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[ CAS No. 396-30-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 396-30-5
Chemical Structure| 396-30-5
Chemical Structure| 396-30-5
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Product Details of [ 396-30-5 ]

CAS No. :396-30-5 MDL No. :MFCD01685512
Formula : C9H6FN Boiling Point : -
Linear Structure Formula :- InChI Key :RMDCSDVIVXJELQ-UHFFFAOYSA-N
M.W : 147.15 Pubchem ID :196975
Synonyms :

Calculated chemistry of [ 396-30-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.7
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.85
Log Po/w (XLOGP3) : 2.06
Log Po/w (WLOGP) : 2.79
Log Po/w (MLOGP) : 2.27
Log Po/w (SILICOS-IT) : 2.91
Consensus Log Po/w : 2.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.72
Solubility : 0.279 mg/ml ; 0.00189 mol/l
Class : Soluble
Log S (Ali) : -1.96
Solubility : 1.62 mg/ml ; 0.011 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.96
Solubility : 0.0162 mg/ml ; 0.00011 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 396-30-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 396-30-5 ]

* 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 [ 396-30-5 ]
  • Downstream synthetic route of [ 396-30-5 ]

[ 396-30-5 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 59611-52-8 ]
  • [ 396-30-5 ]
YieldReaction ConditionsOperation in experiment
97% With diethylazodicarboxylate In chloroform; toluene at 20℃; for 12 h; 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.
68% 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.
Reference: [1] Organic Letters, 2015, vol. 17, # 18, p. 4404 - 4407
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 11, p. 3080 - 3084[3] Angew. Chem., 2017, vol. 129, # 11, p. 3126 - 3130,5
[4] Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303
[5] Synthetic Communications, 2018, vol. 48, # 11, p. 1291 - 1298
[6] Chemistry - A European Journal, 2017, vol. 23, # 57, p. 14167 - 14172
[7] Organic Letters, 2018, vol. 20, # 20, p. 6436 - 6439
[8] Tetrahedron Letters, 2018, vol. 59, # 10, p. 949 - 953
[9] Patent: CN107141252, 2017, A, . Location in patent: Paragraph 0048; 0049; 0050; 0051; 0052
  • 2
  • [ 56-81-5 ]
  • [ 371-40-4 ]
  • [ 396-30-5 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 41, p. 21456 - 21464
[2] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 16967 - 16970,4
[3] Journal of the American Chemical Society, 2012, vol. 134, # 41, p. 16967 - 16970
[4] Journal of Molecular Structure, 2003, vol. 661-662, # 1-3, p. 209 - 218
[5] Patent: WO2009/87649, 2009, A1, . Location in patent: Page/Page column 24
[6] Angewandte Chemie - International Edition, 2016, vol. 55, # 41, p. 12891 - 12894[7] Angew. Chem., 2016, vol. 128, p. 13083 - 13086,4
  • 3
  • [ 1227828-28-5 ]
  • [ 396-30-5 ]
YieldReaction ConditionsOperation in experiment
60% With Selectfluor; barium(II) oxide; silver(l) oxide In acetone at 23 - 90℃; for 2 h; To aryl silane (0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23 °C were added silver oxide (69.6 mg, 0.300 mmol, 3.00 equiv), barium oxide (17.2 mg, 0.110 mmol, 1.10 equiv), and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) (1) (70.8 mg, 0.200 mmol, 2.00 equiv). The reaction mixture was stirred for 2 h at 90 °C in a sealed vial. The reaction mixture was cooled to 23 °C, passed through a pad of Celite and concentrated under reduced pressure. To the residue was added CH2Cl2 (20 mL) and a saturated aqueous solution of NaHCO3 (20 mL). The organic phase was separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on preparative TLC.
Reference: [1] Tetrahedron, 2011, vol. 67, # 24, p. 4449 - 4454
  • 4
  • [ 173089-80-0 ]
  • [ 396-30-5 ]
Reference: [1] Science, 2009, vol. 325, # 5948, p. 1661 - 1664
[2] Journal of the American Chemical Society, 2009, vol. 131, p. 1662 - 1663
[3] Tetrahedron, 2011, vol. 67, # 24, p. 4449 - 4454
  • 5
  • [ 580-15-4 ]
  • [ 396-30-5 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1785
[2] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 10
  • 6
  • [ 5332-25-2 ]
  • [ 396-30-5 ]
Reference: [1] Applied Catalysis A: General, 2011, vol. 394, # 1-2, p. 191 - 194
  • 7
  • [ 3054-95-3 ]
  • [ 371-40-4 ]
  • [ 396-30-5 ]
YieldReaction ConditionsOperation in experiment
29.6 %Chromat. With Ni-modified Beta zeolite In neat (no solvent) for 0.0833333 h; Microwave irradiation; Reflux; Green chemistry General procedure: General procedure for synthesis of quinolines from anilines and ADA was carried out in Panasonic NN-K5541JF microwave oven reactor equipping a magnetic stirring device. The typical procedures were as follows: ADA (1mmol), excessive anilines (4mmol) and solid catalyst were charged into a round-bottom ask; and then, the mixtures was placed into microwave reactor. The reaction was conducted by continuous microwave irradiation for 1–40 min under refluxing and stirring condition. Finally, the resulting products were determined by GC–MS of Varian Saturn 2200/ CP-3800 gas chromatography–mass spectrometry equipped with two CP8944 capillary columns (VF-5,30m×0.25mm×0.25 μm).
Reference: [1] Catalysis Communications, 2018, vol. 115, p. 21 - 25
  • 8
  • [ 624-67-9 ]
  • [ 371-40-4 ]
  • [ 396-30-5 ]
Reference: [1] Chemistry - An Asian Journal, 2014, vol. 9, # 11, p. 3089 - 3093
  • 9
  • [ 107-02-8 ]
  • [ 371-40-4 ]
  • [ 396-30-5 ]
Reference: [1] Chemistry - An Asian Journal, 2014, vol. 9, # 11, p. 3089 - 3093
  • 10
  • [ 2338-74-1 ]
  • [ 396-30-5 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 32, p. 7035 - 7038
  • 11
  • [ 580-16-5 ]
  • [ 396-30-5 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 30, p. 11482 - 11484
[2] Patent: WO2012/142162, 2012, A2, . Location in patent: Page/Page column 24
  • 12
  • [ 91-22-5 ]
  • [ 396-30-5 ]
  • [ 394-68-3 ]
  • [ 394-69-4 ]
  • [ 16650-32-1 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 117, # 2, p. 99 - 101
  • 13
  • [ 394-70-7 ]
  • [ 56-81-5 ]
  • [ 396-30-5 ]
Reference: [1] Journal of Organic Chemistry, 1951, vol. 16, p. 1450
  • 14
  • [ 60144-53-8 ]
  • [ 1611-78-5 ]
  • [ 396-30-5 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7288 - 7291
  • 15
  • [ 60144-53-8 ]
  • [ 927-63-9 ]
  • [ 396-30-5 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 26, p. 7288 - 7291
  • 16
  • [ 91-22-5 ]
  • [ 396-30-5 ]
  • [ 394-68-3 ]
  • [ 394-69-4 ]
  • [ 16650-32-1 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 117, # 2, p. 99 - 101
  • 17
  • [ 91-22-5 ]
  • [ 396-30-5 ]
  • [ 394-68-3 ]
  • [ 394-69-4 ]
  • [ 16650-32-1 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 117, # 2, p. 99 - 101
  • 18
  • [ 396-30-5 ]
  • [ 59611-52-8 ]
YieldReaction ConditionsOperation in experiment
71.6% at 20℃; for 12 h; Sodium cyanoborohydride (6.45 g, 103 mmol ) was added gradually to the solution of 6-fluoro quinoline (5 g, 34 mmol) in glacial acetic acid (100 ml) at ambient temperature. After stirring for 12 h the reaction mixture was quenched in water and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with water, brine and dried over sodium sulfate, filtered and evaporated in vacuo, the residue was purified by a silica gel column with 1 percent to 5percent ethyl acetate in petroleum ether to afford 6-fluoro- 1 , 2,3, 4-tetrahydroquinoline as a light yellow liquid (3.65 g, 71.6 percent).LC/MS (ES, m/z): [M+H]+ 152.0'H-NMR (300 MHz, CDC13): δ 6.68 - 6.74 (m, 2H), 6.43 - 6.48 (m, 1H), 3.27 - 3.31 (m, 2H), 2.74 - 2.79 (t, 7 = 6.6 Hz, 2H), 1.91 - 1.99(m, 2H)
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15656 - 15661[2] Angew. Chem., 2016, vol. 128, # 50, p. 15885 - 15890,6
[3] ACS Catalysis, 2018, vol. 8, # 5, p. 4545 - 4557
[4] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17592 - 17598,7
[5] Advanced Synthesis and Catalysis, 2015, vol. 357, # 4, p. 753 - 760
[6] Patent: WO2012/94462, 2012, A2, . Location in patent: Page/Page column 45
[7] Organic Letters, 2015, vol. 17, # 18, p. 4404 - 4407
[8] Journal of Fluorine Chemistry, 2001, vol. 111, # 1, p. 1 - 10
[9] Patent: WO2009/87649, 2009, A1, . Location in patent: Page/Page column 24
[10] Patent: EP2172453, 2010, A1, . Location in patent: Page/Page column 10
[11] Green Chemistry, 2017, vol. 19, # 3, p. 749 - 756
[12] Tetrahedron Letters, 2018, vol. 59, # 10, p. 949 - 953
[13] Organic Letters, 2018, vol. 20, # 4, p. 1171 - 1174
[14] Molecular Catalysis, 2018, vol. 452, p. 145 - 153
[15] Angewandte Chemie - International Edition, 2018, vol. 57, # 31, p. 9950 - 9954[16] Angew. Chem., 2018, vol. 130, p. 10098 - 10102,5
  • 19
  • [ 396-30-5 ]
  • [ 86324-51-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1983, vol. 26, # 9, p. 1267 - 1277
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