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[ CAS No. 42835-89-2 ] {[proInfo.proName]}

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Chemical Structure| 42835-89-2
Chemical Structure| 42835-89-2
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Product Details of [ 42835-89-2 ]

CAS No. :42835-89-2 MDL No. :MFCD00040976
Formula : C10H12FN Boiling Point : -
Linear Structure Formula :- InChI Key :BDCCXYVTXRUGAN-UHFFFAOYSA-N
M.W : 165.21 Pubchem ID :591684
Synonyms :

Calculated chemistry of [ 42835-89-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 51.11
TPSA : 12.03 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.26
Log Po/w (XLOGP3) : 2.83
Log Po/w (WLOGP) : 2.42
Log Po/w (MLOGP) : 2.78
Log Po/w (SILICOS-IT) : 2.88
Consensus Log Po/w : 2.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.02
Solubility : 0.159 mg/ml ; 0.000961 mol/l
Class : Soluble
Log S (Ali) : -2.74
Solubility : 0.3 mg/ml ; 0.00182 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.71
Solubility : 0.0325 mg/ml ; 0.000197 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 42835-89-2 ]

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 [ 42835-89-2 ]

* 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 [ 42835-89-2 ]
  • Downstream synthetic route of [ 42835-89-2 ]

[ 42835-89-2 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 42835-89-2 ]
  • [ 87-13-8 ]
  • [ 42835-25-6 ]
Reference: [1] Patent: US4301288, 1981, A,
[2] Patent: US4301289, 1981, A,
[3] Patent: US4301291, 1981, A,
  • 2
  • [ 42835-89-2 ]
  • [ 42835-25-6 ]
Reference: [1] Patent: US4301288, 1981, A,
[2] Patent: US4301289, 1981, A,
[3] Patent: US4301291, 1981, A,
  • 3
  • [ 15568-85-1 ]
  • [ 42835-89-2 ]
  • [ 123400-74-8 ]
  • [ 42835-25-6 ]
Reference: [1] Patent: EP310849, 1989, A1,
  • 4
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  • [ 42835-25-6 ]
Reference: [1] Tetrahedron Asymmetry, 1999, vol. 10, # 6, p. 1079 - 1087
[2] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11718 - 11724
  • 5
  • [ 42835-89-2 ]
  • [ 1128-61-6 ]
YieldReaction ConditionsOperation in experiment
52% With oxygen; iron(II) chloride In para-xylene; dimethyl sulfoxide at 110℃; for 24 h; Schlenk technique General procedure: To a Schlenk tube equipped with a magnetic stir bar were added8-methyl-1,2,3,4-tetrohydroquinoline (0.50 mmol), FeCl2 (1.9mg, 1.5·10–2 mmol), DMSO (31.2 mg, 0.4 mmol), and p-xylene (1mL). The reaction mixture was stirred at 110 °C under anoxygen atmosphere using a balloon and monitored by TLC. Afterthe reaction, the mixture was cooled to room temperature andpurified using flash chromatography (hexane–EtOAc, 10:1) togive the corresponding product 8-methylquinoline in 70percent yield.8-MethylquinolineColorless oil. 1H NMR (400 MHz, CDCl3): δ = 8.93 (m, 1 H), 8.10(m, 1 H), 7.64 (d, J = 4.0 Hz, 1 H), 7.54 (m, 1 H), 7.43–7.35 (m, 2H) 2.82 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 149.2, 147.3,137.1, 136.3, 129.6, 128.3, 126.3, 125.9, 120.8, 18.2. HRMS: m/zcalcd for [C10H9N + H+]: 144.0813; found: 144.0813.
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12224 - 12227[2] Angew. Chem., 2016, vol. 128, # 40, p. 12412 - 12415,4
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 6983 - 6987[4] Ross. Khim. Zh., 2013, vol. 125, # 27, p. 7121 - 7125,5
[5] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10652 - 10658
[6] Organometallics, 2018, vol. 37, # 4, p. 584 - 591
[7] Synlett, 2016, vol. 27, # 12, p. 1806 - 1809
  • 6
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  • [ 1128-61-6 ]
  • [ 199186-69-1 ]
Reference: [1] ChemCatChem, 2018, vol. 10, # 11, p. 2374 - 2377
  • 7
  • [ 1128-61-6 ]
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YieldReaction ConditionsOperation in experiment
98% With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 1,2,3,4,5-pentakis(methoxycarbonyl)cyclopentadiene In chloroform at 20℃; for 2 h; General procedure: An oven-dried flask was fitted with magnetic stirring bar and charged with 2-substituted quinoline (0.1 mmol), PCCP (1 molpercent), Hantzsch dihydropyridine (3.0 equiv.) and CHCl3 (2 mL). The resulting mixturewas stirred at room temperature for 2 h. The solvent was removed under reduced pressure and the residuewas purified by column chromatography on silica gel using Hexane/EtOAc (20:1) as eluent to yield thecorresponding 1,2,3,4-tetrahydroquinolines
82% With ethanol; Dimethylphenylsilane; Au-TiO2 In neat (no solvent) at 70℃; for 0.333333 h; General procedure: To a dry vial containing 8-methoxyquinoline, 1 (0.048 g, 0.3 mmol), Me2PhSiH (185 μL, 1.2mmol) and ethanol (70 μL, 1.2 mmol), Au/TiO2 (60 mg, 1.0 molpercent) was added. The Au contentin catalyst was ~1 wtpercent. The mixture was heated to 70 oC and the progress of reaction wasmonitored by TLC and GC. After 15 min (100percent conversion), ethanol (1 mL) was added and theresulting slurry was filtered under reduced pressure through a short pad of silica gel with the aidof ethanol (2-3 mL) to withhold the supported catalyst. The filtrate was evaporated undervacuum and the residue was chromatographed (n-hexane/ethyl acetate, 10:1) to afford 8-methoxy-1,2,3,4-tetrahydroquinoline (1a) (41 mg, 84percent yield).
68% at 20 - 50℃; General procedure: 4.2
(RS)-6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinoline 1a
Metallic sodium (3.5 g) was added portionwise to a stirred solution of 6-fluoro-2-methylquinoline (2.0 g, 12.4 mmol) in EtOH (40 mL) at 50 °C.
The reaction mixture was stirred at 50 °C for 3 h and kept at ambient temperature overnight.
Then, water (100 mL) and concentrated HCl (20 mL) were added, and the reaction mixture was concentrated to a volume of 110 mL, washed with benzene (2 * 20 mL), alkalized with NaOH to pH 9-10, and extracted with benzene (3 * 20 mL).
Organic layer was dried over MgSO4 and evaporated under reduced pressure.
The residue was purified by flash column chromatography on silica gel using benzene as an eluent.
Yield 1.4 g (68percent).
Colorless solid, mp 34-36 °C. 1H NMR (500 MHz): δ 1.12 (3H, d, J 6.3 Hz, Me), 1.39 (1H, dddd, J 12.6, 11.3, 9.5, 5.2 Hz, H-3B), 1.82 (1H ddt, J 12.6, 5.8, 3.2 Hz, , H-3A), 2.61 (1H, ddd, J 16.7, 5.2, 3.7 Hz, H-4B), 2.72 (1H, ddd, J 16.7, 11.3, 5.8 Hz, H-4A), 3.24 (1H, dqd, J 9.5, 6.3, 3.1 Hz, H-2), 5.63 (1H, br s, NH), 6.43 (1H, m, H-8), 6.65-6.70 (2H, m, H-5, H-7).
13C NMR (126 MHz): δ 21.88 (Me), 25.96 (C-4), 29.22 (C-3), 46.21 (C-2), 112.63 (d, 2JCF 22.0 Hz, C-7), 114.06 (d, 3JCF 7.4 Hz, C-8), 114.62 (d, 2JCF 21.2 Hz, C-5), 121.15 (d, 3JCF 6.8 Hz, C-4a), 141.60 (C-8a), 154.91 (d, 1JCF 230.8 Hz, C-6).
19F NMR (376 MHz): δ 32.50 (td, J = 9.1, 5.2 Hz, F-6). Anal. Calcd for C10H12FN (M 165.21): C 72.70, H 7.32, F 11.50, N 8.48. Found: C 72.63, H 7.15, F 11.16, N 8.58.
Reference: [1] Synlett, 2008, # 6, p. 900 - 902
[2] Tetrahedron Letters, 2017, vol. 58, # 21, p. 2050 - 2053
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 11, p. 1183 - 1187
[4] Chemistry - A European Journal, 2015, vol. 21, # 14, p. 5370 - 5379
[5] Journal of the American Chemical Society, 2015, vol. 137, # 36, p. 11718 - 11724
[6] Chemical Science, 2018, vol. 9, # 42, p. 8134 - 8141
[7] Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3216 - 3220[8] Angew. Chem., 2017, vol. 129, # 12, p. 3264 - 3268,5
[9] Journal of Organometallic Chemistry, 2007, vol. 692, # 14, p. 3065 - 3069
[10] Synlett, 2006, # 7, p. 1071 - 1074
[11] ACS Catalysis, 2018, vol. 8, # 5, p. 4545 - 4557
[12] Arkivoc, 2015, vol. 2015, # 3, p. 38 - 51
[13] Chemistry - A European Journal, 2012, vol. 18, # 31, p. 9525 - 9529
[14] Angewandte Chemie - International Edition, 2016, vol. 55, # 1, p. 292 - 296[15] Angew. Chem., 2016,
[16] Tetrahedron Asymmetry, 2013, vol. 24, # 19, p. 1240 - 1246
[17] Chemical Communications, 2018, vol. 54, # 62, p. 8622 - 8625
[18] Angewandte Chemie, International Edition, 2009, vol. 48, # 35, p. 6524 - 6528[19] Angewandte Chemie, 2009, vol. 121, # 35, p. 6646 - 6650
[20] Journal of the American Chemical Society, 2016, vol. 138, # 37, p. 12234 - 12242
[21] Angewandte Chemie - International Edition, 2017, vol. 56, # 3, p. 812 - 815[22] Angew. Chem., 2017, vol. 129, # 3, p. 830 - 833,4
[23] Chemical Science, 2017, vol. 8, # 12, p. 8164 - 8169
  • 8
  • [ 123-73-9 ]
  • [ 371-40-4 ]
  • [ 42835-89-2 ]
Reference: [1] Patent: US4301289, 1981, A,
[2] Patent: US4301291, 1981, A,
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