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[ CAS No. 1181770-72-8 ] {[proInfo.proName]}

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Chemical Structure| 1181770-72-8
Chemical Structure| 1181770-72-8
Structure of 1181770-72-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1181770-72-8 ]

CAS No. :1181770-72-8 MDL No. :MFCD25541743
Formula : C18H18F2N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :SSNAPUUWBPZGOY-UHFFFAOYSA-N
M.W : 364.34 Pubchem ID :44182398
Synonyms :
Chemical Name :N'-(2-(3,5-difluorophenyl)-2-hydroxyacetyl)-2-ethyl-4-hydroxy-3-methylbenzohydrazide

Calculated chemistry of [ 1181770-72-8 ]

Physicochemical Properties

Num. heavy atoms : 26
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.22
Num. rotatable bonds : 7
Num. H-bond acceptors : 6.0
Num. H-bond donors : 4.0
Molar Refractivity : 89.57
TPSA : 98.66 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.18
Log Po/w (XLOGP3) : 2.76
Log Po/w (WLOGP) : 2.55
Log Po/w (MLOGP) : 2.8
Log Po/w (SILICOS-IT) : 3.12
Consensus Log Po/w : 2.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.72
Solubility : 0.0699 mg/ml ; 0.000192 mol/l
Class : Soluble
Log S (Ali) : -4.49
Solubility : 0.0119 mg/ml ; 0.0000326 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.5
Solubility : 0.00115 mg/ml ; 0.00000315 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.27

Safety of [ 1181770-72-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1181770-72-8 ]

* 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 [ 1181770-72-8 ]

[ 1181770-72-8 ] Synthesis Path-Downstream   1~8

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  • [ 38998-17-3 ]
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  • [ 5628-61-5 ]
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  • [ 1181770-72-8 ]
  • [ 1184940-47-3 ]
  • [ 1184940-46-2 ]
YieldReaction ConditionsOperation in experiment
With Chiralpak AD column; In n-heptane; isopropyl alcohol;Resolution of racemate; Ia. N'-[(S)-2-(3,5-Difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-hydroxy-3-methylbenzohydrazidea) Chromatographic Racemate Separation (No Fig.):500 mg of Example 1 (<strong>[1181770-72-8]EMD 638683</strong>) are dissolved in 4 portions in 5 ml of 2-propanol and 5 ml of n-heptane in each case at elevated temperature. The solutions are subsequently chromatographed on 2 serial Chiralpak AD (5×20 cm) chromatography columns (Daicel) with the solvent mixture n-heptane/12-propanol (4:1, parts by volume; 0.8 ml/min) (retention time: 6.11 min). The combined product fractions are evaporated to dryness in vacuo, giving 245 mg of the title compound in analytically and enantiomerically pure form as colourless solid having a melting point of 202.3 C. MS: 365 (M+Fr), 382 (M+NH4+); TLC: Rf=0.29 (cyclohexane/methyl tert-butyl ether 1:4, parts by volume); [alpha]20D=+30.4 (c=0.0201 g/2 ml of methanol).; Ib. N'-[(R)-2-(3,5-Difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-hydroxy-3-methylbenzohydrazidea) Chromatographic Racemate Separation (No Fig.):500 mg of Example 1 (<strong>[1181770-72-8]EMD 638683</strong>) are dissolved in 4 portions in 5 ml of 2-propanol and 5 ml of n-heptane in each case at elevated temperature. The solutions are subsequently chromatographed on 2 serial Chiralpak AD (5×20 cm) chromatography columns (Daicel) with the solvent mixture n-heptane/2-propanol (4:1, parts by volume; 0.8 ml/min) (retention time: 9.36 min). The combined product fractions are evaporated to dryness in vacuo, giving 250 mg of the title compound as colourless solid having a melting point of 203.7 C. MS: 365 (M+H+); TLC: Rf=0.29 (cyclohexane/methyl tert-butyl ether 1:4, parts by volume); [alpha]20D=-29.7 (c=0.0184 g/2 ml of methanol), enantiomeric excess 98.2%.
  • 6
  • [ 1181770-80-8 ]
  • [ 1181770-72-8 ]
YieldReaction ConditionsOperation in experiment
48% With boron tribromide; In dichloromethane; at 20.0℃; for 3.0h; I. N'-[2-(3,5-Difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-hydroxy-3-methylbenzohydrazide (EMD 638683) 70.0 g of N'-[2-(3,5-difluorophenyl)-2-hydroxyacetyl]-2-ethyl-4-methoxy-3-methylbenzohydrazide (A1) are suspended in 350 ml of dichloromethane. 105 ml of boron tribromide are then added dropwise. The reaction mixture is stirred at room temperature for 3 hours. The resultant solution is subsequently carefully decanted into one litre of ice-water. The aqueous phase is extracted twice with 500 ml of ethyl acetate. The combined organic phases are then extracted once with 300 ml of water, dried over sodium sulfate and subsequently filtered. The filtrate is concentrated in vacuo. The resultant residue is, then recrystallised from 500 ml of acetonitrile using activated carbon, giving 32.2 g of the title compound as colourless solid having a melting point of 187.4 C. (MS: 365 (MH+), TLC: Rf=0.29 (cyclohexane/methyl tert-butyl ether 1:4, parts by volume).
  • 7
  • 3,5-difluorophenylhydroxyacetohydrazide [ No CAS ]
  • [ 1181770-72-8 ]
  • 8
  • [ 1181770-76-2 ]
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