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Structure of 2591-76-6

Chemical Structure| 2591-76-6

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Product Details of [ 2591-76-6 ]

CAS No. :2591-76-6
Formula : C9H19NO
M.W : 157.25
SMILES Code : CC(C)CN(CC(C)C)C=O
MDL No. :MFCD00042942
InChI Key :NTYICSDTCGMBQM-UHFFFAOYSA-N
Pubchem ID :75770

Safety of [ 2591-76-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 2591-76-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 0
Fraction Csp3 0.89
Num. rotatable bonds 5
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 48.86
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

20.31 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.39
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.4
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.76
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.28
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.4
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.04

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.0
Solubility 1.58 mg/ml ; 0.0101 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.47
Solubility 0.535 mg/ml ; 0.0034 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.61
Solubility 3.89 mg/ml ; 0.0247 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.56 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.0

Application In Synthesis of [ 2591-76-6 ]

* 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 [ 2591-76-6 ]

[ 2591-76-6 ] Synthesis Path-Downstream   1~21

  • 1
  • [ 64-18-6 ]
  • [ 110-96-3 ]
  • [ 2591-76-6 ]
YieldReaction ConditionsOperation in experiment
743 g With water; at 160 - 200℃; under 12751.3 Torr; for 3.66667h;Autoclave; 227.3 g of formic acid having a purity of 85% (ie, 34.1 g of water) and 522.2 g of diisobutylamine having a purity of 99% were added to a 1-liter autoclave,The stirrer was started to mix well and a homogeneous reaction system was obtained. The molar ratio of formic acid to diisobutylamine was 1.05:1.While maintaining the stirring, the homogeneous reaction system was heated to 160 C. and kept warm for about 40 minutes.Continuing to heat up to about 200C, the pressure in the autoclave rises to about 1.7 MPa and does not continue to rise. The reaction is maintained for about 3 hours, and the carbon monoxide and water vapor in the autoclave are vented and the reaction product is collected to obtain about 743g uniform transparent solution.
  • 2
  • [ 110-96-3 ]
  • [ 67-66-3 ]
  • [ 2591-76-6 ]
  • 3
  • [ 693-03-8 ]
  • [ 2591-76-6 ]
  • [ 42298-81-7 ]
  • 4
  • [ 2591-76-6 ]
  • [ 77-78-1 ]
  • [ 50746-36-6 ]
  • 5
  • [ 908094-01-9 ]
  • [ 2591-76-6 ]
  • copper (II) deuteroprophyrin IX dimethyl ester [ No CAS ]
  • [ 15295-15-5 ]
  • [ 15295-21-3 ]
  • [ 15295-20-2 ]
  • [ 15295-14-4 ]
  • 6
  • [ 52459-75-3 ]
  • [ 2591-76-6 ]
  • [ 52459-77-5 ]
  • [ 52459-79-7 ]
  • [ 87206-77-7 ]
  • 8
  • [ 2591-76-6 ]
  • [ 121211-58-3 ]
  • [ 121211-59-4 ]
  • [ 79491-23-9 ]
  • 9
  • [ 110-96-3 ]
  • [ 33513-42-7 ]
  • [ 2591-76-6 ]
  • 11
  • [ 110-96-3 ]
  • carbon monoxide [ No CAS ]
  • [ 2591-76-6 ]
  • 12
  • [ 2591-76-6 ]
  • [ 68714-13-6 ]
  • 13
  • [ 570416-08-9 ]
  • [ 2591-76-6 ]
  • [ 570416-09-0 ]
YieldReaction ConditionsOperation in experiment
59.6% N,N-Diisobutylformamide (5.44 g, 34.5 mmol) was dissolved in chloroform (25.0 mL) and cooled in an ice-sodium chloride bath, and phosphorus oxychloride (3.22 mL, 34.5 mmol) was added dropwise thereto at -2C or less. After the mixture was stirred at -2C or less for 30 minutes, 2,6-dichloroimidazo[1,2-b]pyridazin-3-ylsulfonamide (6.15 g, 23.0 mmol) was added thereto. After the mixture was stirred at -10C for 10 minutes, triethylamine (19.3 mL, 138 mmol) was added dropwise over 20 minutes to the solution at 5C or less. The mixture was stirred for 1 hour at 0C or less and for 1 hour at room temperature, then poured into an aqueous saturated sodium bicarbonate and extracted 5 times with chloroform. The extracts were combined, dehydrated over anhydrous magnesium sulfate and concentrated under reduced pressure. The residues were purified by silica gel column chromatography (ethyl acetate : hexane = 1 : 1) to give the title compound as pale yellow crystals. The yield was 5.58 g (59.6%). mp 151.0-154.0C1H NMR(CDCl3, δ): 0.76(6H, d, J=6.7 Hz), 0.97 (6H, d, J=6.7 Hz), 1.90-2.10(2H, m), 3.23(2H, d, J=7.6 Hz), 3.28(2H, d, J=7.7 Hz), 7.26(1H, d, J=9.5 Hz), 7.90(1H, d, J=9.5 Hz), 8.51(1H, s). IR(Nujol, cm-1): 1615, 1456, 1324, 1311, 1146, 910, 858, 654.
  • 14
  • [ 75-77-4 ]
  • disodium pentacarbonylchromium [ No CAS ]
  • [ 2591-76-6 ]
  • [ 117041-08-4 ]
  • 15
  • [ 2591-76-6 ]
  • 4-amino-3-hydro-7-(3,5-di-O-toluoyl-2-deoxy-beta-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2-one [ No CAS ]
  • [ 50746-36-6 ]
  • 4-(N,N-diisobutyl-formamidine)-3-hydro-7-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; 4-Amino-3-hydro-7-(3,5-di-O-toluoyl-2-deoxy-β-D-ribofuranosyl)-pyrrolo[2,3-d]pyrimidin-2-one (1.014 g, 2.02 mmol) is dissolved in CH2Cl2 (10 mL), Dimethoxymethyldiisobutylamine (2.5 mL of a 70% w/w solution in diisobutylformamide) is added dropwise. The solution is allowed to stir at room temperature overnight. The mixture is concentrated to small bulk (yellow oil) and resolved by chromatography using gradients of methylene chloride and methanol to afford a mixture of the two isomers. The mixture is then repurified to resolve the two isomers.
  • 16
  • [ 2955-86-4 ]
  • [ 2591-76-6 ]
  • 18
  • [ 19244-89-4 ]
  • [ 2591-76-6 ]
YieldReaction ConditionsOperation in experiment
51% With tris(2 2'-bipyridyl)ruthenium(II) chloride hexahydrate; oxygen; caesium carbonate; In acetonitrile; at 20℃; for 16h;Irradiation; Inert atmosphere; General procedure: A flame-dried round bottom flask (10 mL) was equipped with magnetic stirring barand charged with enamine compound (0.4 mmol, 1.0 equiv), tris(2,2-bipyridyl)ruthenium(II) chloride hexahydrate (0.01 mmol, 0.025 equiv) and MeCN (2.0 mL). Themixture was then added Cs2CO3 (0.4 mmol, 1.0 equiv), and irradiated by a householdbulb (45 W) under a balloon oxygen atmosphere at room temperature until the startingmaterial disappeared from the TLC. The reaction mixture was filtrated through celiteand washed with ether. The solvent was removed under reduced pressure, the residuewas purified by silica gel column chromatography to afford desired pure product 8-10 in 40-99% yield.
  • 19
  • [ 110-96-3 ]
  • [ 60100-09-6 ]
  • [ 2591-76-6 ]
  • 20
  • [ 110-96-3 ]
  • [ 96-26-4 ]
  • [ 2591-76-6 ]
YieldReaction ConditionsOperation in experiment
83% With Cu/Al2O3; dihydrogen peroxide; In water; at 25℃; for 24h;Green chemistry; General procedure: The catalyst A 25 mg prepared in Example 1 was weighed, added to a 38 mL reaction tube with magnetic stirring, and then 465 mg (5 mmol) of aniline, 90 mg (1 mmol) of 1,3-dihydroxyacetone, 0.5 mL (6 mmol) 35% hydrogen peroxide and 5 mL chloroform. Thereafter, the temperature was raised to 50 C using an electric heating furnace and maintained for 12 hours. Then, the reaction tube was cooled to room temperature by water cooling, centrifuged at 8000 rpm for 5 minutes using a centrifuge (Shanghai Anting Scientific Instrument Factory), and separated to recover Catalyst A from the reaction mixture. Using N-formylated aniline standard product as a comparison, qualitative and quantitative analysis was performed using HP 6890/5973 GC-MS gas chromatography mass spectrometer and Agilent 7890A (30m×0.25mm×0.33μm capillary column, hydrogen flame ionization detector). A well-known method in the art, such as an industrial rectification process, obtains the target product N-formylated aniline, and the yield results are shown in Table 1 below.
  • 21
  • [ 123-91-1 ]
  • [ 110-96-3 ]
  • [ 2591-76-6 ]
 

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