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[ CAS No. 155370-03-9 ] {[proInfo.proName]}

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Chemical Structure| 155370-03-9
Chemical Structure| 155370-03-9
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Product Details of [ 155370-03-9 ]

CAS No. :155370-03-9 MDL No. :MFCD09999181
Formula : C15H12FNO Boiling Point : -
Linear Structure Formula :- InChI Key :HQCCOFMBOJBRQY-UHFFFAOYSA-N
M.W : 241.26 Pubchem ID :16748770
Synonyms :

Calculated chemistry of [ 155370-03-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.13
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 71.21
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 3.02
Log Po/w (WLOGP) : 3.09
Log Po/w (MLOGP) : 2.86
Log Po/w (SILICOS-IT) : 3.64
Consensus Log Po/w : 2.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.67
Solubility : 0.0521 mg/ml ; 0.000216 mol/l
Class : Soluble
Log S (Ali) : -3.3
Solubility : 0.122 mg/ml ; 0.000506 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.74
Solubility : 0.000439 mg/ml ; 0.00000182 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.4

Safety of [ 155370-03-9 ]

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 [ 155370-03-9 ]

* 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 [ 155370-03-9 ]
  • Downstream synthetic route of [ 155370-03-9 ]

[ 155370-03-9 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 156492-25-0 ]
  • [ 155370-03-9 ]
YieldReaction ConditionsOperation in experiment
96% With K-10 clay In neat (no solvent) at 85℃; for 0.0833333 h; Microwave irradiation General procedure: (2E)-1-(2-aminophenyl)-3-(2-fluorophenyl)prop-2-en-1-one (1), (2E)-1-(2-aminophenyl)-3-(3-fluorophenyl)prop-2-en-1-one (2), and (2E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (3) (0.02 mol each) were dissolved in chloroform and uniformly adsorbed on the surface of K-10 clay (15 g each) in a Pyrex round bottomed flask. The solvent was evaporated under vacuum, and then the adsorbed material was transferred to a Pyrextube (2 cm diameter, 30 mL) and inserted inside the Milestone microwave oven. The mixture was heated using axed power of 350 W for 5 min at 85° C. The reaction mixture was dissolved in AcOEt (2 15 mL) and filtered off. The extract was evaporated to leave a crude mixture, which was purified by column chromatography over silica (hexane{AcOEt, 5:1) to afford the pure corresponding products (4, 5, and 6) in 92percent, 90percent, and 96percent yields,respectively; the assigned structures for the known compounds 2-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one(4), 2-(3-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (5), and 2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (6) were confirmed by their spectral properties (1 H, 13C/APT, 2D-COSY NMR, IR, and LC-MS/MS )and by comparison with literature data.
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 1, p. 13 - 15
[2] Turkish Journal of Chemistry, 2015, vol. 39, # 4, p. 850 - 866
[3] South African Journal of Chemistry, 1994, vol. 47, # 1, p. 21 - 25
[4] RSC Advances, 2015, vol. 5, # 103, p. 85128 - 85138
[5] Tetrahedron Letters, 2006, vol. 47, # 16, p. 2725 - 2729
[6] Journal of Chemical Research, Miniprint, 1994, # 2, p. 367 - 382
  • 2
  • [ 262606-35-9 ]
  • [ 155370-03-9 ]
YieldReaction ConditionsOperation in experiment
94% With zirconyl(IV) nitrate hydrate In ethanol; water at 50℃; for 3 h; Green chemistry General procedure: A mixture of the appropriate 2-aminochalcone (1 mmol), EtOH(2 mL), H2O (2 mL), and ZrO(NO3)2·nH2O (46 mg, 20 molpercent) washeated with stirring at 50 °C while the progress of the reactionwas monitored by TLC. The reaction was then quenched withH2O (5 mL), and the mixture was extracted with Et2O (3 × 10mL). The combined organic extracts were washed with brine (5mL) then dried (Na2SO4), filtered, and concentrated underreduced pressure. The crude product was purified by columnchromatography [silica gel, hexane–EtOAc (10:1)]. 2-Phenyl-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry1)5b,6b,11Off-white solid; yield: 218 mg (98percent); mp 153–155 °C. IR (KBr):3060, 3028, 1638, 1572, 1494, 1358, 1324, 1295, 1157, 1095,974, 861 cm–1. 1H NMR (600 MHz, CDCl3): δ = 7.83 (dd, J = 8.5,1.2 Hz, 1 H), 7.42 (d, J = 7.4 Hz, 2 H), 7.40–7.36 (m, 2 H), 7.35–7.33 (m, 2 H), 6.76 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 8.5 Hz, 1 H),4.70 (dd, J = 13.5, 3.6 Hz, 1 H), 4.65 (s, 1 H, NH), 2.82 (dd, J =16.3, 14.4 Hz, 1 H), 2.70 (dd, J = 15.6, 3.6 Hz, 1 H). 13C NMR (150MHz, CDCl3): δ = 192.9, 152.4, 136.1, 128.6, 128.3, 127.4, 126.5,119.2, 117.2, 116.7, 59.1, 45.7. MS (EI): m/z = 223.10 [M+].
Reference: [1] Synthetic Communications, 2010, vol. 40, # 4, p. 476 - 481
[2] Synthetic Communications, 2010, vol. 40, # 9, p. 1391 - 1398
[3] Synlett, 2018, vol. 29, # 2, p. 235 - 237
[4] Journal of Heterocyclic Chemistry, 2016, vol. 53, # 6, p. 2111 - 2122
  • 3
  • [ 459-57-4 ]
  • [ 551-93-9 ]
  • [ 155370-03-9 ]
YieldReaction ConditionsOperation in experiment
94% With C22H48N4O12S4(4+)*4HO4S(1-) In ethanol; water at 20℃; for 1.6 h; Irradiation; Reflux 1 mmol of p-fluorobenzaldehyde, 1 mmol of o-aminoacetophenone and 0.09 mmol of high acidity ionic liquid were separately added to a 50 ml one-necked flask with a condenser tube containing 8 ml of 95percent aqueous ethanol and stirred at room temperature. Heating and refluxing, ultrasonic irradiation under the reaction for 1.6h, TLC (thin plate chromatography) detection, the disappearance of raw materials, the end of the reaction cooled to room temperature to precipitate a large number of solid, put it into the ice bath to continue cooling the solid, the amount of solid is no longer increased The precipitated solid was allowed to stand, suction, and the residue was washed with absolute ethanol (3 ml x 3) and dried in vacuo at 75 ° C to give2- (4-fluoro) -phenyl-2,3-dihydro-4 (1H) -quinolinone,The purity was 99.0percent and the yield was 94percent by high performance liquid chromatography. The filtrate is directly added to the fluorobenzaldehyde, o-amino acetophenone after repeated use.
85% With silver trifluoromethanesulfonate In methanol for 18 h; Reflux; Inert atmosphere General procedure: AgOTf (26 mg, 10 molpercent) was added to a solution of an o-aminoacetophenone (1.0 mmol) and an aryl aldehyde (1.2 mmol) in MeOH (5mL) at r.t. The reaction mixture was stirred under reflux for 12–24 h. After the reaction was complete, as indicated by TLC, the excess solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexanes–EtOAc, 20:1) to yield the desired product.
Reference: [1] Patent: CN107162970, 2017, A, . Location in patent: Paragraph 0050; 0051; 0052
[2] Synthesis (Germany), 2015, vol. 47, # 24, p. 3881 - 3890
[3] Tetrahedron Letters, 2007, vol. 48, # 28, p. 4935 - 4937
[4] Tetrahedron Letters, 2016, vol. 57, # 49, p. 5442 - 5445
  • 4
  • [ 1425928-63-7 ]
  • [ 155370-03-9 ]
Reference: [1] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 327 - 334
  • 5
  • [ 551-93-9 ]
  • [ 155370-03-9 ]
Reference: [1] South African Journal of Chemistry, 1994, vol. 47, # 1, p. 21 - 25
[2] Journal of Chemical Research, Miniprint, 1994, # 2, p. 367 - 382
[3] Archiv der Pharmazie, 2013, vol. 346, # 1, p. 7 - 16
[4] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 327 - 334
[5] Turkish Journal of Chemistry, 2015, vol. 39, # 4, p. 850 - 866
  • 6
  • [ 459-57-4 ]
  • [ 155370-03-9 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1994, # 2, p. 367 - 382
[2] Turkish Journal of Chemistry, 2015, vol. 39, # 4, p. 850 - 866
  • 7
  • [ 5234-26-4 ]
  • [ 155370-03-9 ]
Reference: [1] Archiv der Pharmazie, 2013, vol. 346, # 1, p. 7 - 16
[2] Letters in Drug Design and Discovery, 2013, vol. 10, # 4, p. 327 - 334
  • 8
  • [ 118-92-3 ]
  • [ 155370-03-9 ]
Reference: [1] Archiv der Pharmazie, 2013, vol. 346, # 1, p. 7 - 16
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