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[ CAS No. 22190-35-8 ] {[proInfo.proName]}

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Chemical Structure| 22190-35-8
Chemical Structure| 22190-35-8
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Product Details of [ 22190-35-8 ]

CAS No. :22190-35-8 MDL No. :MFCD04966989
Formula : C9H10BrN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 212.09 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 22190-35-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.04
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) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.25
Log Po/w (XLOGP3) : 2.98
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.78
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.44
Solubility : 0.0777 mg/ml ; 0.000366 mol/l
Class : Soluble
Log S (Ali) : -2.9
Solubility : 0.269 mg/ml ; 0.00127 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.14
Solubility : 0.0154 mg/ml ; 0.0000728 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.69

Safety of [ 22190-35-8 ]

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 [ 22190-35-8 ]

* 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 [ 22190-35-8 ]
  • Downstream synthetic route of [ 22190-35-8 ]

[ 22190-35-8 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 22190-35-8 ]
  • [ 5332-25-2 ]
YieldReaction ConditionsOperation in experiment
97% With diethylazodicarboxylate In chloroform; toluene for 12 h; Reflux General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar, 1,2,3,4-tetrahydroquinoline (0.5 mmol), DEAD solution 40 wtpercent in toluene (2.2 eq, 1.1 mmol, 0.5 mL), and CHCl3 (1.0 mL) was added. The reaction mixture was stirred at room temperature for 12 h. The mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with EtOAc:hexane (1:5) to give quinolines. In case of 2f and 2m, the product spot was close to the spot of the remained DEAD. To eliminate the remained DEAD, 1 equivalent of PPh3 was added after the reaction and the reaction mixture was stirred.[19] After 10 min, the reaction mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with CHCl3:hexane (1:1) to give quinolines.
78% With cobalt(II) 5,10,15,20-tetraphenylporphyrin; oxygen In N,N-dimethyl-formamide for 12 h; General procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for 1H and 100 MHz for 13C, using CDCl3 as solvent with TMS as the internal standard. Thin-layer chromatography was performed on silica gel 60 F254 (Sinopharm) thin-layer chromatography plates using petroleum ether/ethyl acetate (10:1 v/v) as the mobile phase.
71% With oxygen; iron(II) chloride In para-xylene; dimethyl sulfoxide at 110℃; for 26 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] Organic Letters, 2015, vol. 17, # 18, p. 4404 - 4407
[2] Synthetic Communications, 2018, vol. 48, # 11, p. 1291 - 1298
[3] Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14167 - 14172
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 11, p. 3080 - 3084[5] Angew. Chem., 2017, vol. 129, # 11, p. 3126 - 3130,5
[6] Journal of the American Chemical Society, 2015, vol. 137, # 33, p. 10652 - 10658
[7] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[8] Tetrahedron Letters, 2018, vol. 59, # 10, p. 949 - 953
[9] Synlett, 2016, vol. 27, # 12, p. 1806 - 1809
[10] Tetrahedron, 2008, vol. 64, # 43, p. 10068 - 10074
[11] ACS Catalysis, 2018, vol. 8, # 2, p. 1192 - 1196
[12] Organic Letters, 2018, vol. 20, # 20, p. 6436 - 6439
[13] Tetrahedron, 2017, vol. 73, # 36, p. 5389 - 5396
[14] Patent: CN107141252, 2017, A, . Location in patent: Paragraph 0048; 0049; 0050; 0051; 0052
  • 2
  • [ 5332-25-2 ]
  • [ 22190-35-8 ]
YieldReaction ConditionsOperation in experiment
84% With ethanol; Dimethylphenylsilane; Au-TiO2 In neat (no solvent) at 70℃; for 3 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).
Reference: [1] Chemical Communications, 2013, vol. 49, # 63, p. 7052 - 7054
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3216 - 3220[3] Angew. Chem., 2017, vol. 129, # 12, p. 3264 - 3268,5
[4] ChemCatChem, 2017, vol. 9, # 13, p. 2496 - 2505
[5] Advanced Synthesis and Catalysis, 2015, vol. 357, # 16-17, p. 3529 - 3537
[6] Journal of the American Chemical Society, 2011, vol. 133, # 19, p. 7547 - 7562
[7] Arkivoc, 2015, vol. 2015, # 3, p. 38 - 51
[8] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 1981 - 1985
[9] Organometallics, 2013, vol. 32, # 16, p. 4501 - 4506
[10] Journal of Materials Chemistry A, 2017, vol. 5, # 7, p. 3260 - 3266
[11] Journal of the American Chemical Society, 2017, vol. 139, # 28, p. 9419 - 9422
[12] Tetrahedron Letters, 2018, vol. 59, # 10, p. 949 - 953
[13] Catalysis Science and Technology, 2018, vol. 8, # 19, p. 5019 - 5097
  • 3
  • [ 635-46-1 ]
  • [ 22190-35-8 ]
YieldReaction ConditionsOperation in experiment
35% With N-Bromosuccinimide In tetrachloromethane at 0℃; for 3 h; NBS (28 g, 158 mmol) was added to a solution of 1,2,3,4-tetrahydroquinoline (20 g, 150.16 mmol) in carbon tetrachloride (200 mL). The resulting solution was stirred for 3 h at 0°C, extracted with dichloromethane(3 x 50 mL) and concentrated in vacuo to give a residue, which was applied onto a silica gel column with 1 percent ethyl acetate in petroleum ether to give 6-bromo- 1 ,2,3,4-tetrahydroquinoline as a yellow solid (11 g, 35percent).LC/MS(ES, m/z):[M+H]+ 212.1'H-NMR (300 MHz, CDC13) δ 7.03 - 7.07 (m, 2H), 6.35 - 6.38 (m, 1H), 3.51 - 3.55 (m, 2H), 2.73- 2.80 (m, 2H), 1.89 - 1.99 (m, 2H)
20 g With N-Bromosuccinimide In acetonitrile at 0℃; for 4 h; Reaction step 1
Synthesis of 6-bromo-1,2,3,4-tetrahydroquinoline
To a stirred solution of 1,2,3,4-tetrahydroquinoline (20.0 g, 150 mmol, 1.0 eq) in acetonitrile, N-bromosuccinimide (25.5 g, 143 mmol, 0.95 eq) was added in four equal portions at 0° C., in an interval of 20 min between each portion.
Stirring was continued at 0° C. for 3 h.
After completion of the reaction (monitored by TLC, 10percent ethyl acetate-hexane, Rf=0.55), diethyl ether was added and the mixture was washed with saturated sodium bicarbonate solution followed by water and brine.
The organic extract was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure.
The crude product was purified by column chromatography on silica gel (100-200 mesh), eluting with 5percent ethyl acetate in hexanes to obtain 6-bromo-1,2,3,4-tetrahydroquinoline (20.0 g, 64percent) as yellow oil. LCMS: Purity: 92.25percent (ES+): m/z 212.0 (M+H+); tr=2.06 min.
Reference: [1] Tetrahedron, 2005, vol. 61, # 16, p. 4035 - 4041
[2] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 60
[3] Patent: US2008/221160, 2008, A1, . Location in patent: Page/Page column 11; 12
[4] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 11
[5] Patent: WO2013/166015, 2013, A1, . Location in patent: Paragraph 0093 - 0095
[6] Patent: US2015/252022, 2015, A1, . Location in patent: Paragraph 0374
[7] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[8] Tetrahedron, 2017, vol. 73, # 36, p. 5389 - 5396
[9] Patent: US2016/24056, 2016, A1, . Location in patent: Paragraph 0243
  • 4
  • [ 3279-90-1 ]
  • [ 22190-35-8 ]
Reference: [1] Patent: US2004/220206, 2004, A1, . Location in patent: Page 24; 32
  • 5
  • [ 5332-25-2 ]
  • [ 635-46-1 ]
  • [ 22190-35-8 ]
Reference: [1] Synlett, 2004, # 15, p. 2827 - 2829
  • 6
  • [ 76228-06-3 ]
  • [ 22190-35-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 23, p. 6481 - 6488
  • 7
  • [ 67-63-0 ]
  • [ 22190-35-8 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 16, p. 3215 - 3217
  • 8
  • [ 185122-63-8 ]
  • [ 22190-35-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 7956 - 7967
  • 9
  • [ 635-46-1 ]
  • [ 22190-35-8 ]
  • [ 190843-73-3 ]
Reference: [1] Tetrahedron, 2008, vol. 64, # 43, p. 10068 - 10074
  • 10
  • [ 22190-35-8 ]
  • [ 5382-49-0 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 16, p. 4035 - 4041
  • 11
  • [ 22190-35-8 ]
  • [ 557-21-1 ]
  • [ 50741-36-1 ]
YieldReaction ConditionsOperation in experiment
80% at 120℃; for 2 h; To a solution of 6-bromo-l,2,3,4-tetrahydroquinoline (10 g, 47.15 mmol) in N,N- dimethylformamide (80 mL) was added Pd(PPh3)4 (2.8 g, 2.42 mmol), and zincdicarbonitrile (6.4 g, 54.49 mmol) and the reaction was stirred for 2 h at 120°C in an oil bath. The reaction was quenched by the addition of water (400 mL) and extracted with dichloromethane(3 x 50 mL), and concentrated in vacuo to give a residue, which was purified by a silica gel chromatography with 1 percent - 20 percent ethyl acetate in petroleum ether to give l,2,3,4-tetrahydroquinoline-6-carbonitrile as a yellow solid (6 g, 80 percent).LC/MS (ES, m/z): [M+H]+ 159.1'H-NMR (300 MHz, CDC13) δ 7.20 - 7.23 (m, 2H), 6.40 (d, 7 = 8.1 Hz, 1H), 3.36 - 3.40 (t, 7 = 5.7 Hz, 2H), 2.72 - 2.77 (t, 7 = 6.3 Hz, 2H), 1.90 - 1.97 (m, 2H)
Reference: [1] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 60-61
[2] Patent: US2004/220206, 2004, A1, . Location in patent: Page 24; 32
  • 12
  • [ 22190-35-8 ]
  • [ 50741-36-1 ]
Reference: [1] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 11
  • 13
  • [ 22190-35-8 ]
  • [ 544-92-3 ]
  • [ 50741-36-1 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 16, p. 4035 - 4041
  • 14
  • [ 22190-35-8 ]
  • [ 24424-99-5 ]
  • [ 1123169-45-8 ]
YieldReaction ConditionsOperation in experiment
40.7% With sodium hydroxide In tetrahydrofuran; water at 20℃; for 12 h; [00336] Step 1. To a stirred solution of bromo-tetrahydroquinoline 1-A (5 g, 23.7 mmol) in 60 mL of THF was added a solution of NaOH (lg, 25 mmol) in H20 (30 mL). Ditertbutyl dicarbonate (5.37 g, 25 mmol) was added. The mixture was stirred for 12 hours at room temperature. Solvent was removed in vacuo, and the aqueous mixture was extracted with EtOAc (50 mL x 3). The combined organic extracts were washed with brine, dried over anhydrous Na2S04, concentrated and purified with column chromatography to provide the boc-protected compound 17-A as a colorless solid (3 g, 40.7percent). 1H NMR (300 MHz, CDC13): δ 7.56 - 7.53 (m, 1H), 7.24 - 7.19 (m, 2H), 3.70 - 3.66 (m, 2H), 2.75 - 2.71 (m, 2H), 1.92 - 1.88 (m, 2H), 1.52 (s, 9H).
Reference: [1] ChemMedChem, 2018, vol. 13, # 14, p. 1405 - 1413
[2] Patent: WO2014/8214, 2014, A1, . Location in patent: Paragraph 00335-00336
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