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[ CAS No. 2439-04-5 ] {[proInfo.proName]}

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Chemical Structure| 2439-04-5
Chemical Structure| 2439-04-5
Structure of 2439-04-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2439-04-5 ]

CAS No. :2439-04-5 MDL No. :MFCD00006906
Formula : C9H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 145.16 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 2439-04-5 ]

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 : 1.0
Molar Refractivity : 43.77
TPSA : 33.12 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) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 1.75
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 0.92
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.52
Solubility : 0.443 mg/ml ; 0.00305 mol/l
Class : Soluble
Log S (Ali) : -2.06
Solubility : 1.26 mg/ml ; 0.00866 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.115 mg/ml ; 0.000791 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 2439-04-5 ]

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 [ 2439-04-5 ]

* 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 [ 2439-04-5 ]
  • Downstream synthetic route of [ 2439-04-5 ]

[ 2439-04-5 ] Synthesis Path-Upstream   1~25

  • 1
  • [ 27655-40-9 ]
  • [ 2439-04-5 ]
YieldReaction ConditionsOperation in experiment
16 g With sodium hydroxide In water for 24 h; Reflux 23 g of 5-sulfonic acid isoquinoline was added to 400 ml of water, 60 g of NaOH was added, and the mixture was heated under reflux and stirred for 24 hours.Cool to room temperature, adjust the pH to 5 with dilute hydrochloric acid, add ethyl acetate for extraction, collect the organic phase, and concentrate.The residue was separated on a silica gel column to give 16 g of 5-hydroxyisoquinoline.
Reference: [1] Acta Poloniae Pharmaceutica, 1994, vol. 51, # 6, p. 479 - 482
[2] Patent: CN107778231, 2018, A, . Location in patent: Paragraph 0023; 0024
  • 2
  • [ 1125-60-6 ]
  • [ 2439-04-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2> 52, p. 10
[2] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2> 52, p. 10
[3] Yakugaku Zasshi, 1953, vol. 73, p. 666[4] Chem.Abstr., 1954, p. 7014
  • 3
  • [ 119-65-3 ]
  • [ 112259-27-5 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1987, p. 1722 - 1724
  • 4
  • [ 139484-28-9 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 5
  • [ 36556-06-6 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 6
  • [ 24334-24-5 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 7
  • [ 50388-20-0 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 8
  • [ 139484-26-7 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 9
  • [ 97112-03-3 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 10
  • [ 139484-27-8 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 11
  • [ 139484-24-5 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 12
  • [ 139484-25-6 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 1, p. 31 - 35
  • 13
  • [ 119-65-3 ]
  • [ 2439-04-5 ]
Reference: [1] Patent: CN107778231, 2018, A,
  • 14
  • [ 1532-72-5 ]
  • [ 2439-04-5 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 666[2] Chem.Abstr., 1954, p. 7014
[3] Yakugaku Zasshi, 1953, vol. 73, p. 666[4] Chem.Abstr., 1954, p. 7014
[5] Yakugaku Zasshi, 1953, vol. 73, p. 666[6] Chem.Abstr., 1954, p. 7014
  • 15
  • [ 57554-78-6 ]
  • [ 2439-04-5 ]
Reference: [1] Yakugaku Zasshi, 1953, vol. 73, p. 666[2] Chem.Abstr., 1954, p. 7014
[3] Yakugaku Zasshi, 1953, vol. 73, p. 666[4] Chem.Abstr., 1954, p. 7014
[5] Yakugaku Zasshi, 1953, vol. 73, p. 666[6] Chem.Abstr., 1954, p. 7014
  • 16
  • [ 607-32-9 ]
  • [ 2439-04-5 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1895, vol. <2> 52, p. 10
  • 17
  • [ 119-65-3 ]
  • [ 3482-14-2 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 9, p. 1065 - 1072
  • 18
  • [ 119-65-3 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 9, p. 1065 - 1072
  • 19
  • [ 7664-93-9 ]
  • [ 143247-61-4 ]
  • [ 7651-83-4 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 860,869
  • 20
  • [ 119-65-3 ]
  • [ 136918-14-4 ]
  • [ 491-30-5 ]
  • [ 2439-04-5 ]
  • [ 643-79-8 ]
Reference: [1] Journal of Physical Chemistry A, 1998, vol. 102, # 34, p. 6760 - 6765
  • 21
  • [ 7664-93-9 ]
  • [ 143247-61-4 ]
  • [ 7651-83-4 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the American Chemical Society, 1945, vol. 67, p. 860,869
  • 22
  • [ 119-65-3 ]
  • [ 3482-14-2 ]
  • [ 2439-04-5 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1993, # 9, p. 1065 - 1072
  • 23
  • [ 2439-04-5 ]
  • [ 14097-42-8 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 426
[2] Bulletin de la Societe Chimique de France, 1961, p. 272
  • 24
  • [ 24424-99-5 ]
  • [ 2439-04-5 ]
  • [ 216064-48-1 ]
YieldReaction ConditionsOperation in experiment
58% With hydrogenchloride; acetic acid In tetrahydrofuran; sodium hydroxide (1)
Platinum oxide (100 mg) was added to an acetic acid (30 ml) solution of 5-hydroxyisoquinoline (2.9 g, 20 mmols), and this was hydrogenated at room temperature under atmospheric pressure.
After the reaction, the catalyst was removed through filtration, and the filtrate was concentrated under reduced pressure.
The residue was crystallized from toluene(20 ml) and taken out through filtration.
The resulting crystal was dissolved in a mixture of aqueous 1 N sodium hydroxide solution (40 ml) and tetrahydrofuran (40 ml), to which was added di-tert-butyl dicarbonate (4.8 g, 22 mmols).
The reaction mixture was stirred at room temperature for 1 hour, to which was added 1 N hydrochloric acid (40 ml).
This was extracted with diethyl ether.
The extract was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure.
The crystal precipitated was recrystallized from diisopropyl ether to give a colorless crystal of 2-tert-butoxycarbonyl-5-hydroxy-tetrahydroisoquinoline (2.9 g, 58 percent).
m.p. 163-164°C
1H-NMR (CDCl3) 6: 1.49(9H,s), 2.76(2H,t,J=6.0Hz),
42%
Stage #1: With platinum(IV) oxide; hydrogen In ethanol for 48 h;
Stage #2: With triethylamine In tetrahydrofuran; water at 20℃; for 16 h;
The solution of 34 (1.0 g,90percent purity, 6.2 mmol) in AcOH (20 mL) were hydrogenated over Pt02 (85 mg) at 1 atmosphere for 48 h, filtered through Celite and concentrated in vacuo. The residue was dissolved in acetone (3 mL), and diluted with ethyl ether (3 mL). The precipitate was collected and dried in vacuo. The crude product (700 mg, 4.7 mmol) was suspended in THF/water (10 mL/2 mL). Boc2O (1.1 g, 5.0 mmol) and triethylamine (1.5 mL, 10 mmol) were added. The mixture was stirred at room temperature for 16 h, partitionedbetween ethyl acetate (50) ml and water (50 mL). The organic phase was washed with brine, dried over magnesium sulphate and concentrated in vacuo. The crude product was purified by flash chromatography eluting with 30percent ethyl acetate-petrol ether to give a white solid (490 mg, 42percent yield). mp 156-158 °C; ‘H NMR (400 MHz, CDC13) 57.03 (d, J = 7.8 Hz, 1H, ArH), 6.68 (d, J = 7.9 Hz, 1H, ArH), 6.63 (d, J = 7.8 Hz, 1H, ArH), 4.55 (s, 2H, CH2), 3 .65 (t, J= 6.1 Hz, 2H, CH2), 2.75 (t, J= 6.0 Hz, 2H, CH2) and 1.48 (s,9H); HRMS (ESI) calcd. for C,4H,9NNaO3 (M+Na) 272.1263, found 272.1244.
Reference: [1] Patent: EP1123918, 2001, A1,
[2] Patent: WO2016/108045, 2016, A2, . Location in patent: Page/Page column 29
  • 25
  • [ 2439-04-5 ]
  • [ 216064-48-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 24, p. 6293 - 6297
[2] Tetrahedron, 2006, vol. 62, # 29, p. 6869 - 6875
[3] Patent: WO2014/100730, 2014, A1,
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