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Chemical Structure| 2919-23-5 Chemical Structure| 2919-23-5

Structure of Cyclobutanol
CAS No.: 2919-23-5

Chemical Structure| 2919-23-5

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Product Details of [ 2919-23-5 ]

CAS No. :2919-23-5
Formula : C4H8O
M.W : 72.11
SMILES Code : OC1CCC1
MDL No. :MFCD00001318
InChI Key :KTHXBEHDVMTNOH-UHFFFAOYSA-N
Pubchem ID :76218

Safety of [ 2919-23-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210
Class:3
UN#:1987
Packing Group:

Computational Chemistry of [ 2919-23-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 5
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 0
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 20.39
TPSA ?

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

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.37
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

0.45
Log Po/w (WLOGP)?

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

0.53
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.

0.35
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

1.09
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.76

Water Solubility

Log S (ESOL):?

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

-0.57
Solubility 19.4 mg/ml ; 0.269 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.

-0.44
Solubility 26.0 mg/ml ; 0.361 mol/l
Class?

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

Very 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

-0.04
Solubility 65.2 mg/ml ; 0.904 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

No
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.

-6.42 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

3.0
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

0.0 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)

1.05

Application In Synthesis of [ 2919-23-5 ]

* 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 [ 2919-23-5 ]

[ 2919-23-5 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 2919-23-5 ]
  • [ 123843-66-3 ]
  • 4-Cyano-3-fluoro-5-cyclobutyloxyanisole [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% (a) 4-Cyano-3-fluoro-5-cyclobutyloxyanisole The subtitle compound was prepared from 4-cyano-3,5-difluoroanisole and cyclobutanol following the procedure described in Example 14(a). The crude product was purified on silica gel eluding with dichloromethane:hexane (60:40 v/v) to give the subtitle compound as a white solid (92%). Rf 0.26 (dichloromethane:hexane 1:2, v/v). MS m/z 239 (MNH4)+.
  • 2
  • [ 2919-23-5 ]
  • [ 405939-39-1 ]
  • C12H17BrN2O2S [ No CAS ]
  • 3
  • [ 2919-23-5 ]
  • [ 112108-73-3 ]
  • [ 1445894-86-9 ]
  • 4
  • [ 2919-23-5 ]
  • [ 454-16-0 ]
  • 1-cyclobutoxy-2-methoxy-4-nitrobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In acetonitrile; mineral oil; at 35℃;Inert atmosphere; Example 42 Preparation of l-cyclobutoxy-2-methoxy-4-nitrobenzene [0287] In a 50 mL round bottom flask, cyclobutanol (0.42 g, 5.84 mmoles), sodium hydride (60percent) (0.47 g, 11.69 mmoles), l-fluoro-2-methoxy-4-nitrobenzene (1.00 g, 5.84 mmoles) was combined in acetonitrile (9 mL) and stirred under nitrogen overnight at 35°C. The mixture was quenched with water (30 mL) and extracted with ethyl acetate (30 mL x 3), dried over anhydrous sodium carbonate, filtered and the filtrate was concentrated. The residue was purified on a 40 g silica column and eluted off using a gradient of 0-40percent ethyl acetate / hexane. The desired fractions were concentrated to dryness under reduced pressure to provide title compound.
  • 5
  • [ 2106-50-5 ]
  • [ 2919-23-5 ]
  • 2-chloro-4-cyclobutoxy-1-nitrobenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of Nal-I (3.42 g, 85 mmol) in DMF (50 mL) was added dropwise cyclohutanol (6.16 g, 85 mrnoi), and the solution was stirred at 20 C for about 5 minutes. Then <strong>[2106-50-5]2-chloro-4-fluoro-1-nitrobenzene</strong> (10.OOg, 57.0mmoi) was added to the reaction, and the reaction was stirred for 18 h at room temperature.Saturated NH1C1 aqueous solution (100 inL) and EtOAc (100 mL) were added to the reaction.The organic layer was separated and washed with saturated NH4CI aqueous solution (100mLx4), dried over sodium sulfate and concentrated to give the title compound.
  • 6
  • [ 104711-65-1 ]
  • [ 2919-23-5 ]
  • C11H12N2O [ No CAS ]
  • 7
  • [ 7651-82-3 ]
  • [ 2919-23-5 ]
  • 6-cyclobutoxyisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 21h;Inert atmosphere; [CAS Reg. No. 1822782-90-0] DIAD (1.22 mL, 6.20 mmol) was added to a mixture of <strong>[7651-82-3]isoquinolin-6-ol</strong> (600 mg, 4.13 mmol), cyclobutanol (0.324 mL, 4.13 mmol) and PPh3 (1.63 g, 6.20 mmol) in anhyd THF (5 mL) at r.t. for 16 h. Additional PPh3 (1.63 g, 6.20 mmol) and DIAD (1.22 mL, 6.20 mmol) were added and the suspension was stirred at r.t. for a further 5 h. The mixture was loaded onto an SCX column; the column was first eluted with MeOH to remove by-products, then with 7 N ammonia in MeOH. Fractions containing the desired product were evaporated onto silica gel. The crude product was purified by flash silica gel chromatography (eluent: gradient 0 to 10percent MeOH in CH2Cl2). Fractions containing the desired product were combined and evaporated to dryness to afford the title compound 29 (800 mg, 97percent) as a yellow oil. MS (ES+): m/z = 200 [M + H]+.
  • 8
  • [ 221044-05-9 ]
  • [ 201230-82-2 ]
  • [ 2919-23-5 ]
  • C17H15N3O2 [ No CAS ]
 

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