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[ CAS No. 13104-56-8 ] {[proInfo.proName]}

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Chemical Structure| 13104-56-8
Chemical Structure| 13104-56-8
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Product Details of [ 13104-56-8 ]

CAS No. :13104-56-8 MDL No. :MFCD06796987
Formula : C22H17N3O Boiling Point : -
Linear Structure Formula :- InChI Key :QAEWAYWLMREGRA-UHFFFAOYSA-N
M.W : 339.39 Pubchem ID :630929
Synonyms :

Calculated chemistry of [ 13104-56-8 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.05
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 102.63
TPSA : 47.9 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.59
Log Po/w (XLOGP3) : 3.56
Log Po/w (WLOGP) : 4.88
Log Po/w (MLOGP) : 2.0
Log Po/w (SILICOS-IT) : 4.99
Consensus Log Po/w : 3.8

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.61
Solubility : 0.00841 mg/ml ; 0.0000248 mol/l
Class : Moderately soluble
Log S (Ali) : -4.25
Solubility : 0.019 mg/ml ; 0.0000561 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.93
Solubility : 0.000000402 mg/ml ; 0.0000000012 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.58

Safety of [ 13104-56-8 ]

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 [ 13104-56-8 ]

* 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 [ 13104-56-8 ]
  • Downstream synthetic route of [ 13104-56-8 ]

[ 13104-56-8 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
45.62%
Stage #1: With potassium hydroxide In ethanol at 20℃; for 0.166667 h;
Stage #2: With ammonium hydroxide In ethanol at 37℃; for 24 h;
General procedure: Synthesis of 4′-(3-methoxyphenyl)-2,2′:6′,2″-terpyridine (3-MeO-Phtpy), 4′-(2-methoxyphenyl)-2,2′:6′,2″-terpyridine (2-MeO-Phtpy) and 4′-(4-methoxyphenyl)-2,2′:6′,2″-terpyridine (4-MeO-Phtpy) were performed using the methods described previously [27–33]. 2-Acetylpyridine (2.813g, 23.2mmol, 2 eq.) was added to 2-methoxybenzaldehyde, 3-methoxybenzaldehyde or 4-methoxybenzaldehyde (11.6mmol, 1 eq.) dissolved in 50mL ethanol. KOH pellets (46.5mmol, 4 eq.) were added to this solution. The reaction mixture was stirred at room temperature for 10min. NH3 (40mL, 25percent aq.) was slowly added to the reaction mixture. After a 24-h incubation at 37°C, 5mL of 25percent aq. NH3 was added to the reaction mixture again. The flask containing the reaction mixture was cooled to−20°C. The obtained white precipitate in the flask was isolated through filtration and washed with cold ethanol. We further purified the each product using recrystallization in ethanol-H2O. After recrystallization, each product was recovered by filtration, washed with cold ethanol and petroleum ether, and dried under high vacuum for 24h (Scheme 1).
37% With ammonium hydroxide; potassium hydroxide In ethanol at 20℃; for 24 h; General procedure: Ketone (20 mmol) (2-acetylpyridine, 2-acetylthiazole or 2-acetylpyrazine)was added to a solution of aldehyde (10 mmol) (4-methoxybenzaldehyde,4-methoxy-1-naphthaldehyde or 6-methoxy-2-naphthaldehyde) in EtOH (75 mL). KOH (1.54 g, 27.5 mmol) and NH3(aq)(35 mL) were then added. The solution was stirred at room temp. for 24 h. The solid was collected by filtration and washed with H2O. Recrystallization from ethanol (L1,L4, L7) or toluene (L2, L3, L5, L6, L8,L9) afforded a crystalline solid. 4′-(4-methoxy-1-phenyl)-2,2′:6′,2″-terpyridine (L1): Yield: 37percent. IR(KBr, cm−1): 1588(s), 1467(m), 1389(m), 1204(m), 1157(m),1069(m), 790(m), 739(m) and 655(m). NMR: 1H NMR (400 MHz,CDCl3) δ 8.73 (d, J=4.1 Hz, 2H, HA1), 8.71 (s, 2H, HB2), 8.67 (d,J=7.9 Hz, 2H, HA4), 7.90–7.85 (m, 4H, HC2+A3), 7.37–7.33 (m, 2H,HA2), 7.03 (d, J=8.7 Hz, 2H, HC3), 3.88 (s, 3H, HC5). 13C NMR(100 MHz, CDCl3) δ 160.66, 156.55, 155.99, 149.90, 149.24, 136.96,130.92, 128.67, 123.87, 121.49, 118.42, 114.46, 55.52. C22H17N3O(339.39 g mol−1): calcd C, 77.86; H, 5.05; N, 12.38percent; found: C, 77.46;H, 5.35; N, 12.25percent. DSC: (I run) Tm=164 °C; (II run) Tg=30, Tc=82and Tm=163 °C.
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[6] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 1387 - 1395
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[13] Journal of the Chemical Society. Perkin Transactions 2, 2001, # 7, p. 1045 - 1050
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[16] Journal of Organic Chemistry, 2011, vol. 76, # 6, p. 1910 - 1913
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[18] Polyhedron, 2012, vol. 40, # 1, p. 159 - 167
[19] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 104, p. 48 - 55
[20] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2014, vol. 117, p. 662 - 668
[21] Journal of Inorganic Biochemistry, 2014, vol. 141, p. 17 - 27
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Reference: [1] Organic Letters, 2016, vol. 18, # 21, p. 5640 - 5643
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Reference: [1] Synthesis, 2006, # 17, p. 2873 - 2878
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Reference: [1] Synthesis, 2006, # 17, p. 2873 - 2878
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  • [ 60-35-5 ]
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Reference: [1] Helvetica Chimica Acta, 1984, vol. 67, # 54, p. 450 - 454
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  • [ 26482-00-8 ]
  • [ 18451-44-0 ]
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Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 1996, vol. 7, p. 1275 - 1282
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