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[ CAS No. 612-61-3 ] {[proInfo.proName]}

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Chemical Structure| 612-61-3
Chemical Structure| 612-61-3
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Product Details of [ 612-61-3 ]

CAS No. :612-61-3 MDL No. :MFCD00956370
Formula : C9H6ClN Boiling Point : -
Linear Structure Formula :- InChI Key :QNGUPQRODVPRDC-UHFFFAOYSA-N
M.W : 163.60 Pubchem ID :521963
Synonyms :

Calculated chemistry of [ 612-61-3 ]      Expand+

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) : -5.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 2.42
Log Po/w (SILICOS-IT) : 3.13
Consensus Log Po/w : 2.67

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.39
Solubility : 0.0664 mg/ml ; 0.000406 mol/l
Class : Soluble
Log S (Ali) : -2.89
Solubility : 0.209 mg/ml ; 0.00128 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 : 1.22

Safety of [ 612-61-3 ]

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 [ 612-61-3 ]

* 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 [ 612-61-3 ]
  • Downstream synthetic route of [ 612-61-3 ]

[ 612-61-3 ] Synthesis Path-Upstream   1~29

  • 1
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YieldReaction ConditionsOperation in experiment
95% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 25℃; for 6 h; Inert atmosphere General procedure: PdCl2(dppf), PdCl2(tbpf) and (A.caPhos)PdCl2. A mixture of the halogenated heterocycle (0.66 mmol) in anhydrous THF (13.2 mL) was degassed by bubbling argon for few minutes. Then, PdCl2(dppf) (27.0 mg, 0.033 mmol, 5.0 molpercent), TMEDA (0.130 g, 1.12 mmol, 1.7 equiv) and finally NaBH4 (42.4 mg, 1.12 mmol, 1.7 equiv) were introduced in sequence. The mixture was stirred at room temperature under argon for the proper time and then worked up as described above.
65% at 20℃; for 5 h; General Procedure 138: 7-Chloroquinoline (Intermediate 573)4,7Dichloroquinoline (10 g, 50 mmol) in THF (100 ml) was degassed with N2 for 5 min. PdCl2dppf (1.2 g, 2 mmol), TMEDA (9.97 g, 86 mmol), and NaBH4 (3.24 g, 86 mmol) were added and the mixture was stirred at room temperature for 5 h. Brine (20 ml) was added dropwise and the solvent was removed in vacuo. The residue dissolved in EtOAc (200 ml), dried (MgSO4) and concentrated in vacuo. The crude residue was purified by column chromatography with heptane/EtOAC (4:1-1:1 gradient) as the eluent to give the title compound (5.4 g, 65percent).MW: 163.61HPLCMS (Method B):[m/z]: 163.90
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 12, p. 1562 - 1565
[2] Journal of Molecular Catalysis A: Chemical, 2014, vol. 393, p. 191 - 209
[3] Patent: US2012/214803, 2012, A1, . Location in patent: Page/Page column 185
  • 2
  • [ 98591-57-2 ]
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Reference: [1] Heterocycles, 2010, vol. 80, # 1, p. 601 - 606
[2] Tetrahedron Letters, 2008, vol. 49, # 9, p. 1492 - 1494
[3] Heterocycles, 2009, vol. 77, # 2, p. 1163 - 1170
[4] Heterocycles, 2011, vol. 83, # 4, p. 837 - 847
  • 3
  • [ 86-98-6 ]
  • [ 91-22-5 ]
  • [ 612-61-3 ]
  • [ 86-99-7 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 35, p. 4989 - 4993
[2] Tetrahedron Letters, 2010, vol. 51, # 12, p. 1562 - 1565
  • 4
  • [ 86-98-6 ]
  • [ 201230-82-2 ]
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  • [ 35714-48-8 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 19, p. 3719 - 3722
  • 5
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  • [ 201230-82-2 ]
  • [ 98-80-6 ]
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  • [ 145297-31-0 ]
  • [ 169957-11-3 ]
Reference: [1] Synlett, 2003, # 12, p. 1874 - 1876
  • 6
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  • [ 90562-35-9 ]
Reference: [1] Heterocycles, 2010, vol. 80, # 1, p. 601 - 606
  • 7
  • [ 108-42-9 ]
  • [ 504-63-2 ]
  • [ 612-61-3 ]
  • [ 635-27-8 ]
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2725 - 2727[2] Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 1993 - 1995,3
  • 8
  • [ 108-42-9 ]
  • [ 56-81-5 ]
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Reference: [1] RSC Advances, 2014, vol. 4, # 41, p. 21456 - 21464
  • 9
  • [ 1060737-02-1 ]
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  • [ 14548-50-6 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 5, p. 1281 - 1283
  • 10
  • [ 86-98-6 ]
  • [ 91-22-5 ]
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Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 35, p. 4989 - 4993
  • 11
  • [ 1203646-03-0 ]
  • [ 630-19-3 ]
  • [ 612-61-3 ]
  • [ 1310816-16-0 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 4, p. 837 - 847
  • 12
  • [ 108-42-9 ]
  • [ 504-63-2 ]
  • [ 612-61-3 ]
  • [ 31084-60-3 ]
Reference: [1] Organometallics, 2016, vol. 35, # 11, p. 1973 - 1977
  • 13
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Reference: [1] Heterocycles, 2011, vol. 83, # 4, p. 837 - 847
  • 14
  • [ 108-42-9 ]
  • [ 56-81-5 ]
  • [ 612-61-3 ]
  • [ 635-27-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 263
[2] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 283
[3] Chemische Berichte, 1885, vol. 18, p. 2941
[4] Chemische Berichte, 1884, vol. 17, p. 927
[5] Journal of the Chemical Society, 1947, p. 437,44
  • 15
  • [ 93626-92-7 ]
  • [ 1073-67-2 ]
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  • [ 28446-72-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1569 - 1572
  • 16
  • [ 1075-77-0 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1569 - 1572
  • 17
  • [ 1203646-03-0 ]
  • [ 612-61-3 ]
  • [ 791-28-6 ]
Reference: [1] Heterocycles, 2009, vol. 78, # 11, p. 2735 - 2739
  • 18
  • [ 98591-57-2 ]
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  • [ 1310816-16-0 ]
Reference: [1] Heterocycles, 2011, vol. 83, # 4, p. 837 - 847
  • 19
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  • [ 14548-50-6 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 5, p. 1281 - 1283
  • 20
  • [ 6828-35-9 ]
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  • [ 14548-50-6 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 5, p. 1281 - 1283
  • 21
  • [ 580-19-8 ]
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Reference: [1] Journal of the Chemical Society, 1947, p. 437,44
  • 22
  • [ 3820-67-5 ]
  • [ 612-61-3 ]
  • [ 71574-35-1 ]
Reference: [1] Pharmaceutical Sciences, 1997, vol. 3, # 2, p. 73 - 76
  • 23
  • [ 108-42-9 ]
  • [ 504-63-2 ]
  • [ 612-61-3 ]
  • [ 635-27-8 ]
Reference: [1] Russian Journal of General Chemistry, 2015, vol. 85, # 12, p. 2725 - 2727[2] Zh. Obshch. Khim., 2015, vol. 85, # 12, p. 1993 - 1995,3
  • 24
  • [ 108-42-9 ]
  • [ 56-81-5 ]
  • [ 612-61-3 ]
  • [ 635-27-8 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 263
[2] Journal fuer Praktische Chemie (Leipzig), 1893, vol. <2> 48, p. 283
[3] Chemische Berichte, 1885, vol. 18, p. 2941
[4] Chemische Berichte, 1884, vol. 17, p. 927
[5] Journal of the Chemical Society, 1947, p. 437,44
  • 25
  • [ 1060737-02-1 ]
  • [ 612-61-3 ]
  • [ 14548-50-6 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 5, p. 1281 - 1283
  • 26
  • [ 1375234-69-7 ]
  • [ 612-61-3 ]
  • [ 14548-50-6 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 5, p. 1281 - 1283
  • 27
  • [ 6828-35-9 ]
  • [ 612-61-3 ]
  • [ 14548-50-6 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 5, p. 1281 - 1283
  • 28
  • [ 612-61-3 ]
  • [ 90562-35-9 ]
YieldReaction ConditionsOperation in experiment
88% With iron(II) triflate; C13H21N3O2 In chloroform at 40℃; for 4 h; Schlenk technique General procedure: In a 10 mL Schlenk tube, Fe(OTf)2 (0.005 mmol, 1.8 mg), quinoline (0.5 mmol, 72 mg), Hantzsch ester A(1.25 mmol, 318 mg), and 1.0 mL CHCl3were added. The mixture was stirred at 40oCfor 2 h. The solution was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford the pure 1,2,3,4-tetrahydroquinoline (63.8 mg, 96percent yield).
69% With hydrogen In acetic acid at 20℃; for 4 h; Under hydrogen Preparation XLIX 9-Chloro-5,6-dihydro-4H-pyrrolo-[3,2,1-ij]quinoline [0348] 5-Chloro-1,2,3,4-tetrahydroquinoline [0349] A mixture of 5-chloroquinoline (10.0 g) and platinum oxide (50 mg) in acetic acid was shaken under a hydrogen atmosphere at room temperature for 4 hours. The mixture was diluted with diethyl ether and filtered through Celite. The volatiles were removed under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate (3.x.300 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified over silica gel and the fractions containing product were combined and concentrated under reduced pressure to provide 7.0 g (69percent) of the desired compound. [0350] MS (EI m/z) C9H10ClN (M+1) [0351] Ring Formation/Decarboxylation [0352] Beginning with 5-chloro-1,2,3,4-tetrahydroquinoline, the title compound was prepared essentially as described in Preparation I. [0353] MS (EI m/z) C11H10ClN (M+) 192.1 [0354] Analysis for C11H10ClN: [TABLE-US-00002] Calcd: C, 68.93; H 5.25; N, 7.30; Found: C, 69.18; H, 5.25; N, 6.97.
Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 12, p. 4417 - 4429
[2] Tetrahedron Letters, 2017, vol. 58, # 36, p. 3571 - 3573
[3] Patent: US2003/229026, 2003, A1, . Location in patent: Page 25
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Reference: [1] Heterocycles, 2010, vol. 80, # 1, p. 601 - 606
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