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Chemical Structure| 36255-44-4 Chemical Structure| 36255-44-4

Structure of 3-Bromo-1,1-dimethoxypropane
CAS No.: 36255-44-4

Chemical Structure| 36255-44-4

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Product Details of [ 36255-44-4 ]

CAS No. :36255-44-4
Formula : C5H11BrO2
M.W : 183.04
SMILES Code : COC(OC)CCBr
MDL No. :MFCD00013245
InChI Key :ODZZAIFAQLODKN-UHFFFAOYSA-N
Pubchem ID :118932

Safety of [ 36255-44-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 36255-44-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 8
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 36.19
TPSA ?

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

18.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.23
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

1.21
Log Po/w (WLOGP)?

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

1.39
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.

1.19
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

1.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.44

Water Solubility

Log S (ESOL):?

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

-1.47
Solubility 6.16 mg/ml ; 0.0336 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.

-1.19
Solubility 11.7 mg/ml ; 0.0639 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

-1.85
Solubility 2.61 mg/ml ; 0.0143 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.

-6.56 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

2.0 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)

2.47

Application In Synthesis of [ 36255-44-4 ]

* 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 [ 36255-44-4 ]

[ 36255-44-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 36255-44-4 ]
  • [ 93247-78-0 ]
  • [ 1262419-90-8 ]
YieldReaction ConditionsOperation in experiment
92% Step A: To a stirred solution of methyl lH-indole-7-carboxylate (3.3 g,18.8 mmol) in DMSO (18 mL) was added potassium ter/-butoxide (2.1 g, 18.8 mmol) in portions. After stirring at room temperature for 1 h, a solution of 3-bromo-l ,l- dimethoxypropane (1O g, 54.6 mmol) and potassium iodide (188 mg, 1.1 mmol) in DMSO (15 mL) was added and the mixture was stirred for 15 h. The reaction was quenched with saturated aqueous ammonium chloride and adjusted to pEta 6. The aqueous phase was extracted with ethyl acetate (3x) and the combined extracts were washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified by column chromatography (silica gel, 90: 10 hexanes/ethyl acetate) to give methyl l-(3,3- dimethoxypropyl)-lH-indole-7-carboxylate (4.8 g, 92percent) as a light yellow oil: 1H NMR (500 MHz, CDCl3) delta 7.79 (d, J = 7.5 Hz, 1 H), 7.68 (d, J = 7.5 Hz, 1 H), 7.12 (d, J = 3.0 Hz, I H), 7.1 1 (t, J = 7.5 Hz, I H), 6.56 (d, J = 3.5 Hz, I H), 4.49 (t, J= 7.0 Hz, 2H), 4.09 (t, J= 6.0 Hz, IH), 3.97 (s, 3H), 3.25 (s, 6H), 1.97 (q, J= 6.0 Hz, 2H).
  • 2
  • [ 55687-30-4 ]
  • [ 36255-44-4 ]
  • 1-(3,3-dimethoxypropyl)-7-methoxyquinoxalin-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% 7-Methoxyquinoxalin-2(1 H)-one (synthesized with reference to WO2009/1126; 4.13 g, 23.4 mmol) was dissolved in N,N-dimethylformamide (103 ml). The solution was cooled in an ice bath, lithium hydride (purity 90%, 248 mg, 28.1 mmol) was then added thereto and the mixture was stirred at room temperature for 40 minutes. The reaction solution was cooled in an ice bath again, 3-bromo-1,1-dimethoxypropane (3.78 ml, 28.1 mmol) and sodium iodide (4.21 g, 28.1 mmol) were added and then the mixture was stirred at room temperature for 2 days. The reaction solution was diluted with ethyl acetate, washed sequentially with saturated sodium chloride solution (X2), water and saturated sodium chloride solution, dried over magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 4.68 g (72%) of the title compound in the form of a yellow syrup. 1H-NMR(400MHz,CDCl3)δ:2.02-2.09(2H,m),3.38(6H,s),3.92(3H,s),4.27-4.30(2H,m),4.50(1H,t,J=5.2Hz),6.90-6.93(2H,m),7.77(1 H,t,8.6Hz),8.12(1 H,s). MS(ESI)m/z:279(M+H)+.
  • 3
  • [ 36255-44-4 ]
  • [ 15944-34-0 ]
  • 7-chloro-1-(3,3-dimethoxypropyl)-1,2-dihydro-1,8-naphthyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 4h; A mixture of 7-chloro-1 ,2-dihydro-1 ,8-naphthyridin-2-one (1 g, 5.53 mmol), 3-bromo-1 , 1- dimethoxypropane (1.1 g, 6.09 mmol) and K2CO3 (1.1 g, 8.31 mmol) in DMF (20 mL) was heated at 70C for 4 h. The mixture was then allowed to cool to room temperature, poured into H2O (30 mL) and extracted with EtOAc (30 mL x 3). The combined organic extracts were washed with H2O (50 mL x 2), brine (50 mL), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography using 30% EtOAc/petroleum ether to give a yellow solid of 7-chloro-1-(3,3- dimethoxypropyl)-1 ,2-dihydro-1 ,8-naphthyridin-2-one 6a (1 g, 64%). TLC : Rf = 0.54 (silica gel, EtOAc/petroleum ether = 1 : 1 , v/v).
 

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