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[ CAS No. 1493737-08-8 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1493737-08-8
Chemical Structure| 1493737-08-8
Chemical Structure| 1493737-08-8
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Product Details of [ 1493737-08-8 ]

CAS No. :1493737-08-8 MDL No. :MFCD21644405
Formula : C9H14N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ORIZOARFGLMZHN-UHFFFAOYSA-N
M.W : 198.22 Pubchem ID :73977812
Synonyms :

Calculated chemistry of [ 1493737-08-8 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.73
TPSA : 73.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : -0.15
Log Po/w (WLOGP) : 0.11
Log Po/w (MLOGP) : -0.38
Log Po/w (SILICOS-IT) : 0.02
Consensus Log Po/w : 0.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.78
Solubility : 33.2 mg/ml ; 0.167 mol/l
Class : Very soluble
Log S (Ali) : -0.94
Solubility : 22.7 mg/ml ; 0.115 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.45
Solubility : 70.2 mg/ml ; 0.354 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.4

Safety of [ 1493737-08-8 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1493737-08-8 ]

* 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 [ 1493737-08-8 ]

[ 1493737-08-8 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 398489-26-4 ]
  • [ 7677-24-9 ]
  • [ 1493737-08-8 ]
YieldReaction ConditionsOperation in experiment
With zinc(II) iodide In tetrahydrofuran at 20℃; for 24h; 18.1 Example 18; General Procedure for Synthesis of Alpha-hydroxy carboxylic acids; Step 1. O-(Trimethylsilyl) cyanohydrinesA 50-mL, one-necked flask equipped with a magnetic stirring bar and drying tube was charged with 10 mmol of ketone or aldehyde (such as N-Boc-3- Pyrrolidonone, N-Boc-3-Azetidinone, N-Boc-4-piperidone, N-Boc-3-azetidincarbox aldehyde, or tert-butyl-S-oxocyclobutylcarbamate), 1.39 g, 14 mmol of trimethylsilyl cyanide (Aldrich), 90 mg (0.28 mmol) of anhydrous zinc iodide, and 50 mL of dry THF. The solution was stirred at room temperature for 24 hours. The solvent was removed on a rotary evaporator; the residue was taken in 60 ml of EtAc. The organic layer was washed, sequentially, with 5% NaHCO3 (2 x 30 mL), H2O (1 x 30 mL), brine (1 x 30 mL) and dried over anhydrous Na2SO4. The solvent was evaporated off and the residue was used in the next step without purification.
  • 2
  • [ 1493737-08-8 ]
  • [ 24424-99-5 ]
  • [ 1035351-06-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C9H14N2O3 With hydrogenchloride; water; acetic acid for 2 - 3h; Heating / reflux; Stage #2: di-<i>tert</i>-butyl dicarbonate With sodium hydroxide In water; isopropyl alcohol at 20℃; for 4h; Stage #3: With phosphoric acid; water 18.2; 18.3 Step 2. Acid hydrolysis to α-hydroxy carboxylic acid; AcOH (25 ml) and cone. HCl (25 ml) were added to the unpurifed material from Step 1 and the reaction mixture was refluxed 2-3 hours. The reaction mixture was concentrated to dryness to give a white solid. The solid was used in the next step without purification.Step 3. Boc protection; 20 ml of 2 M NaOH solution and 20 ml of i-PrOH were added to the solid from Step 2. The flask was put in an ice-bath and BoC2O (6.6 g, 3 mmol) was added in several portions. The reaction mixture was then stirred for 4 hours at room temperature. After stirring at room temperature, i-PrOH was evaporated off, 50 ml of H2O was added, and the basic aqueous phase was extracted by Et2O (2 x 30 ml). After extraction with ether, the aqueous phase was made acidic (pH =3) by diluted H3PO4 and was extracted by EtOAc (2 x 60 ml). Organic phase was washed, sequentially H2O (2 x 30 mL), brine (1 x 30 niL) and dried over anhydrous Na2SO4. Organic phase was concentrated to give pure N-Boc-α-hydroxy carboxylic acids. Yields varied from 56- 72%.
  • 3
  • [ 1493737-08-8 ]
  • [ 1788041-57-5 ]
YieldReaction ConditionsOperation in experiment
With diethylamino-sulfur trifluoride In dichloromethane at 10℃; for 15.25h; 2 Synthesis of compound VIII: 1L single neck flask was added Intermediate (66.6g, 0.336mol, 1.0eq.), Dissolved with DCM (600mL), was added dropwise diethylamino sulfur trifluoride (81.2g, 0.504mol, 1.5eq.), at 10 °C , holding about 15min after dropping 10 °C reaction 15h, TLC the reaction was complete. The reaction solution was poured into 1L of stirring ice-water mixture, settled and separated, and the aqueous layer was washed with DCM (100mL × 1) and the combined DCM layers, then 1L of water, 1L saturated sodium bicarbonate, saturated sodium chloride, respectively 1L washed, the DCM layer was dried over anhydrous sodium sulfate, suction filtered, and concentrated to give 66.3 g light brown oil, sand column chromatography (PE ~ PE: EA = 10: 1) to give 59.3g pale yellow liquid, which solidified on standing theoretical yield: 67.27g, yield: 88.1%
  • 4
  • [ 398489-26-4 ]
  • [ 1493737-08-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 3 h / 60 °C 2: hydrogenchloride / ethyl acetate; lithium hydroxide monohydrate / 1 h / 0 °C
Multi-step reaction with 2 steps 1: zinc(II) iodide / tetrahydrofuran / 12 h / 25 °C 2: hydrogenchloride / ethyl acetate / 11 h / 0 °C
  • 5
  • [ 1067239-19-3 ]
  • [ 1493737-08-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In lithium hydroxide monohydrate; ethyl acetate at 0℃; for 1h; 6 Synthesis of compound VII: 500mL 4-neck flask was added Intermediate II (27.0g, 0 . 1mol, 1 . 0eq.), then adding ethyl acetate (200 ml) is dissolved, add 0.5N dilute hydrochloric acid aqueous solution (600 ml, 0 . 3mol, 3 . 0eq.), 0 °C insulation reaction 1h, TLC detection reaction is complete. Separating, EA for water (100 ml, 50 ml) extracting a time, respectively, combined with the phase, saturated aqueous sodium chloride solution (100 ml × 2) washing, dry anhydrous sodium sulfate, concentrated to obtain colorless oily 20.0g, cooling and turn into white solid, theoretical yield: 19.8g, crude yield: 100%.
With hydrogenchloride In ethyl acetate at 0℃; for 11h; 9.2 Step 2: Synthesis of Compound 9-3 At 0°C,To compound 9-2 (1 g, 3.70 mmol, 1 eq)ethyl acetate solution (10 mL) was addedDilute hydrochloric acid (0.5M, 11.09mL, 1.5eq),The reaction solution was stirred for 11 hours.The reaction solution was diluted with water (10 mL),Ethyl acetate (10mL×3) extraction,Combine the organic phases,The organic phase was washed with saturated brine (10 mL×2),dried over anhydrous sodium sulfate, filtered,The filtrate was concentrated under reduced pressure,The crude compound 9-3 was obtained.
  • 6
  • [ 1493737-08-8 ]
  • [ 329-59-9 ]
  • [ 2765502-90-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: tert-butyl 3-cyano-3-hydroxy-azetidine-1-carboxylate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: 4-Fluoro-3-nitrobenzenecarboxylic acid,methyl ester In N,N-dimethyl-formamide at 25℃; for 12h; 9.3 Step 3: Synthesis of Compounds 9-4 At 0°C,To a solution of compound 9-3 (0.1 g, 504.49 μmol, 1 eq) in N,N-dimethylformamide (2 mL) was addedsodium hydrogen (30.27 mg, 756.74 μmol, 60% pure, 1.5 eq),Stir for 30 minutes,Then compound 7-1 (100.46 mg, 504.49 μmol, 1 eq) was added thereto,The reaction solution was stirred at 25°C for 12 hours.The reaction solution was quenched by adding saturated ammonium chloride solution (10 mL),Ethyl acetate (10mL×3) extraction,Combine the organic phases,The organic phase was washed with saturated brine (10 mL×2),dried over anhydrous sodium sulfate, filtered,The filtrate was concentrated under reduced pressure,The crude product was separated and purified by silica gel column chromatography (petroleum ether:ethyl acetate=5:11:1)Compound 9-4 was obtained.
  • 7
  • [ 1493737-08-8 ]
  • [ 329-59-9 ]
  • [ 2765502-91-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 12 h / 25 °C 2.1: iron(0); ammonia hydrochloride / ethanol; lithium hydroxide monohydrate / 2 h / 75 °C
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