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[ CAS No. 2140-46-7 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2140-46-7
Chemical Structure| 2140-46-7
Structure of 2140-46-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2140-46-7 ]

CAS No. :2140-46-7 MDL No. :MFCD00057815
Formula : C27H46O2 Boiling Point : -
Linear Structure Formula :- InChI Key :INBGSXNNRGWLJU-ZHHJOTBYSA-N
M.W : 402.65 Pubchem ID :65094
Synonyms :
25-OHC

Calculated chemistry of [ 2140-46-7 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.93
Num. rotatable bonds : 5
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 124.81
TPSA : 40.46 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) : -3.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.55
Log Po/w (XLOGP3) : 6.78
Log Po/w (WLOGP) : 6.5
Log Po/w (MLOGP) : 5.41
Log Po/w (SILICOS-IT) : 5.64
Consensus Log Po/w : 5.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.28
Solubility : 0.000212 mg/ml ; 0.000000527 mol/l
Class : Poorly soluble
Log S (Ali) : -7.44
Solubility : 0.0000147 mg/ml ; 0.0000000366 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.19
Solubility : 0.00261 mg/ml ; 0.00000649 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 6.02

Safety of [ 2140-46-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335-H373 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2140-46-7 ]

* 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 [ 2140-46-7 ]

[ 2140-46-7 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 917-64-6 ]
  • [ 7494-34-0 ]
  • [ 2140-46-7 ]
  • 2
  • [ 917-64-6 ]
  • [ 7548-94-9 ]
  • [ 2140-46-7 ]
  • 3
  • [ 2140-46-7 ]
  • [ 19897-08-6 ]
YieldReaction ConditionsOperation in experiment
30% With aluminum tris(iso-propoxide); In acetone; toluene; for 6h;Reflux; A solution of 25HC (31 mg, 77 mumol) in toluene (3 mL) and acetone (3 mL) was treated with aluminium isopropoxide (78 mg, 0.382 mmol). The reaction mixture was refluxed for 6 h, then diluted with ethyl acetate and washed with aqueous HCl and brine. The organic layer was dried and concentrated,and the residue was purified by flash chromatography (hexane / ethyl acetate = 3:1) to afford the title compound (9.1 mg, 23 mumol, 30percent) as a pale yellow viscous solid.
  • 4
  • [ 917-64-6 ]
  • [ 23357-13-3 ]
  • [ 2140-46-7 ]
  • 6
  • [ 2140-46-7 ]
  • [ 5255-15-2 ]
  • 7
  • [ 59975-17-6 ]
  • [ 2140-46-7 ]
  • 8
  • [ 2140-46-7 ]
  • [ 108-24-7 ]
  • [ 2665-04-5 ]
  • 9
  • [ 2140-46-7 ]
  • [ 127619-25-4 ]
  • [ 127619-29-8 ]
  • 10
  • [ 2140-46-7 ]
  • [ 64164-45-0 ]
  • 11
  • [ 2140-46-7 ]
  • [ 51297-13-3 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; (a) 25-Hydroxycholesta-1,4,6-trien-3-one <strong>[2140-46-7]25-Hydroxycholesterol</strong> (3.4 gms) and dichlorodicyanoquinone (6.5 gms) dissolved in purified dioxan (100 mls) were heated at reflux for 20 hrs. The mixture was filtered and the solvent evaporated. Chromatography of the residue on alumina and elution with ethyl acetate and benzene afforded the trienone. Recrystallization from methanol gave the title compound, melting point 183°-184°. numax. 3600, 1650 and 1600 cm-1.
  • 12
  • 3β-hydroxy-cholene-(5)-carboxylic acid-(24)-ethyl ester [ No CAS ]
  • [ 917-54-4 ]
  • [ 2140-46-7 ]
  • 14
  • [ 7494-34-0 ]
  • [ 75-16-1 ]
  • [ 2140-46-7 ]
  • 15
  • [ 2140-46-7 ]
  • [ 108-24-7 ]
  • [ 10525-22-1 ]
YieldReaction ConditionsOperation in experiment
90% With dmap; triethylamine; In tetrahydrofuran; at 20℃; The compound 1 (3.66g, 9 . 08mmol) THF80mL of the solution, adding acetic anhydride (1.02g, 9 . 988mmol), triethylamine (1.84g, 18 . 16mmol) and DMAP (111 mg, 0 . 908mmol), stirring at room temperature, TLC monitoring, raw material the reaction is complete, to stop the stirring, by adding ethyl acetate after concentrating 50 ml, the organic phase washed 3 times, drying by anhydrous sodium sulfate, concentrated under vacuum, thick column chromatography (dichloromethane: methanol =40:1) to obtain the product 3.637g, yield 90percent.
  • 16
  • [ 55064-27-2 ]
  • [ 2140-46-7 ]
YieldReaction ConditionsOperation in experiment
140 mg With hydrogenchloride; In tetrahydrofuran; methanol; at 20℃; for 1h; Compound 6 (200 mg, 0.430 mmol) was dissolved in THF/water (5:1) (20 mL) and then the solution was cooled at ?5 °C under a nitrogen atmosphere. Then NBS (115.3 mg, 0.645 mmol) was slowly added in four batches over 1 h. The mixture was stirred at ?5 °C under a nitrogen atmosphere. After 2 h, the reaction was quenched with saturated Na2S2O4solution, washed with NaHCO3 (2 × 15 mL) and brine (2 × 15 mL), dried over anhydrous Na2SO4, and concentrated under reduced pressure to give the crude product. Purification by silica gel chromatography eluting with n-hexane/ethyl acetate (10:1) gave a white solid 7(218 mg, 90percent). The solid (220 mg, 0.39 mmol) was dissolved in THF (12 mL) and LiAlH4/THF (2.5 M, 0.624 mL, 1.6 mmol) was added dropwise at room temperature under a nitrogen atmosphere. The reaction mixture was refluxed at 70 °C for 3 h. The reaction was cooled to room temperature and concentrated under reduced pressure to give a crude product. This was dissolved in methanol/THF (2:1) (15 mL), HCl (36percent wt, 0.65 mL) was added dropwise, and the solution was then stirred for 1 h at room temperature. The mixture was extracted with CH2Cl2 (3 × 15 mL), washed with NaHCO3(2 × 15 mL) and brine (2 × 15 mL), and dried over anhydrous Na2SO4. The organic extract was concentrated under reduced pressure to give the crude product 8. Recrystallisation of the crude product from toluene gave the pure compound 8: White crystals; 140 mg (80percent); m.p. 191.5?193.4 °C (lit.3 185?187 °C); 1H NMR (600 MHz, CDCl3): delta5.37 (s, 1H), 3.56 (m, 1H), 2.30?1.24 (m, 22H), 1.23 (s, 6H), 1.21?1.05 (m, 5H), 1.02 (s, 3H), 0.96 (d, J = 6.5 Hz, 3H), 0.69 (s, 3H); 13C NMR (150 MHz, CDCl3): delta140.8, 121.7, 77.2, 77.0, 76.8, 71.8, 71.14, 56.7, 56.1, 44.4, 42.3, 42.3, 39.8, 37.3, 36.5, 36.5, 35.7, 31.9, 31.6, 29.3, 29.2, 28.3, 24.3, 21.1, 20.8, 19.4, 18.7, 18.4, 11.9; MS (ESI): C27H46NaO2 [M+Na]+; calculated: 425.3, found: 425.3.
  • 17
  • [ 55064-27-2 ]
  • [ 2140-46-7 ]
  • [ 53176-99-1 ]
  • 20
  • [ 80239-48-1 ]
  • [ 2140-46-7 ]
  • [ 51297-13-3 ]
  • 21
  • (23RS)-23-Phenylsulfonyl-5-cholesten-3β,25-diol [ No CAS ]
  • [ 2140-46-7 ]
  • 22
  • [ 917-64-6 ]
  • (R)-5-((3S,8S,9S,10R,13R,14S,17R)-3-Acetoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-hexanoic acid phenyl ester [ No CAS ]
  • [ 2140-46-7 ]
  • 24
  • [ 19897-08-6 ]
  • [ 2140-46-7 ]
  • 25
  • [ 75-16-1 ]
  • [ 23357-13-3 ]
  • [ 2140-46-7 ]
  • 26
  • [ 57-88-5 ]
  • [ 566-28-9 ]
  • [ 2140-46-7 ]
  • [ 566-27-8 ]
  • [ 1250-95-9 ]
  • 27
  • [ 2140-46-7 ]
  • 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl H-phosphonate triethylammonium salt [ No CAS ]
  • C41H65O13P [ No CAS ]
  • 28
  • [ 2140-46-7 ]
  • C12H19O10P*C6H15N [ No CAS ]
  • C39H63O11P [ No CAS ]
  • 29
  • [ 2140-46-7 ]
  • C26H37O20P*C6H15N [ No CAS ]
  • C53H81O21P [ No CAS ]
  • 30
  • [ 2140-46-7 ]
  • 2,3,4,6-tetra-acetyl-α-D-mannose-1-hydrogen phosphite monoester triethylamine Salt [ No CAS ]
  • C41H65O13P [ No CAS ]
  • 31
  • [ 2140-46-7 ]
  • C14H21O12P*C6H15N [ No CAS ]
  • C41H65O13P [ No CAS ]
  • 33
  • [ 2140-46-7 ]
  • ethanolic HClO4 [ No CAS ]
  • [ 70706-33-1 ]
  • 34
  • [ 2140-46-7 ]
  • [ 98-88-4 ]
  • [ 64164-61-0 ]
YieldReaction ConditionsOperation in experiment
79% With pyridine; In dichloromethane; at 20℃; for 42h;Inert atmosphere; To a solution of <strong>[2140-46-7]25-hydroxycholesterol</strong> (1, 100 mg, 24.8 mmol) in dichloromethane (3 mL) was added, pyridine (1 mL) followed by benzoyl chloride (100 mg, dissolved in 0.5 mL CH2Cl2) at room temperature. After stirring at room temperature for 42 h, the reaction was quenched with water (0.5 ml) and stirred for 1 h. Added water (5 mL) and transferred the contents to a separatory funnel and extracted with dichloromethane (2 x 25 mL). The organic layer was washed with 0.1N HCl (5 mL), water (5 mL), brine (5 mL) and dried over MgSO4. After filtration, the solvents were evaporated under reduced pressure. The residue thus obtained was purified by column chromatography using ethyl acetate-hexanes to yield the dibenzoate 2 as a white crystalline solid, 120 mg (79percent). Mp 101-102 °C (lit1. mp 100-103 °C). Spectroscopic data matched previously reported data.
In pyridine; dichloromethane hexane; acetone; A. 3beta,25-Dibenzoyloxycholest-5-ene Heat 2.9 gm. (7.2 mmole) of <strong>[2140-46-7]25-hydroxycholesterol</strong> with 2.1 ml. (18 mmole) of benzoyl chloride in 30 ml. of pyridine at 70°-80° C. for 4 hours. Add an additional 1.4 ml. (12 mmole) of benzoyl chloride and continue heating at 75°-80° C. for 1 hour. Pour the reaction mixture into ice-water mixture (b 1:1, 500 gm.) Stir for 1 hour, separate the precipitate and wash with ice-water. Recrystalize from acetone. Dissolve the crude product (3.8 gm.) in methylene chloride-hexane (3:2, 40 ml.) and pass the solution through a silica gel column (120 gm.). Elute the column with 800 ml. methylene chloride-hexane (5:1) followed by 800 ml. methylene chloridehexane (10:1). Combine the fractions and concentrate to a residue. Recrystalize from acetone to obtain the pure product (3.32 gm., m.p. 130°-132° C.).
  • 35
  • [ 77058-74-3 ]
  • [ 2140-46-7 ]
  • [ 474-73-7 ]
  • 37
  • [ 2140-46-7 ]
  • 5α-cholestane-3β,7α,25-triol [ No CAS ]
  • 38
  • [ 2140-46-7 ]
  • 5α-cholestane-3β,7β,25-triol [ No CAS ]
  • 40
  • [ 2140-46-7 ]
  • (3S,5R,7R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,7-diol [ No CAS ]
  • 41
  • [ 2140-46-7 ]
  • (3S,5R,7S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,7-diol [ No CAS ]
  • 42
  • [ 2140-46-7 ]
  • Acetic acid (3S,5R,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-5-trimethylsilanyloxy-hexyl)-10,13-dimethyl-7-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester [ No CAS ]
  • 44
  • [ 5255-17-4 ]
  • [ 2140-46-7 ]
  • 47
  • [ 66414-43-5 ]
  • [ 2140-46-7 ]
  • 49
  • [ 64727-04-4 ]
  • [ 2140-46-7 ]
  • 52
  • Acetic acid (3S,8S,9S,10R,13R,14S,17R)-17-((1R,4R)-5-hydroxy-4-methanesulfonyloxy-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester [ No CAS ]
  • [ 2140-46-7 ]
  • 56
  • [ 2140-46-7 ]
  • C39H63O12P [ No CAS ]
  • 57
  • [ 2140-46-7 ]
  • C41H65O14P [ No CAS ]
  • 58
  • [ 2140-46-7 ]
  • C41H65O14P [ No CAS ]
  • 59
  • [ 2140-46-7 ]
  • C41H65O14P [ No CAS ]
  • 60
  • [ 2140-46-7 ]
  • C53H81O22P [ No CAS ]
  • 65
  • [ 2140-46-7 ]
  • [ 51297-14-4 ]
  • 66
  • [ 2140-46-7 ]
  • 25-(1-Aethoxyaethoxy)-5-cholesten-1α,3β-diol [ No CAS ]
  • 68
  • [ 2140-46-7 ]
  • [ 75678-08-9 ]
  • 69
  • [ 2140-46-7 ]
  • [ 80239-46-9 ]
  • 72
  • [ 2140-46-7 ]
  • 5-Cholesten-1α,3α,25-triol [ No CAS ]
  • 76
  • [ 80239-47-0 ]
  • [ 2140-46-7 ]
  • 77
  • (23RS)-6β-Methoxy-23-phenylsulfonyl-25-<(tetrahydropyran-2yl)oxy>-3α,5-cyclo-5α-cholestan [ No CAS ]
  • [ 2140-46-7 ]
  • 78
  • [ 75303-37-6 ]
  • [ 2140-46-7 ]
  • 79
  • 27-nor-25,25-trimethylenedithio-3β-tetrahydropyranyloxy-5-cholestene [ No CAS ]
  • [ 2140-46-7 ]
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