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[ CAS No. 6120-95-2 ] {[proInfo.proName]}

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Chemical Structure| 6120-95-2
Chemical Structure| 6120-95-2
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Product Details of [ 6120-95-2 ]

CAS No. :6120-95-2 MDL No. :MFCD00001288
Formula : C10H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IWWCCNVRNHTGLV-UHFFFAOYSA-N
M.W : 162.19 Pubchem ID :80206
Synonyms :

Calculated chemistry of [ 6120-95-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.37
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) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.62
Log Po/w (XLOGP3) : 1.73
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 2.25
Consensus Log Po/w : 1.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.17
Solubility : 1.09 mg/ml ; 0.00671 mol/l
Class : Soluble
Log S (Ali) : -2.13
Solubility : 1.2 mg/ml ; 0.00742 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.428 mg/ml ; 0.00264 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.17

Safety of [ 6120-95-2 ]

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

Application In Synthesis of [ 6120-95-2 ]

* 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.

  • Upstream synthesis route of [ 6120-95-2 ]
  • Downstream synthetic route of [ 6120-95-2 ]

[ 6120-95-2 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 935-44-4 ]
  • [ 6120-95-2 ]
YieldReaction ConditionsOperation in experiment
50% at 110℃; Reflux Step (vi): Synthesis of 1-phenylcyclopropanecarboxylic acidExperimental procedure: To a solution of 1-phenylcyclopropanecarbonitrile (7 g, mmoles) was added water (15 mL), acetic acid (15 mL) and sulfuric acid (15 mL). The contents were then refluxed at 110 °C over night. The reaction mixture was extracted with ethyl acetate and the organic layer was washed with brine solution (2 x 50 mL), dried over Na2S04 and concentrated under reduced pressure to give the crude product. The crude was purified by flash column chromatography over silica gel (230-400 mesh) and elution with 5percent ethyl acetate in hexane, gave the desired product as a colorless solid (4.35 g, 50percent).
12 g With water; potassium hydroxide In ethanol at 100℃; for 16 h; Potassium hydroxide solution in water (50percent, 100 mL) was added into a solution of 1- phenylcyclopropanecarbonitrile (20 g) in ethanol (100 mL) at room temperature. The reaction mixture was stirred at 100°C for 16 hours before being cooled to room temperature. The reaction mixture was concentrated to remove ethanol and the aqueous layer was washed with dichloromethane (2 x 200 mL). The aqueous layer was slowly neutralized with concentrated HCl and pH was adjusted to 3-4. The solid obtained was filtered, washed with water (3 x 50 mL) and dried under vacuum to get desired 1- phenylcyclopropanecarboxylic acid (12 g) as white solid. ^- MR (CDC13): δ 1.26-1.30 (m, 2H), 1.59-1.66 (m, 2H), 7.20-7.30 (m, 5H), 8.6 (s, 1H). MS: 163 (M + H)+.
Reference: [1] Pharmaceutical Chemistry Journal, 1980, vol. 14, # 2, p. 114 - 118[2] Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 2, p. 40 - 45
[3] European Journal of Medicinal Chemistry, 1991, vol. 26, # 2, p. 125 - 128
[4] Patent: WO2012/12410, 2012, A2, . Location in patent: Page/Page column 46-47
[5] Journal of Organic Chemistry, 1959, vol. 24, p. 616,618, 619
[6] Helvetica Chimica Acta, 1971, vol. 54, p. 868 - 897
[7] Chemische Berichte, 1973, vol. 106, p. 2890 - 2903
[8] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1775 - 1779[9] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 10, p. 2086 - 2091
[10] Patent: US2012/172349, 2012, A1, . Location in patent: Page/Page column 24
[11] Patent: WO2014/160689, 2014, A1, . Location in patent: Page/Page column 59-60
[12] Patent: US9404081, 2016, B2, . Location in patent: Page/Page column 98
[13] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6545 - 6549
[14] Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311
  • 2
  • [ 31729-66-5 ]
  • [ 6120-95-2 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 7, p. 2564 - 2566
[2] Organic Syntheses, 2005, vol. 81, p. 195 - 203
[3] Tetrahedron Letters, 1998, vol. 39, # 30, p. 5323 - 5326
  • 3
  • [ 103-82-2 ]
  • [ 106-93-4 ]
  • [ 6120-95-2 ]
Reference: [1] Tetrahedron Letters, 2005, vol. 46, # 4, p. 635 - 638
  • 4
  • [ 87328-17-4 ]
  • [ 6120-95-2 ]
Reference: [1] Chemische Berichte, 1986, vol. 119, # 12, p. 3694 - 3703
  • 5
  • [ 6120-96-3 ]
  • [ 6120-95-2 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, # 10, p. 1775 - 1779[2] Zhurnal Organicheskoi Khimii, 1980, vol. 16, # 10, p. 2086 - 2091
  • 6
  • [ 140-29-4 ]
  • [ 6120-95-2 ]
Reference: [1] Patent: WO2012/12410, 2012, A2,
[2] Patent: US2012/172349, 2012, A1,
[3] Patent: WO2014/160689, 2014, A1,
[4] Patent: US9404081, 2016, B2,
[5] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6545 - 6549
[6] Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311
  • 7
  • [ 52370-86-2 ]
  • [ 6120-95-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1991, vol. 26, # 2, p. 125 - 128
  • 8
  • [ 4553-07-5 ]
  • [ 6120-95-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 1991, vol. 26, # 2, p. 125 - 128
  • 9
  • [ 65655-78-9 ]
  • [ 6120-95-2 ]
Reference: [1] Chemische Berichte, 1986, vol. 119, # 12, p. 3694 - 3703
  • 10
  • [ 22286-82-4 ]
  • [ 6120-95-2 ]
Reference: [1] Chemische Berichte, 1986, vol. 119, # 12, p. 3694 - 3703
  • 11
  • [ 103-79-7 ]
  • [ 6120-95-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1964, p. 1993 - 2000
  • 12
  • [ 1007-71-2 ]
  • [ 6120-95-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1964, p. 1993 - 2000
  • 13
  • [ 6120-95-2 ]
  • [ 422280-53-3 ]
  • [ 23348-99-4 ]
Reference: [1] Patent: US2004/6056, 2004, A1, . Location in patent: Page 39
  • 14
  • [ 6120-95-2 ]
  • [ 23348-99-4 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 12, p. 3814 - 3820
[2] Patent: WO2003/99276, 2003, A1, . Location in patent: Page 236-237
  • 15
  • [ 6120-95-2 ]
  • [ 73930-39-9 ]
YieldReaction ConditionsOperation in experiment
71% With sodium azide; sulfuric acid In chloroform 1-Phenylcyclopropa ne carboxylic acid(1) is reacted with sodium azide and sulfuric acid in CHCl3 to yield 1-phenylcyclopropanamine (2). 1-Phenylcyclopropanamine is then reacted with 2-mesitylenesulfonyl chloride in chloroform under basic conditions to yield the protected derivative (3), N-(I- phenylcyclopropyl)mesitylenesulfonamide. N-(I- phenylcyclopropyl)mesitylenesulfonamide (3) is then reacted with N-(4- bromobutyl)phthalimide (4) in DMF with sodium hydride at room temperature overnight, to yield N-(2-mesitylenesulfonyl)-N-(l-phenylcyclopropyl)-4- phthalimidobutylamine (5).[0092] The phthaloyl group is removed from N-(2-mesitylenesulfonyi)-N-(l- phenylcyclopropyl)-4-phthalimidobutylamine (5) by reaction with hydroxylamine hydrochloride in benzene and sodium methoxide in methanol, to produce N-(4- aminobutyl)-N-(l-phenylcyclopropyl)-2-mesitylenesulfonamide (6). The free amino group is then re-protected with 2-mesitylenesulfonyl chloride in 2N NaOH in CHCl3 to give (7), N-(4-(mesitylene-2-sulfonylamino)butyl)-N-(l-phenylcyclopropyl)~2- mesitylenesulfonamide. (7) is then reacted with l,2-bis(mesitylene-2- --> sulfonyloxymethyl)cyclopropane (8) in DMF with sodium hydride at room temperature overnight to yield (9), the tetra-mesitylene-2-sulfonyl- protected derivative of l,2-bis((N-(l-phenylcyclopropyl)-4- aminobutyl)aminomethyl)cyclopropane. The mesitylene protecting groups are then removed using HBr in acetic acid and phenol in methylene chloride to yield 1,2- bis((N-(l-phenylcyclopropyl)-4-aminobutyl)aminomethyl)cyclopropane (CGC-11255; SL-11255).
51%
Stage #1: With diphenyl phosphoryl azide; triethylamine In toluene for 0.75 h; Reflux
Stage #2: With ammonium chloride In water; toluene
INTERMEDIATE PREPARATION 31 -phenylcyclop hydrochloride.bul.HCITo a solution of 1-phenylcyclopropanecarboxylic acid (8.80 g, 54.3 mmol) in toluene (260 mL) was added diphenylphosphoryl azide (12.12 mL, 56.2 mmol) and Et3N (8.94 mL, 64.1 mmol). The mixture was heated to reflux for 45 min, cooled to room temperature, and quenched with saturated aqueous NH4CI (860 mL). The two phases were separated and the aqueous phase extracted with Et20 (3 x 400 mL). The combined ethereal extracts were washed with brine, dried over MgS04, filtered and concentrated in vacuo to provide the isocyanate as oil. This material was dissolved in Et20 (40 ml.) and concentrated HCI (30 ml.) was added. The resulting mixture was heated on a steam bath for 30 min. Acetone (100 ml.) was added to the mixture and the precipitate was isolated by filtration to provide 1- phenylcyclopropanamine (4.68 g, 51 percent) as the hydrochloride salt. 1H NMR (400 MHz, DMSO-de) δ 9.01 (br. s., 3H), 7.37 - 7.48 (m, 4H), 7.30 - 7.37 (m, 1 H), 1 .38 - 1.46 (m, 2H), 1.14 - 1.21 (m, 2H); MS (m/z) 133.8 (M+H+).
Reference: [1] Patent: WO2006/86773, 2006, A2, . Location in patent: Page/Page column 32-34
[2] Patent: WO2011/119704, 2011, A1, . Location in patent: Page/Page column 35-36
[3] Synthetic Communications, 1980, vol. 10, # 2, p. 107 - 110
  • 16
  • [ 7647-01-0 ]
  • [ 6120-95-2 ]
  • [ 73930-39-9 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 5, p. 549 - 554
  • 17
  • [ 6120-95-2 ]
  • [ 139633-98-0 ]
Reference: [1] Patent: WO2012/83105, 2012, A1,
  • 18
  • [ 6120-95-2 ]
  • [ 345965-52-8 ]
YieldReaction ConditionsOperation in experiment
75.14% at 15 - 55℃; for 48.25 h; Sealed tube; Inert atmosphere A sealed tube was charged with 1-phenyl cyclopropane carboxylic acid (3.0 g, 18.5mmol), sodium acetate (1.75 g, 1.1 eq) and glacial acetic acid (10 mL). To the stirredsolution at 15 00, Br2 (1 .2 mL, 1 .0 eq) was added under nitrogen atmosphere. Then, the reaction mixture was stirred at room temperature for 15 mm and gradually raised the temperature to 55 00 and maintained the same for another 48 h. The reaction mixture was quenched with ice water and extracted with ethyl acetate. The organiclayer was washed with water and brine solution and then wasdried and concentrated. The obtained product was triturated with n-hexane to yield the title compound (3.34 g, 75.14percent) as a pale yellowish solid.
Reference: [1] Patent: WO2014/202580, 2014, A1, . Location in patent: Page/Page column 128
[2] Patent: US2008/81802, 2008, A1, . Location in patent: Page/Page column 8
  • 19
  • [ 6120-95-2 ]
  • [ 100-51-6 ]
  • [ 1324000-40-9 ]
Reference: [1] Synthesis, 2011, # 9, p. 1477 - 1483
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