m, 2H), 2.26 - 2.22 (m, 2H), 2.21 (s, 3H), 1.95 - 1.85 (m, 2H), 1.81 - 1.67 (m, 6H), 1.64 - 1.54 (m, 2H).
Reference： [1]Patent: WO2008/59239,2008,A1 .Location in patent: Page/Page column 53-54
  • 103
  • 4-hydroxymethylphenoxymethyl polystyrene resin [ No CAS ]
  • [ 77-55-4 ]
  • C19H20NO3Pol [ No CAS ]
Reference： [1]Tetrahedron,2009,vol. 65,p. 638 - 643
  • 104
  • [ 77-55-4 ]
  • [ 201230-82-2 ]
  • [ 41058-64-4 ]
Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14082 - 14083
  • 105
  • [ 77-55-4 ]
  • potassium phenyltrifluoborate [ No CAS ]
  • C18H18O2 [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 17676 - 17677
  • 106
  • [ 77-55-4 ]
  • 1-phenyl-cyclopentyl isocyanate [ No CAS ]
Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 385 - 386
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 15436 - 15440
    Angew. Chem.,2017,vol. 129,p. 15638 - 15642,5
[3]Organic Letters,2018,vol. 20,p. 6530 - 6533
  • 107
  • [ 77-55-4 ]
  • (3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine [ No CAS ]
  • N-[(3aS*,4R*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-1-phenylcyclopentanecarboxamide [ No CAS ]
  • N-[(3aS*,4S*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-1-phenylcyclopentanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20℃; 1-Hydroxybenzotriazole (33 mg, 0.24 mmol) and N-(3-dimethylaminopropyl)-N-ethylcarbodiimide (43 muL, 0.24 mmol) were added to a solution of <strong>[77-55-4]1-phenylcyclopentanecarboxylic acid</strong> (46 mg, 0.24 mmol) in dichloromethane (2 mL). The reaction was stirred at room temperature for 10 minutes, then (3aS*,6aR*)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine (52 mg, 0.24 mmol) was added and the reaction stirred at room temperature overnight. The reaction was quenched with water, and extracted with dichloromethane, then purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/chloroform as eluent to give the title compounds.Example 11H NMR (500 MHz, pyridine-d5) delta ppm 7.52-7.28 (m, 9H), 7.25 (d, J=7.7, 1H), 4.43-4.34 (m, 1H), 3.56 (d, J=12.9, 1H), 3.17 (d, J=12.9, 1H), 2.83-2.67 (m, 2H), 2.59-2.50 (m, 1H), 2.50-2.44 (m, 1H), 2.35-2.29 (m, 2H), 2.04-1.87 (m, 4H), 1.84-1.54 (m, 6H), 1.43-1.26 (m, 1H), 1.04-0.94 (m, 1H); MS (ESI+) m/z 389 (M+H)+.Example 21H NMR (500 MHz, pyridine-d5) delta ppm 7.52-7.47 (m, 2H), 7.41 (d, J=7.4, 2H), 7.38-7.29 (m, 4H), 7.25 (q, J=7.3, 2H), 4.36 (m, 1H), 3.57 (d, J=13.2, 1H), 3.40 (d, J=13.2, 1H), 2.78 (m, 3H), 2.33 (m, 3H), 2.27 (d, J=8.7, 1H), 2.21-2.13 (m, 1H), 1.99 (dt, J=5.8, 11.7, 3H), 1.87-1.75 (m, 2H), 1.71-1.60 (m, 3H), 1.44 (ddd, J=7.7, 12.1, 14.5, 1H), 1.31 (m, 1H); MS (ESI+) m/z 389 (M+H)+.
Reference： [1]Patent: US2010/130558,2010,A1 .Location in patent: Page/Page column 41
  • 108
  • [ 77-55-4 ]
  • [ 38330-80-2 ]
  • [ 880352-58-9 ]
YieldReaction ConditionsOperation in experiment
65% To a 500 mL round bottom flask containing phenylcyclopentane carboxylic acid 1 (14 g, 73 mmol) was added anhydrous THF (200 mL). Carbonyldiimidazole (12.5 g, 77 mmol) was added to the reaction mixture, which was then allowed to stir for 2 hr. at room temperature. A mixture of magnesium chloride (7.7 g, 81 mmol) and potassium monomethylmalonate (12.6 g, 81 mmol) was added, and the solution was heated to 50° C. and stirred overnight. The solid was filtered off and washed with THF. The filtrate was evaporated then dissolved in ethyl acetate. The mixture was washed with 1N HCl (1.x.) and 5percent aqueous sodium bicarbonate (2.x.). The combined organic layers were then dried over anhydrous magnesium sulfate, filtered, and concentrated to give a waxy pale yellow solid (11.7 g, 65percent yield) which was used without further purification. 1H NMR (CDCl3, 400 MHz): delta=7.34 (m, 2H), 7.27 (m, 3H), 3.63 (s, 3H), 3.28 (s, 2H), 2.53-2.47 (m, 2H), 1.98-1.90 (m, 2H), 1.72 (m, 4H).
Reference： [1]Patent: US2006/63790,2006,A1 .Location in patent: Page/Page column 3; 8

Tags: 77-55-4 synthesis path| 77-55-4 SDS| 77-55-4 COA| 77-55-4 purity| 77-55-4 application| 77-55-4 NMR| 77-55-4 COA| 77-55-4 structure

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Technical Information

• Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Amide Hydrolysis • Amide Hydrolysis • Anhydride Hydrolysis • Arndt-Eistert Homologation • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Decarboxylation of Substituted Propanedioic • Deprotection of Cbz-Amino Acids • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Esters Hydrolyze to Carboxylic Acids and Alcohols • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation • Halogenation of Benzene • Heat of Combustion • Hunsdiecker-Borodin Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Nitration of Benzene • Nitriles Hydrolyze to Carboxylic Acids • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Sulfonation of Benzene • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Conversion of Carboxylic Acids into Acyl Halides • The Nitro Group Conver to the Amino Function • Ugi Reaction • Vilsmeier-Haack Reaction
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