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[ CAS No. 612-57-7 ] {[proInfo.proName]}

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Chemical Structure| 612-57-7
Chemical Structure| 612-57-7
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Product Details of [ 612-57-7 ]

CAS No. :612-57-7 MDL No. :MFCD00024024
Formula : C9H6ClN Boiling Point : -
Linear Structure Formula :- InChI Key :GKJSZXGYFJBYRQ-UHFFFAOYSA-N
M.W : 163.60 Pubchem ID :69163
Synonyms :

Calculated chemistry of [ 612-57-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.75
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) : -5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 2.73
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 2.42
Log Po/w (SILICOS-IT) : 3.13
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) : -3.25
Solubility : 0.0926 mg/ml ; 0.000566 mol/l
Class : Soluble
Log S (Ali) : -2.65
Solubility : 0.362 mg/ml ; 0.00221 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.31
Solubility : 0.00807 mg/ml ; 0.0000493 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.09

Safety of [ 612-57-7 ]

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 [ 612-57-7 ]

* 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 [ 612-57-7 ]
  • Downstream synthetic route of [ 612-57-7 ]

[ 612-57-7 ] Synthesis Path-Upstream   1~19

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  • [ 341010-40-0 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 49, p. 365
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  • [ 20461-86-3 ]
  • [ 4113-04-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1500 - 1505[2] Angew. Chem., 2017, vol. 129, # 6, p. 1522 - 1527,6
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  • [ 99071-54-2 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 11, p. 2818 - 2821
  • 4
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  • [ 100516-88-9 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 5, p. 1278 - 1281
  • 5
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  • [ 1810-72-6 ]
Reference: [1] Journal of Organic Chemistry, 1944, vol. 9, p. 302,305, 309
[2] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
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  • [ 5470-75-7 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 49, p. 365
[2] Journal fuer Praktische Chemie (Leipzig), 1894, vol. <2> 49, p. 365
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  • [ 49716-18-9 ]
YieldReaction ConditionsOperation in experiment
95% With tetrahydroxydiboron; copper diacetate In acetonitrile at 40℃; for 12 h; 6-chloroquinoline (0.3 mmol, 49 mg)Tetrahydroxy diboron (0.9mmol, 81mg),Cu (OAc) 2 (0.015 mmol, 2.5 mg) was added to 1 mL of acetonitrile,40 ° C for 12 hours,The residue was purified by thin layer chromatography to give 47.6 mg of 6-chloro tetrahydroquinoline in 95percent yield, 98percent purity,
84% With tetrahydroxydiboron; copper diacetate In acetonitrile at 40℃; for 8 h; Schlenk technique General procedure: A 20 mL Schlenk tube was charged with quinoline (1a; 65 mg,0.5 mmol), Cu(OAc)2 (4.5 mg, 0.025 mmol), B2(OH)4 (135 mg,1.5 mmol), and MeCN (2.0 mL). The mixture was stirred at 40 °C for 8 h until the reaction was completed (TLC), then cooled to room temperature and concentrated under reduced pressure. Water (10 mL) was added and the mixture was extracted with EtOAc (3 x 10 mL). The organic phases were combined, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography with petroleum ether/ethyl acetate (8:1) as an eluent to give a brown liquid (2a: 65 mg, 98percent yield).
83% With palladium; hydrogen In acetonitrile at 30℃; for 16 h; To a solution of PdNPore (2.7 mg, 5 molpercent) in acetonitrile (5 mL) was added the substrate 6-chloroquinoline(81.8 mg, 0.5 mmol), hydrogen (5 bar), placed on a magnetic stirrer at 30 ° C for 16 h, column chromatography (silica gel, 200-300Methyl acetate) to give 6-chloro-1,2,3,4-tetrahydroquinoline 69.57 mg in 83percent yield,
79% 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).
78%
Stage #1: With hydrogenchloride; hydrogen In ethanol; water at 20℃;
Stage #2: With sodium hydrogencarbonate In water
To a solution of 6-chloroquinoline (1.5 g, 9.17 mmol) in C2H5OH (50 ml) was added Pt02 (41.5 mg, 0.18 mmol) and concentrated HC1 (0.1 ml) under an atmosphere of hydrogen gas. The reaction was stirred overnight at room temperature, then concentrated in vacuo, diluted with water (100 ml), adjusted to pH 8 with aqueous sodium bicarbonate. The resulting solution was extracted with dichloromethane (3 x 80 ml) and the organic layers were combined, dried over anhydrous magnesium sulfate, concentrated in vacuo to afford 6-chloro-l,2,3,4- tetrahydroquinoline as a colorless oil (1.2 g, 78 ).LC/MS (ES, m/z) [M+H]+ 168.0'H-NMR (300 MHz, CDCI3) δ 6.90 - 6.98 (m, 2H), 6.39 - 6.42 (t, / = 1.2 Hz, 1H), 3.23 - 3.35 (m, 2H), 2.73 - 2.81 (m, 2H), 1.91 - 1.96 (m, 2H)
62% With hydrogen In methanol for 4 h; A flask filled with a mixture of 6-chloroquinoline (12.0 g, 73.3 mmol), PtO2 (2.16 g, 13 mol percent), and MeOH (500 mL, 6.15 M) was flushed with N2 and then equipped with a balloon filled with H2. The reaction was kept under H2 atmosphere and stirred for 4 h. The mixture was filtered through Celite and washed with CH2Cl2. Purification via silica gel chromatography using 50percent CH2Cl2 in hexanes gave 6-chloro-1,2,3,4-tetrahydroquinoline (7.7 g, 62percent). 1H NMR (400 MHz, DMSO-d6) δ 6.85-6.83 (m, 2H), 6.42-6.39 (m, 1H), 5.82 (s, 1H), 3.17-3.13 (m, 2H), 2.64 (t, J=6.3 Hz, 2H), 1.78-1.72 (m, 2H). LC/MS (10percent-99percent CH3CN (0.035percent TFA)/H2O (0.05percent TFA)), m/z: M+1 obs=168.2; tR=1.57 min.

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[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 50, p. 15656 - 15661[3] Angew. Chem., 2016, vol. 128, # 50, p. 15885 - 15890,6
[4] Organic Letters, 2013, vol. 15, # 7, p. 1484 - 1487
[5] Chemical Communications, 2013, vol. 49, # 63, p. 7052 - 7054
[6] Patent: CN106831565, 2017, A, . Location in patent: Paragraph 0103; 0104; 0105; 0106
[7] Tetrahedron Letters, 1987, vol. 28, # 1, p. 77 - 80
[8] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 9, p. 2968 - 2976
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[14] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 1981 - 1985
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[16] Tetrahedron, 2018, vol. 74, # 17, p. 2121 - 2129
[17] Patent: CN106432072, 2017, A, . Location in patent: Paragraph 0056-0063
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17592 - 17598,7
[2] Molecular Catalysis, 2018, vol. 452, p. 145 - 153
  • 9
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  • [ 767-92-0 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 9, p. 5816 - 5822
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  • [ 91-22-5 ]
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 42, p. 17592 - 17598,7
[2] Journal of Materials Chemistry A, 2017, vol. 5, # 7, p. 3260 - 3266
  • 11
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  • [ 67-63-0 ]
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Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 16, p. 3215 - 3217
  • 12
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  • [ 613-50-3 ]
YieldReaction ConditionsOperation in experiment
97% With Tris(3,6-dioxaheptyl)amine; sodium nitrite In <i>tert</i>-butyl alcohol at 130℃; for 24 h; Inert atmosphere EXAMPLE FIFTY-FOUR: General Procdure for Pd-Catalyzed Nitrations of Aryl Chlorides and Aryl Sulfonates (Figures 20 and 21); An oven-dried schlenk tube, which was equipped with a magnetic stir bar and fitted with a rubber septum, was charged with the Pd2(dba)3 (0.5 mol percent), ligand (6, 25, 26, or 27) (1.2 mol percent), and NaNO2 (138 mg, 2.0 mmol) (aryl halides* that were solids at room <n="146"/>temperature were added with the catalyst). The vessel was evacuated and backfilled with argon (this process was repeated a total of 3 times) and then the aryl halide* (1.0 mmol), tris(3,6-dioxaheptyl)amine (5 mol percent), and te/t-butanol (2 mL) were added via syringe. The reaction vessel was sealed with a Teflon screw cap and heated to 110 0C for 24 h. The solution was cooled to room temperature, diluted with Ethyl acetate, washed with water, and purified via flash chromatography.* Includes aryltriflates and arylnonaflates.
Reference: [1] Patent: WO2009/76622, 2009, A2, . Location in patent: Page/Page column 144-145
[2] Journal of the American Chemical Society, 2009, vol. 131, # 36, p. 12898 - 12899
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Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 13, p. 6794 - 6813
[2] Journal of the American Chemical Society, 2007, vol. 129, # 43, p. 13001 - 13007
  • 14
  • [ 67-56-1 ]
  • [ 612-57-7 ]
  • [ 201230-82-2 ]
  • [ 38896-30-9 ]
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  • 15
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  • [ 59394-30-8 ]
Reference: [1] Patent: US4461896, 1984, A,
  • 16
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  • [ 64-17-5 ]
  • [ 201230-82-2 ]
  • [ 73987-38-9 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 18, p. 7096 - 7101
  • 17
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  • [ 86984-32-9 ]
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[5] Patent: US5362878, 1994, A,
[6] Patent: WO2008/137027, 2008, A2, . Location in patent: Page/Page column 96
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  • [ 68527-66-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1894, vol. &lt;2&gt; 49, p. 365
  • 19
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  • [ 73183-34-3 ]
  • [ 406463-06-7 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 4, p. 541 - 543
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