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[ CAS No. 1468-95-7 ] {[proInfo.proName]}

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Chemical Structure| 1468-95-7
Chemical Structure| 1468-95-7
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Product Details of [ 1468-95-7 ]

CAS No. :1468-95-7 MDL No. :MFCD00001264
Formula : C15H12O Boiling Point : -
Linear Structure Formula :- InChI Key :JCJNNHDZTLRSGN-UHFFFAOYSA-N
M.W : 208.26 Pubchem ID :73848
Synonyms :

Calculated chemistry of [ 1468-95-7 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.07
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 67.58
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.41 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 3.04
Log Po/w (WLOGP) : 3.33
Log Po/w (MLOGP) : 3.44
Log Po/w (SILICOS-IT) : 3.9
Consensus Log Po/w : 3.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.63
Solubility : 0.0491 mg/ml ; 0.000236 mol/l
Class : Soluble
Log S (Ali) : -3.13
Solubility : 0.154 mg/ml ; 0.00074 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.58
Solubility : 0.000543 mg/ml ; 0.00000261 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 1468-95-7 ]

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 [ 1468-95-7 ]

* 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 [ 1468-95-7 ]
  • Downstream synthetic route of [ 1468-95-7 ]

[ 1468-95-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 1468-95-7 ]
  • [ 24463-19-2 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 30, p. 10409 - 10432
[2] Bulletin of the Chemical Society of Japan, 2000, vol. 73, # 1, p. 97 - 105
[3] Tetrahedron, 1996, vol. 52, # 47, p. 14929 - 14936
[4] Carbohydrate Research, 2011, vol. 346, # 1, p. 35 - 42
[5] Helvetica Chimica Acta, 1955, vol. 38, p. 2009,2020
[6] Journal of Medicinal Chemistry, 1965, vol. 8, p. 342 - 347
[7] Australian Journal of Chemistry, 1960, vol. 13, p. 478 - 487
[8] Journal of Organic Chemistry, 1980, vol. 45, # 8, p. 1497 - 1505
[9] European Journal of Organic Chemistry, 2007, # 6, p. 1013 - 1017
[10] Journal of Medicinal Chemistry, 2007, vol. 50, # 26, p. 6465 - 6475
[11] Tetrahedron, 2008, vol. 64, # 47, p. 10735 - 10740
[12] Beilstein Journal of Organic Chemistry, 2010, vol. 6,
[13] Angewandte Chemie - International Edition, 2018, vol. 57, # 9, p. 2469 - 2473[14] Angew. Chem., 2018, vol. 130, p. 2494 - 2498,5
  • 2
  • [ 1468-95-7 ]
  • [ 2417-77-8 ]
YieldReaction ConditionsOperation in experiment
87% With phosphorus tribromide; potassium hydrogencarbonate In toluene at 0 - 20℃; for 5 h; Inert atmosphere 9-Bromomethylanthracene was prepared in good yield (>87percent) by the reduction of 9-anthracenecarboxaldehyde, followed by bromination with PBr3 under N2 atmosphere in toluene. To a stirred solution of 9-bromomethylanthracene (0.1g, 0.37mmol) in ACN (10mL), diethanolamine (0.07g, 0.67mmol), anhydrous K2CO3 (0.07g, 0.50mmol), and KI (0.08g, 0.50mmol) were added under N2. The reaction mixture was refluxed for 12h. The work-up was similar to that of PD. The crude product was purified using silica-gel chromatography (elution with 8.0percent MeOH in CH2Cl2:EtOAc (7:3 v/vpercent) containing 1.4percent NH4OH, Rf=0.5), yielding a brownish semi-solid PM (0.10g, 91percent).
69% With bromine; triphenylphosphine In acetonitrile at 20℃; for 2 h; A solution of triphenylphosphine (16.44 g, 100.8 mmol) in acetonitrile (120 mL) was flushed with nitrogen for 20 minutes. Bromine (3.3 mL) was added and a solution of anthracen-9-yl-methanol (15.0 g, 72.0 mmol) in acetonitrile (10O mL) was added dropwise. The mixture was stirred for 2 hours at room temperature and refrigerated at 50C overnight. The solution was cooled to 00C for 30 minutes and filtered. The residue was washed with cold acetonitrile and purified by recrystallization from chloroform to give 9-bromomethyl-anthracene as yellow crystals (13.47 g, 69percent yield). 1H NMR (CDCl3) δ 8.51 (IH, s), 8.32 (2H, d), 8.05 (2H, d), 7.66 (2H, dd), 7.52 (2H, dd), 5.56 (2H, s).
54% With phosphorus tribromide In toluene at 0 - 20℃; for 2 h; 7-(anthracen-9-ylmethoxy)-4-methyl-2H-chromen-2-one (48) SU06-02; 9-(bromomethyl)anthracene (47); To a stirring suspension of 9-anthracenemethanol (2.0 g, 9.6 mmol) at 0 0C in toluene (100 ml) was added PBr3 (1.2 ml_, 12.51 mmol) and the suspension was stirred at 0 °C for 1 h. The reaction mixture was then brought up to room temperature and let to stir for further 1 h. The mixture turned into a yellow solution. K2CO3 (10 mL) was added to quench the reaction. Toluene was evaporated off in-vacuo. The residue was taken up in EtOAc and washed with saturated aqueous K2CO3, water and brine and dried (MgSO4). The solvent was evaporated off in-vacuo and the crude residue was purified by flash chromatography, eluting with hexane:EtOAc (2:1 ) to give 47 (1.4 g, 54percent) as yellow solid. H1 NMR (500MHz, CDCI3): δ = 8.45 (1 H, s, Ar-10 H), 8.27 (2H, d, Ar-1 ,8 H), 8.00 (2H, d, Ar-4, 6 H), 7.62 (2H, d, Ar-2, 7 H), 7.48 (2H, d, Ar-3, H), 5.50 (2H, s, CH2).
Reference: [1] Tetrahedron, 2005, vol. 61, # 23, p. 5699 - 5704
[2] RSC Advances, 2016, vol. 6, # 5, p. 3783 - 3791
[3] Journal of Organic Chemistry, 2003, vol. 68, # 25, p. 9678 - 9686
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 18, p. 6496 - 6504
[5] Angewandte Chemie - International Edition, 2016, vol. 55, # 8, p. 2719 - 2723[6] Angew. Chem., 2016, vol. 55-128, # 8, p. 2769 - 2773,5
[7] Organic Letters, 2018, vol. 20, # 4, p. 1046 - 1049
[8] Journal of Organometallic Chemistry, 2006, vol. 691, # 7, p. 1389 - 1401
[9] Inorganica Chimica Acta, 2018, vol. 482, p. 669 - 680
[10] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 21, p. 2995 - 2996
[11] Polish Journal of Chemistry, 1999, vol. 73, # 10, p. 1725 - 1732
[12] Organic Letters, 2002, vol. 4, # 25, p. 4487 - 4490
[13] Organic Letters, 2005, vol. 7, # 14, p. 2809 - 2812
[14] Patent: WO2008/91670, 2008, A2, . Location in patent: Page/Page column 45
[15] Patent: WO2010/125350, 2010, A1, . Location in patent: Page/Page column 57
[16] Chemistry - A European Journal, 2002, vol. 8, # 24, p. 5630 - 5643
[17] Bol. Inst. Quim. Univ. Mexico, 1956, vol. 8, p. 10,15
[18] Journal of medicinal chemistry, 1972, vol. 15, # 1, p. 68 - 70
[19] Bulletin of the Chemical Society of Japan, 1971, vol. 44, p. 2231 - 2236
[20] Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1976, vol. 357, # 1, p. 7 - 19
[21] Journal of Physical Chemistry B, 1999, vol. 103, # 43, p. 9366 - 9377
[22] Chemical Communications, 2005, # 4, p. 513 - 515
[23] Chemical Communications, 2008, # 35, p. 4180 - 4182
[24] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 115, p. 26 - 32
[25] RSC Advances, 2014, vol. 4, # 62, p. 33062 - 33073
[26] European Journal of Organic Chemistry, 2015, vol. 2015, # 30, p. 6631 - 6640
[27] Macromolecules, 2016, vol. 49, # 10, p. 3845 - 3855
[28] Chemical Communications, 2016, vol. 52, # 83, p. 12330 - 12333
  • 3
  • [ 779-02-2 ]
  • [ 1468-95-7 ]
  • [ 23674-17-1 ]
  • [ 2417-77-8 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 10, p. 3005 - 3009
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