Home Cart 0 Sign in  
X

[ CAS No. 52485-51-5 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 52485-51-5
Chemical Structure| 52485-51-5
Chemical Structure| 52485-51-5
Structure of 52485-51-5 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 52485-51-5 ]

Related Doc. of [ 52485-51-5 ]

Alternatived Products of [ 52485-51-5 ]

Product Details of [ 52485-51-5 ]

CAS No. :52485-51-5 MDL No. :MFCD11611631
Formula : C11H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OKDZNDUPIRUYLF-NSHDSACASA-N
M.W :193.24 Pubchem ID :11492087
Synonyms :

Calculated chemistry of [ 52485-51-5 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 54.8
TPSA : 49.33 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) : -6.85 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 0.88
Log Po/w (WLOGP) : 0.73
Log Po/w (MLOGP) : 1.29
Log Po/w (SILICOS-IT) : 1.66
Consensus Log Po/w : 1.22

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.58
Solubility : 5.09 mg/ml ; 0.0263 mol/l
Class : Very soluble
Log S (Ali) : -1.5
Solubility : 6.11 mg/ml ; 0.0316 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.164 mg/ml ; 0.000849 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.68

Safety of [ 52485-51-5 ]

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 [ 52485-51-5 ]

* 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 [ 52485-51-5 ]
  • Downstream synthetic route of [ 52485-51-5 ]

[ 52485-51-5 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 3182-95-4 ]
  • [ 108-24-7 ]
  • [ 52485-51-5 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 0.166667 h; Green chemistry In a 50mL round-bottomed flask, a mixtureof amine or amino alcohol (1 mmol) and aceticanhydride (1.2 mmol) was stirred at roomtemperature for the appropriate time. Aftercompletion of the reaction, as monitored by TLC,the reaction mixture was dissolved in ether (5 mL)and was allowed to stand at room temperature for1 hour. During this time, crystal of product formed,which were collected by filtration.In the case of solid substrates(sulfonamides), the same protocol was used.However, the use of water was required for thesolubility of the mixture. The N-acylatedsulfonamides were collected by crystallization fromdiethyl ether.
78% at -20℃; for 2 h; To a solution of l-phenylalaninol (1 g, 6.6 mmol) in pyridine (20 mL) at -20 °C, acetic anhydride (0.7 mL, 7.26 mmol) was added dropwise, and the solution was stirred at -20 °C for 2 h after which TLC (EtOAc/CH2Cl2/MeOH 6:2:2) (stained with ninhydrin) showed no starting material. The reaction was quenched with methanol (3 mL) then evaporated in vacuo. The residue was dissolved in EtOAc (15 mL), washed with water (2 x 15 mL), brine (2 x 15 mL), dried over anhydrous MgSO4 and filtered. The filtrate was evaporated to dryness to afford 11 as white needles which was recrystallized from EtOAc, (1.1 g, 78percent); mp 98-99 °C; 1H NMR (270 MHz, CDCl3): δ 7.25-7.21 (m, 5H, Ar), δ 5.7 (br s, 1H, NH), δ 4.15-4.12 (m, 1H, CH-NH), δ 3.66-3.58 (m, 2H, CH2-OH), δ 2.87-2.84 (d, 2H, CH2-Ph), δ 2.64-2.62 (t, 1H, OH), δ 2.03 (s, 3H, Ac); HRMS (ESI+): (Mwt. 193); m/z found: 194.1168 [M+H]+, C11H16NO2 requires 194.1181 and 216.0987 [M+Na]+, C11H15NO2Na requires 216.1000.
75% for 16 h; To a stirred solution of L-phenylalaninol (228 mg, 1.51 mmol) in THF (5 mL) was added acetic anhydride (0.15 mL, 1.59 mmol) and the mixture stirred for 16 h. The reaction mixture was diluted with EtOAc (10 mL) and washed with 1 N HCL (15 mL), saturated aqueous sodium bicarbonate (15 mL) and brine (15 mL). The organic phase was dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by column chromatography on silica gel afforded the N-acetylated alcohol (220 mg, 75percent) as a white solid. 1H NMR (CDCl3) δ 1.95 (s, 3H), 2.87 (d, 2H, J=6.0 Hz), 3.17 (br s, 1H), 3.56-3.68 (m, 2H), 4.13-4.21 (m, 1H), 5.97 (br d, 1H, J=6.0 Hz), 7.20-7.34 (m, 5H). The alcohol was then oxidized according to the general Dess-Martin procedure and the crude aldehyde used without further purification.
Reference: [1] Chinese Chemical Letters, 2010, vol. 21, # 2, p. 155 - 158
[2] Oriental Journal of Chemistry, 2015, vol. 31, # 2, p. 913 - 919
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 10, p. 2742 - 2755
[4] Patent: US6750348, 2004, B1, . Location in patent: Page column 47
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2216 - 2220
  • 2
  • [ 3618-96-0 ]
  • [ 52485-51-5 ]
YieldReaction ConditionsOperation in experiment
87% With lithium borohydride In tetrahydrofuran at 0℃; for 4 h; General procedure: To a solution of compound (S)-2 (19.9g, 90.0mmol) in THF (300mL) was added LiBH4 (2.97g, 135.0mmol) at 0°C and then the reaction mixture was stirred for 4h at this temperature. The reaction was quenched with aqueous NaOH. After filtration, the organic solvent was evaporated under reduced pressure to give the crude product. Purification by column chromatography (silica gel, CH2Cl2/CH3OH=50:1, v/v) afforded compound (S)-3 (15.1g, 87percent) as a white solid. Mp=92–94°C; [α]D20 −20.8 (c 1.20, CHCl3); 1H NMR (400MHz, DMSO-d6) δ 7.69 (d, J=8.0Hz, 1H), 7.26 (t, J=7.6Hz, 2H), 7.21–7.17 (m, 3H), 4.75 (br s, 1H), 3.92–3.83 (m, 1H), 3.36–3.28 (m,2H), 2.82 (dd, J=13.6, 5.6Hz, 1H), 2.59 (dd, J=13.6, 8.4Hz, 1H), 1.74 (s, 3H); 13C NMR (100MHz, DMSO-d6) δ 168.80, 139.30, 129.05 (2C), 128.07 (2C), 125.86, 62.58, 52.40, 36.62, 22.73; HRMS calcd for C11H16NO2 [M+H]+ 194.1176, found 194.1173.
Reference: [1] Chemical Communications, 2015, vol. 51, # 49, p. 9991 - 9994
[2] Tetrahedron, 2014, vol. 70, # 31, p. 4602 - 4610
  • 3
  • [ 132836-66-9 ]
  • [ 90719-32-7 ]
  • [ 52485-51-5 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 14, p. 2497 - 2499
  • 4
  • [ 3182-95-4 ]
  • [ 75-36-5 ]
  • [ 52485-51-5 ]
Reference: [1] Heterocycles, 1995, vol. 41, # 5, p. 947 - 958
  • 5
  • [ 7524-50-7 ]
  • [ 52485-51-5 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 31, p. 4602 - 4610
[2] Chemical Communications, 2015, vol. 51, # 49, p. 9991 - 9994
  • 6
  • [ 35593-55-6 ]
  • [ 52485-51-5 ]
Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 14, p. 1940 - 1951
  • 7
  • [ 63-91-2 ]
  • [ 52485-51-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2216 - 2220
  • 8
  • [ 108-22-5 ]
  • [ 3182-95-4 ]
  • [ 52485-51-5 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 8, p. 2251 - 2255
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 52485-51-5 ]

Aryls

Chemical Structure| 84773-29-5

[ 84773-29-5 ]

(S)-2-(Methylamino)-3-phenylpropan-1-ol

Similarity: 0.84

Chemical Structure| 149709-44-4

[ 149709-44-4 ]

(2R,4S)-5-([1,1'-Biphenyl]-4-yl)-4-(3-carboxypropanamido)-2-methylpentanoic acid

Similarity: 0.74

Chemical Structure| 132127-34-5

[ 132127-34-5 ]

(3R,4S)-3-Hydroxy-4-phenylazetidin-2-one

Similarity: 0.73

Chemical Structure| 1202-66-0

[ 1202-66-0 ]

N-(4-Hydroxyphenethyl)acetamide

Similarity: 0.72

Chemical Structure| 1260672-03-4

[ 1260672-03-4 ]

5-Phenylmorpholin-3-one

Similarity: 0.72

Alcohols

Chemical Structure| 84773-29-5

[ 84773-29-5 ]

(S)-2-(Methylamino)-3-phenylpropan-1-ol

Similarity: 0.84

Chemical Structure| 63006-93-9

[ 63006-93-9 ]

(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol

Similarity: 0.79

Chemical Structure| 62855-02-1

[ 62855-02-1 ]

(R)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol

Similarity: 0.79

Chemical Structure| 18881-17-9

[ 18881-17-9 ]

(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol

Similarity: 0.79

Chemical Structure| 132127-34-5

[ 132127-34-5 ]

(3R,4S)-3-Hydroxy-4-phenylazetidin-2-one

Similarity: 0.73

Amides

Chemical Structure| 149709-44-4

[ 149709-44-4 ]

(2R,4S)-5-([1,1'-Biphenyl]-4-yl)-4-(3-carboxypropanamido)-2-methylpentanoic acid

Similarity: 0.74

Chemical Structure| 132127-34-5

[ 132127-34-5 ]

(3R,4S)-3-Hydroxy-4-phenylazetidin-2-one

Similarity: 0.73

Chemical Structure| 1202-66-0

[ 1202-66-0 ]

N-(4-Hydroxyphenethyl)acetamide

Similarity: 0.72

Chemical Structure| 1260672-03-4

[ 1260672-03-4 ]

5-Phenylmorpholin-3-one

Similarity: 0.72

Chemical Structure| 1347675-92-6

[ 1347675-92-6 ]

(R)-N-(Tetrahydro-2H-pyran-3-yl)benzamide

Similarity: 0.71

Amines

Chemical Structure| 84773-29-5

[ 84773-29-5 ]

(S)-2-(Methylamino)-3-phenylpropan-1-ol

Similarity: 0.84

Chemical Structure| 149709-44-4

[ 149709-44-4 ]

(2R,4S)-5-([1,1'-Biphenyl]-4-yl)-4-(3-carboxypropanamido)-2-methylpentanoic acid

Similarity: 0.74

Chemical Structure| 1202-66-0

[ 1202-66-0 ]

N-(4-Hydroxyphenethyl)acetamide

Similarity: 0.72

Chemical Structure| 1347675-92-6

[ 1347675-92-6 ]

(R)-N-(Tetrahydro-2H-pyran-3-yl)benzamide

Similarity: 0.71

Chemical Structure| 322407-34-1

[ 322407-34-1 ]

(1S,2S)-2-(Benzylamino)cyclohexanol

Similarity: 0.70