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[ CAS No. 4698-11-7 ] {[proInfo.proName]}

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Chemical Structure| 4698-11-7
Chemical Structure| 4698-11-7
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Quality Control of [ 4698-11-7 ]

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Product Details of [ 4698-11-7 ]

CAS No. :4698-11-7 MDL No. :MFCD00101079
Formula : C15H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :ZKHZWXLOSIGIGZ-UHFFFAOYSA-N
M.W : 223.27 Pubchem ID :78424
Synonyms :

Calculated chemistry of [ 4698-11-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 73.74
TPSA : 21.26 ?2

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 : Yes
Log Kp (skin permeation) : -5.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.55
Log Po/w (XLOGP3) : 3.65
Log Po/w (WLOGP) : 3.4
Log Po/w (MLOGP) : 2.73
Log Po/w (SILICOS-IT) : 3.08
Consensus Log Po/w : 3.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.98
Solubility : 0.0234 mg/ml ; 0.000105 mol/l
Class : Soluble
Log S (Ali) : -3.79
Solubility : 0.0366 mg/ml ; 0.000164 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.4
Solubility : 0.000883 mg/ml ; 0.00000395 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.96

Safety of [ 4698-11-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4698-11-7 ]

* 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.

  • Downstream synthetic route of [ 4698-11-7 ]

[ 4698-11-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 4698-11-7 ]
  • [ 917-61-3 ]
  • [ 28721-09-7 ]
YieldReaction ConditionsOperation in experiment
50% [10-METHOXY-5H-DIBENZ (B, 0AZEPINE] (29.9 g, 0.134 mol) was added to 300 ml acetonitrile in a three-neck flask (500 ml) equipped with a mechanical stirring apparatus. The mixture was stirred at room temperature for 15 minutes, and then [NAOCN] (18 g, 0.277 mol) was added, followed by pyridiniump-toluenesulfonate (75 g, 0.3 mol). The mixture was stirred at room temperature for about 4 hours, at which time TLC indicated that the reaction was complete (disappearance of [10-METHOXY-5H-DIBENZ (BAZEPINE).] 30 ml water was added, and the mixture stirred for 15 minutes. The solids were filtered and the filtrate was concentrated under vacuum. The semi-solid residue was triturated with acetone to provide a creamy solid, which was dried at [80] C to provide 18 g (0.068 mol, 50% yield) of [10-METHOXY-5H-DIBENZ [B2FLAZEPINE-5-CARBOXAMIDE (10-METHOXYCARBAMAZEPINE).]
In a three-neck flask (500 ml), equipped with a mechanical stirring apparatus, 15 ml water was introduced, followed by pyridinium bromide (71.75 g, 0.45 mole; Chemadaa' (Nir Yitshak, Israel) ). The mixture was stirred at room temperature [(22 C)] for about 10 minutes. Then 250 ml toluene was added, followed by 50 g (0.224 mol) of [10-METHOXY-5H-] dibenz [[BZF] AZEPINE] (compound of formula (4), wherein R4 is methoxy). [Note: 10-methoxy-5H- dibenz [[B, T] AZEPINE] may be obtained from [IMINOSTILBENE] according to the process disclosed in U. S. Patent No. 5,808, 058. [10-METHOXY-5H-DIBENZ [B FLAZEPINE] also is commercially available from various suppliers, including Zhejiang Jiuzhou Pharmaceutical Co. , Ltd. (Zhejiang, China), and Ningbo Chongyangtang Biologic Tech Co. , Ltd. (Ningbo, China)] [NAOCN] (45 g, 0.69 mol ; OCI Corp. , South Korea) was added and the reaction was mixed for about 7-8 hours at room temperature [(22C).] After [7-8] hours, [125ML] of water was added, and the mixture was stirred for about 15 minutes. The resulting solid carbamate of formula (1), 10-methoxy-5H- dibenz [[B2TAZEPINE-5-CARBOXAMIDE,] was filtered and washed with 50 ml of water. The organic layer was separated and washed with water (2 x [50ML).] In a 500 ml three necked flask, the organic phase from above was introduced, to which the solid carbamate of formula (1) [(10-METHOXY-5H-DIBENZ [B2FLAZEPINE-5-CARBOXAMIDE)] was added to form a slurry. The mixture was heated to 89 C to clarify the solution, and 250 ml of 10% [HC1] was added dropwise with stirring. When thin layer chromatography indicated that the intermediate carbamate of formula (1) had been substantially consumed, the reaction mixture was cooled to room temperature and the mixture was stirred at this temperature for 15-30 minutes. The product, [10-OXO-10,] [11-DIHYDRO-5H-DIBENZ [B2FLAZEPINE-5-CARBOXAMIDE] (oxcarbazepine), was filtered and the crude oxcarbazepine cake was thoroughly washed with water until the pH reached 6-7. The mixture was then washed with toluene (50 ml), and the solids were dried to yield 34.4 g (0.137 mol) crude oxcarbazepine as a yellow-brown powder (yield relative to (2) is [61%).] The crude oxcarbazepine was slurried in 408 ml of boiling 80: 20 isopropanol : water for about 1 hour. The solid was separated by filtration and dried to afford 30.6 g oxcarbazepine [(89%] purification yield). Further purification was carried out in 765 ml of boiling 80: 20 isopropanol: water, hot filtration and cooling to room temperature. Filtration and drying of the solid precipitate afforded 26.5 g of purified oxcarbazepine (yield relative to starting material (2) is 47%, and purification yield is 87%).; The carbamoylation reaction was performed as in Example 1, except that [150] ml toluene was used instead of 250 ml. The resulting solid carbamate of formula (1), 10-methoxy-5H- dibenz [[B2FLAZEPINE-5-CARBOXAMIDE,] was isolated as described in Example 1. In a three necked flask, 330 ml of isopropyl alcohol, 78 ml of 12% HCl, and the solid 10- [METHOXY-SH-DIBENZ [B2FLAZEPINE-S-CARBOXAMIDE] were introduced. The mixture was heated to [78] [- 82 C] for about 1 hour. When TLC indicated that the carbamate of formula (1) was consumed, the reaction mixture was cooled to room temperature and stirred for 1 hour. The separated solids were filtered and washed with water to provide crude 10-oxo-10, [11-DIHYDRO-SH-DIBENZ [BFLAZEPINE-S-] carboxamide (oxcarbazepine), which was purified as described in Example 1. Yield relative to starting material of formula (2) was 43-45%.
With maleic acid; In dichloromethane; at 20 - 45℃; for 6 - 24h; EXAMPLE 1A Preparation of 10-methoxycarbamazepine To a 1 L 4-necked round bottom flask was added 10.0 g (0.045 mol) of 10-methoxyiminostilbene, 150.0 ml of dichloromethane, 37.0 g (0.57 mol) of sodium cyanate and 15.0 g (0.13 moles) of maleic acid and stirred at room temperature. The contents were heated to reflux (40-45 C.) under vigorous stirring for about 6 to about 8 hours. After completion of the reaction (detected by TLC) the reaction mass was filtered and washed with 50.0 ml dichloromethane. The dichloromethane layer was washed with water (50.0 ml*2) and the layers were separated. EXAMPLE 2A Preparation of 10-methoxycarbamazepine 50.0 g (0.224 moles) of 10-methoxyiminostilbene was dissolved in 750.0 ml of dichloromethane. 185.0 g (2.846 moles) of sodium cyanate and 75.0 g (0.65 moles) of maleic acid were added to the above solution at a temperature ranging from about 25 C. to about 30 C. The reaction mass was stirred for about 24 hours. After completion of the reaction (determined by HPLC/TLC) the reaction mass was filtered and washed three times with 100 mL of dichloromethane. The dichloromethane layer was evaporated to get a residue of about 150 g to about 200 g.
With MANDELIC ACID; In dichloromethane;Reflux;Product distribution / selectivity; EXAMPLE-2: Preparation of Oxcarbazepine; a) Preparation of 10-methoxy carbamazepine from 10-methoxyiminostilbene; A suspension of 10 g of 10-methoxyiminostilbene in 250 ml dichloromethane was -30 treated with 17.5 g of sodium cyanate and 24 g of mandelic acid and was heated to reflux for about 6-8 hrs. The reaction mixture was cooled to room temperature and the reaction mixture was washed with distilled water and aqueous sodium bicarbonate and further the organic layer was distilled off completely. The resulting residue was treated with with isopropanol, separated solid was filtered and dried to give g of35 10-methoxy carbamazepine.
Example 5; Preparation of 10-oxo-lOJ l-dihydro-5H-dibenz[6,/]azepine-5-carboxamide (Oxcarbazepine), compound of formula [I]; 10-Methoxyiminostilbene, compound of formula [XX], (100 g) was dissolved in toluene (1000 ml). Sodium cyanate (100 g) and benzoic acid (190 g) were added and the reaction mixture was vigorously stirred and heated at 85-90C for 1O h. After the reaction completion, the reaction mixture was cooled, followed by the addition of aqueous NaOH solution (10%, 800 ml) to pH 11. The reaction mixture was stirred for 3 h at this temperature followed by cooling to 0-50C. The reaction mixture was filtered and washed with toluene and water and dried to give the compound of formula [XXI] (yield = 110 g).
With MANDELIC ACID; In dichloromethane; at 20℃; for 8h;Reflux;Product distribution / selectivity; a) Preparation of 10-methoxy carbamazepine from 10-methoxyiminostilbene A suspension of 10 g of 10-methoxyiminostilbene in 250 ml dichloromethane was treated with 17.5 g of sodium cyanate and 24 g of mandelic acid and was heated to reflux for about 6-8 hrs. The reaction mixture was cooled to room temperature and the reaction mixture was washed with distilled water and aqueous sodium bicarbonate and further the organic layer was distilled off completely. The resulting residue was treated with with isopropanol, separated solid was filtered and dried to give g of 10-methoxy carbamazepine.

  • 2
  • [ 76041-86-6 ]
  • [ 4698-11-7 ]
  • 3
  • [ 590-28-3 ]
  • [ 4698-11-7 ]
  • [ 28721-09-7 ]
  • 4
  • [ 4698-11-7 ]
  • [ 32315-10-9 ]
  • [ 28721-09-7 ]
YieldReaction ConditionsOperation in experiment
85% ) A solution of 66.9 g (0.3 mols) of 10-methoxy-iminostilbene and 34.92 g (0.34 mols) of triethylamine in 800 ml of toluene is gradually added, during 6 hours and at a temperature of 10-15C, with a solution of 32.67 g (0.11 mols) of triphosgene in 300 ml of toluene. After completion of the reaction (disappearance of methoxy-iminostilbene) 200 ml of 30% aqueous ammonia are added gradually, vigorously stirring at room temperature for some hours. After that, the phases are separated, the toluene phase is washed with water and evaporated to dryness under reduced pressure. Yield: 69.0 g (85% on theoretical) of 10-methoxy-N-aminocarbonyl-iminostilbene (V) of purity higher than 95%.
  • 5
  • [ 4698-11-7 ]
  • [ 232951-82-5 ]
  • [ 28721-09-7 ]
YieldReaction ConditionsOperation in experiment
80% To a solution of 10-methoxy-5H-dibenz[b,f]azepine (3; 223.3 mg, 1.0 mmol) in CH2Cl2 (5 mL) at r.t. under argon was added FmocNCO (397.9 mg, 1.5 mmol). The mixture was stirred for 16 h, then piperidine (2.5 mL, 25.2 mmol) and MeOH (13 mL) were added successively. After the removal of MeOH, the residue was extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo, and the residue was purified by silica gel column chromatography (EtOAc-hexane, 1:2) to give 8 as a white solid; yield: 213 mg (0.800 mmol, 80%); mp 193-194 C. IR (ATR): 3476, 1666, 1600, 1402, 1133 cm-1. 1H NMR (600 MHz, CDCl3): delta = 7.73 (d, J = 7.3 Hz, 1 H), 7.45 (m, 3 H), 7.35 (m, 1 H), 7.27 (m, 3 H), 6.14 (s, 1 H), 5.20-4.10 (br, 2 H), 3.88 (s, 3H). 13C NMR (150 MHz, CDCl3): delta = 156.8, 156.0, 140.1, 138.5, 135.0, 134.6, 133.0, 130.4, 129.2, 128.2, 128.1, 127.7, 127.6, 127.5, 127.3, 55.4. HRMS (ESI): m/z [M + H]+ calcd for C16H14N2O2: 267.1128; found: 267.1123.
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