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[ CAS No. 2157-52-0 ] {[proInfo.proName]}

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Chemical Structure| 2157-52-0
Chemical Structure| 2157-52-0
Structure of 2157-52-0 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 2157-52-0 ]

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Product Citations

Product Details of [ 2157-52-0 ]

CAS No. :2157-52-0 MDL No. :MFCD00016356
Formula : C13H9NO Boiling Point : No data available
Linear Structure Formula :- InChI Key :CRNNFEKVPRFZKJ-UHFFFAOYSA-N
M.W : 195.22 Pubchem ID :16543
Synonyms :

Calculated chemistry of [ 2157-52-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 59.3
TPSA : 32.59 ?2

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) : -4.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 3.84
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 2.49
Log Po/w (SILICOS-IT) : 3.33
Consensus Log Po/w : 2.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.06
Solubility : 0.0169 mg/ml ; 0.0000868 mol/l
Class : Moderately soluble
Log S (Ali) : -4.22
Solubility : 0.0118 mg/ml ; 0.0000602 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.65
Solubility : 0.00439 mg/ml ; 0.0000225 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 3.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.39

Safety of [ 2157-52-0 ]

Signal Word:Danger Class:4.1,6.1
Precautionary Statements:P240-P210-P241-P280-P370+P378-P501-P261-P270-P271-P264-P337+P313-P305+P351+P338-P361+P364-P332+P313-P301+P310+P330-P302+P352+P312-P304+P340+P311-P403+P233-P405 UN#:2926
Hazard Statements:H228-H301+H311+H331-H315-H319 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2157-52-0 ]

* 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.

  • Downstream synthetic route of [ 2157-52-0 ]

[ 2157-52-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 2157-52-0 ]
  • [ 525-03-1 ]
YieldReaction ConditionsOperation in experiment
With acetic acid; zinc; In water; at 110℃; for 1h; To a 110 C stirred solution of 9H-fluoren-9-one oxime (26a, 3.0 g) in 50 mL of glacial acetic acid (47.5 mL) and water (2.5 ml) was added zinc dust (6.0 g) in small portions. After 1 h, the solution was filtered, concentrated. The residue was treated with 5 N HCl (60 mL), and then the mixture was allowed to cool to 0 C. After 10 h of stirring, the mixture was filtered, to give 9-fluorenone-oxime hydrochloride, which was basified with ammonia, the amine being finally crystallized from light petroleum as white solid: mp 60-61 C (lit.4 61-63C); 1H-NMR (400 MHz, CDCl3) δ: 4.91 (s, 1H), 7.32 (t, 2H), 7.45 (t, 2H), 7.71 (d, 2H), 7.79 (d, 2H); EI-MS m/z 180.1 (M+, 100%).
  • 2
  • [ 2157-52-0 ]
  • [ 5978-75-6 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; under 760.051 Torr; First step, 9-fluorenone oxime (400 mg) and concentrated HCl (0.86 ml) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (33 mg). The reaction solution was filtered and the filtrate was concentrated. The residue was suspended in EtOAc, and the suspension was filtered to yield fluorenamine hydrochloride (240 mg) as a white solid. Second step, a mixture of fluorenamine (304 mg, the hydrochloride), 6-chloropurine riboside (200 mg) and triethylamine (3 ml) in PrOH (60ml) was heated to 70C and reacted for 8 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (20 : 1) to yield N6-(fluorene-9-yl)-adenosine(208 mg) as a white solid: positive ESIMS m/z 432 [M + H]+ and 454 [M + Na]+; negative ESIMS m/z 430 [M - H]- and 466 [M + Cl]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.46. (1H, d, J = 8.1 Hz, -NH), 8.38 (2H, s, H-2, H-8), 5.94 (1H, d, J = 5.4 Hz, H-1), 5.52 (1H, d, J = 5.7 Hz, -OH), 5.44 (1H, m, -OH), 5.25 (1H, d, J = 4.8 Hz, -OH), 4.66 (1H, m, H-2'), 4.19 (1H, m, H-3'), 4.01 (1H, m, H-4'), 3.67 (1H, m, H-5'a), 3.56 (1H, m, H-5'b); the 9-fluorene moiety delta 7.86 (2H, d, J = 7.5 Hz, H-4", H-5"), 7.46 (2H, d, J = 7.5 Hz, H-1, H-8), 7.40 (2H, t, J= 7.5 Hz, H-2", H-7"), 7.26 (2H, t, J= 7.5 Hz, H-3", H-6), 6.69 (1H, d, J = 8.1 Hz, H-9"); 13C NMR (75 MHz, DMSO-d6): the adenosine moiety delta 155.1 (s, C-6), 152.4 (d, C-2), 148.8 (s, C-4), 140.3 (d, C-8), 120.2 (s, C-5), 88.1 (d, C-1), 86.0 (d, C-4'), 73.6 (d, C-2'), 70.7 (d, C-3'), 61.7 (t, C-5'); the 9-fluorene moiety delta 145.0 (s, C-8"a, C-9"a), 140.3 (s, C-4"a, C-5a ), 128.3 (d, C-1, C-8"), 127.5 (d, C-3", C-6"), 124.8 (d, C-2", C-7"), 120.2 (d, C-4", C-5"), 54.9 (d, C-9")o
240 mg With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr; First step, 9-fluorenone oxime (400 mg) and concentrated HCl (0.86 ml) in EtOH (50 ml) was subjected to hydrogenation at atmospheric pressure in the presence of 10% Pd/C (33 mg). The reaction solution was filtered and the filtrate was concentrated. The residue was suspended in EtOAc, and the suspension was filtered to yield fluorenamine hydrochloride (240 mg) as a white solid.
240 mg With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In ethanol; water; weigh precisely 9-fluorenone oxime (400 mg) and add 10% Pd / C (33 mg) and concentrated hydrochloric acid (0.86 mL), dissolved in EtOH (50 mL), hydrogenated under atmospheric pressure , Filter the reaction solution, remove Pd / C, evaporate the filtrate, add ethyl acetate, mix well,Dissolve, filter to give pale yellow solid 9-fluorene hydrochloride (240 mg)
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Technical Information

? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stille Coupling ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction
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