Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
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 : |
|
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 |
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 |
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 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
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 |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.17 |
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: |
* 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.
Yield | Reaction Conditions | Operation 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)+. |
Yield | Reaction Conditions | Operation 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+). |
Yield | Reaction Conditions | Operation 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. |
[ 37828-19-6 ]
1-Phenylcyclobutanecarboxylic acid
Similarity: 0.95
[ 1135-67-7 ]
1-Phenylcyclohexanecarboxylic acid
Similarity: 0.95
[ 80789-75-9 ]
1-(p-Tolyl)cyclopentanecarboxylic acid
Similarity: 0.95
[ 13491-13-9 ]
(R)-3-Methyl-2-phenylbutanoic acid
Similarity: 0.94
[ 37828-19-6 ]
1-Phenylcyclobutanecarboxylic acid
Similarity: 0.95
[ 1135-67-7 ]
1-Phenylcyclohexanecarboxylic acid
Similarity: 0.95
[ 80789-75-9 ]
1-(p-Tolyl)cyclopentanecarboxylic acid
Similarity: 0.95
[ 13491-13-9 ]
(R)-3-Methyl-2-phenylbutanoic acid
Similarity: 0.94