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[ CAS No. 52602-39-8 ] {[proInfo.proName]}

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Chemical Structure| 52602-39-8
Chemical Structure| 52602-39-8
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Quality Control of [ 52602-39-8 ]

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Product Details of [ 52602-39-8 ]

CAS No. :52602-39-8 MDL No. :MFCD02178385
Formula : C12H9NO Boiling Point : No data available
Linear Structure Formula :- InChI Key :UEOHATPGKDSULR-UHFFFAOYSA-N
M.W : 183.21 Pubchem ID :104251
Synonyms :

Calculated chemistry of [ 52602-39-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 13
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.83
TPSA : 36.02 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.69
Log Po/w (XLOGP3) : 3.51
Log Po/w (WLOGP) : 3.03
Log Po/w (MLOGP) : 2.17
Log Po/w (SILICOS-IT) : 3.09
Consensus Log Po/w : 2.7

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.87
Solubility : 0.0245 mg/ml ; 0.000134 mol/l
Class : Soluble
Log S (Ali) : -3.95
Solubility : 0.0206 mg/ml ; 0.000112 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.38
Solubility : 0.00757 mg/ml ; 0.0000413 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.34

Safety of [ 52602-39-8 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 52602-39-8 ]

* 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.

  • Downstream synthetic route of [ 52602-39-8 ]

[ 52602-39-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 52602-39-8 ]
  • [ 3132-64-7 ]
  • [ 51997-51-4 ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydroxide; In dimethyl sulfoxide; at 60℃; for 24h; 1a (897 mg, 6.55 mmol) and NaOH (222 mg, 5.55 mmol) solu-tion were added to a solution of 4-hydroxycarbazole (1000 mg,5.55 mmol) in DMSO. The reaction mixture was stirred for 24 h at60C. It was then cooled to 20C, diluted with 25 mL of water and extracted with ethyl acetate three times (3 20 mL). The collectedorganic layers were washed with brine, dried with Na2SO4 andconcentrated. The residue was puried by ash chromatography onsilica-gel with 20% ethyl acetate in hexane. Yielding 60% of com-pound 5a (798 mg) as a white solid. Compound 5b was synthesizedfollowing the procedure of preparation 4a.
  • 2
  • [ 52602-39-8 ]
  • [ 152333-94-3 ]
  • [ 51997-51-4 ]
  • 3
  • [ 52602-39-8 ]
  • [ 106-89-8 ]
  • [ 51997-51-4 ]
YieldReaction ConditionsOperation in experiment
80.4% 200.Og (1.09 mole) of 4- hydroxy carbazole is dissolved in 500.0 ml of isopropyl alcohol. To this solution is added dropwise an aqueous solution of sodium hydroxide made from 48 g (1.2 moles) of sodium hydroxide dissolved in 700.0 ml of water. The addition of alkali solution is done by maintaining the temperature at 23 to 28 C. After the addition of entire quantity of sodium hydroxide solution, the reaction mixture is stirred for 1 hour at the same temperature of 23 to 28 C. To this solution 236 g (2.55 moles) of epichlorhydrin is added all at once. The reaction mixture is then stirred at room temperature (30-40C) for 15-20 hours. During this period the reaction mixture is monitored by thin layer chromatography (TLC), till the reaction showed complete utilization of 4-hydroxy carbazole. 4- (2,3-epoxypropoxy) thus formed, precipitated from the reaction mixture, which is filtered and the cake is washed with 150ml of water and 150 ml of isopropyl alcohol. The product is dried at 50-55 C for 4-5 hours. Yield: 210.0 g. (80.4%) M. P. 133 c 1H NMR (200 MHZ, in CDCl3) 8 (ppm) 8.1 (bs, 1H, exchanges with d20), 6.8-8.3 (m 7H), 4.4-4.2 (m, 2H), 3.5 (m, 1H), 2.8-3 (m, 2H)
76.57% EXAMPLE I; Preparation of 4-(2,3-epoxypropoxy) carbazole; To lOOg of 4-hydroxy carbazole (II) in dimethyl sulfoxide (250ml.) at 10-30C, IN aq. NaOH solution (545ml.) is added and the reaction mixture is stirred at 10-30C for 15-20 minutes. Epichlorohydrin (80g) is added at 10-30C over a period of 30-45 minutes and the resultant reaction mixture is stirred at 20-250C for 25-30 hr.The progress of reaction is monitored by TLC/HPLC. After completion of reaction, the solid, thus precipitated out, was filtered followed by washing with water (300ml). The wet cake was dissolved in ethyl acetate (300ml) at 60-65. The resulting solution is cooled to 0-50C and stirred for lhr. The solid, thus obtained, was filtered and washed with chilled ethyl acetate (10ml). The product was dried at 40-450C for 6-8 hr until moisture content is <1.0%.(10Og; 76.57%); HPLC purity > 99.6?%
70% With sodium hydroxide; In ethanol; water; at 20℃; for 21h; To a 1000 mL three-necked flask with mechanical stirring was added ethanol (300 mL), water (300 mL) and sodium hydroxide(13.2 g, 0.33 mol) was stirred and dissolved, then cooled to room temperature,4-hydroxycarbazole (54.96 g, 0.3 mol) was added and stirred for 60 minutes,Epichlorohydrin (30.53 g, 0.33 mol) was added and the reaction was stirred at room temperature for 20 hours.Filtered, washed with 50% ethanol / water (100 ml)Dried to give 4- (2,3-epoxypropyloxy) -carbazole (50.24 g) as a tan solid in 70% yield, with purity greater than 96% by HPLC.
65% With potassium carbonate; In acetonitrile; for 24h;Reflux; The 4 - hydroxy-carbazole (1g, 5.5mmol) for 20 ml acetonitrile dissolved, add catalyst potassium carbonate (1.52g, 11mmol) and epichlorohydrin (5.0 ml, 6 . 4mmol), heating reflux reaction to the raw reaction is complete, the reaction time is about 24h. Evaporate the solvent under reduced pressure, the residue for 50 ml ethyl acetate to dissolve the, water washing 3 times, each 20 ml. The organic layer is separated, and 20 ml saturated salt water washing 1 time, then adding anhydrous sodium sulfate drying, reducing pressure and solvent, it is crude. Purification of the crude product by column chromatography (dichloromethane: petroleum ether=1:1), to obtain a white solid product (0.86g, 65%).
65% With potassium carbonate; In acetonitrile; for 24h;Reflux; To a suspension of 4-hydroxy carbazole (1 g, 5.5 mmol) andK2CO3 (1.52 g, 11 mmol) in acetonitrile (20 mL), epichlorohydrin(5.0 mL, 6.4 mmol) was added. The reactionmixture was refluxed for 24 h. After completion of thereaction, as indicated by TLC, the acetonitrile in the reactionmixture was removed under reduced pressure. Theobtained residue was dissolved in ethyl acetate (50 mL),organic phase was washed with water (3 × 20 mL), separated,dried with anhydrous Na2SO4, evaporated underreduced pressure, and purified by column chromatographyover silica gel (1:1, dichloromethane/petroleum ether) togive 1 as a white solid (0.86 g, 65%). 1H NMR (400 MHz,CDCl3) delta 8.36 (d, J = 7.9, 0.9 Hz, 1H), 8.10 (s, 1H),7.46-7.39 (m, 2H), 7.35 (t, J = 8.0 Hz, 1H), 7.27 (dd, J =5.8, 2.2 Hz, 1H), 4.49 (dd, J = 11.0, 3.3 Hz, 1H), 4.30 (dd,J = 11.0, 5.4 Hz, 1H), 3.59 (dddd, J = 5.6, 4.1, 3.4, 2.6 Hz,1H), 3.03 (dd, J = 5.0, 4.1 Hz, 1H), 2.92 (dd, J = 5.0, 2.6Hz, 1H). 13C NMR (100 MHz, CDCl3) delta 155.02, 141.01,138.76, 126.62, 125.14, 123.24, 122.55, 119.78, 112.92,110.00, 104.09, 101.39, 68.84, 50.40, 44.92. MS ESI:239.1.
64% With sodium hydroxide;tetrabutylammomium bromide; In water; at 30℃; for 2 - 3h; Step 2: Preparation of 2,3-Epoxypropoxy carbazole; 4-Hydroxy carbazole (60g) obtained in step 1 was charged into a reactor containing water (90ml). Epichlorohydrin (64.2g) and tetrabutyl ammonium bromide (6.3g) were then charged into the reactor under stirring. 50% Sodium hydroxide solution (78g) was added slowly in 2 - 3 hours into the reaction mass at about 30C. After completion of reaction, ethyl acetate (315ml) and potable water (315ml) were charged into the reaction mass. The lower aqueous layer was separated and discarded. The ethyl acetate layer was washed with potable water to obtain neutral pH and dried over anhydrous sodium sulphate. The ethyl acetate is distilled out under vacuum below 55C to about 100ml. The reaction mass was chilled to 0- 5C and filtered and dried at 50-60C to give the title compound (50g) (64%).
64% With potassium carbonate; In acetone; for 24h;Reflux; To a suspension of 4-hydroxy carbazole (5 g, 0.027 mol) and K2CO3 (7.54 g, 0.054 mol) in acetone (80 mL), epichlorohydrin (2.50 mL, 0.032 mol) was added. The reaction mixture was refluxed for 24 h. After completion of the reaction, as indicated by TLC, the acetone in the reaction mixture was removed under reduced pressure. The obtained residue was dissolved in ethyl acetate (75 mL), organic phase was washed with water (3 x 15 mL), separated, dried with Na2SO4, evaporated under reduced pressure and purified by column chromatography over silica gel (25:75, ethyl acetate/hexane) to afford 8 as solid compound. Yield 64%; mp 167-169 C; 1H NMR (300 MHz, CDCl3): delta 2.81-2.88 (dd, J = 2.45, 2.64 Hz, 1Ha, CH2), 2.90-2.97 (dd, J = 4.34, 4.91 Hz, 1Hb, CH2), 3.50-3.57 (m, 1Hc, CH), 4.04-4.14 (dd, J = 6.23 Hz, 1He, CH2), 4.52-4.59 (dd, J = 2.26 Hz, 1Hd, CH2), 6.70 (d, J = 7.93 Hz, 1H, Ar-H), 7.05-7.20 (m, 2H, Ar-H), 7.25-7.39 (m, 2H, Ar-H), 7.46 (d, J = 7.93 Hz, 1H, Ar-H), 8.17 (d, J = 7.14 Hz, 1H, Ar-H), 11.27 (s, 1H, NH); ESI MS: m/z = 239 [M+].
9.8 g (72%) With sodium hydroxide; In water; dimethyl sulfoxide; Example 14 4-Oxiranylmethoxy-9H-carbazole 10.4 g of 4-hydroxy-carbazole (57 mmol) were dissolved in 31.1 ml of DMSO. 6.9 ml of epichlorohydrin (88 mmol) were added and next 57 ml of a 1 N sodium hydroxide solution. The mixture was stirred for 8 h at 40 C. It was cooled to 20 C. adn 130 ml of water were added. The product was filtered under suction, and washed with 3*30 ml water. The crude material was recrystallized from isopropanol. The substance was dried at 60 C. for 12 h. Yield: 9.8 g (72%), m.p. 128-132 C.
With potassium carbonate; In ipa; at 75 - 85℃; for 6h; IPA (70ml) was added to a mixture of 4-etaydroxy carbazole (0.05458 moles, 10 g) and epichlorohydrin (0.10916 moles, 8.5 ml). Potassium carbonate (0.13645 moles, 18.85 g) was added to the above reaction mixture and stirred. Subsequently the reaction mixture was heated to 75-85 0C. After 6 hours when the reaction was complete, the reaction mixture was slowly cooled to room temperature and filtered. The filtrate was reduced to 80% of its volume, and stirred at room temperature, when a solid was formed which was filtered to give the product.
With potassium carbonate; In isopropyl alcohol; at 75 - 85℃; for 6h; Step 1: Preparation of 4-(Oxiran-2-ylmethoxy)-9H-carbazole IPA (70 ml) was added to a mixture of 4-Hydroxy carbazole (0.05458 moles, 10 g) and epichlorohydrin (0.10916 moles, 8.5 ml). Potassium carbonate (0.13645 moles, 18.85 g) was added to the above reaction mixture and stirred. Subsequently the reaction mixture was heated to 75-85 C. After 6 hours when the reaction was complete, the reaction mixture was slowly cooled to room temperature and filtered. The filtrate was reduced to 80% of its volume, and stirred at room temperature, when a solid was formed which was filtered to give the product.
General procedure: Commercially unavailable 2-(aryloxymethyl)oxiranes were synthesized by following procedure as previously reported. To a solution of corresponding phenols in dimethyl sulfoxide (DMSO) at room temperature,NaOH aqueous solution (1 M, 1.2 equiv) was added, the volume ratio of solvent is DMSO:H2O = 2:1, the mixture was stirred for10 min and epichlorohydrin (1.5 equiv) was added dropwise within10 min, the reaction mixture was allowed to stirred for further 2 h.AcOEt was added to the mixture, which was washed by brine for 3times. The solvents were evaporated under vacuum, and the crude residuewas purified by column chromatography on silica gel.

  • 4
  • active charcoal [ No CAS ]
  • R-(-)-epichlorhydrin [ No CAS ]
  • [ 52602-39-8 ]
  • [ 50-59-9 ]
  • [ 67-68-5 ]
  • [ 51997-51-4 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In dichloromethane; water; ethyl acetate; EXAMPLE 3 S-(+)-4-(2,3-Epoxypropoxy)-carbazole 27.5 g. 4-Hydroxycarbazole are dissolved in a mixture of 150 ml. 1N aqueous sodium hydroxide solution and 70 ml. dimethyl sulphoxide. To this is added at ambient temperature 13.9 g. R-(-)-epichlorhydrin, followed by stirring for 18 hours at ambient temperature. 280 ml. Water are then added thereto, followed by stirring for 15 minutes and filtering off with suction. The filter residue is washed with 0.1N aqueous sodium hydroxide solution and water and subsequently dissolved in methylene chloride. The methylene chloride solution is dried over anhydrous sodium sulphate, treated with active charcoal and floridin and evaporated. The residue is purified by recrystallising twice from ethyl acetate. Yield: 15.2 g. S-(+)-4-(2,3-epoxypropoxy)-carbazole; m.p.: 163-164 C.; [alpha]D20: +64.4 (c=1; pyridine). From the mother liquors, there are isolated a further 6.7 g. of product; m.p.: 163-164 C.; [alpha]D20: +64.5 (c=1, pyridine).
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