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Chemical Structure| 13362-52-2 Chemical Structure| 13362-52-2

Structure of Tridecane-1,13-diol
CAS No.: 13362-52-2

Chemical Structure| 13362-52-2

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Product Details of [ 13362-52-2 ]

CAS No. :13362-52-2
Formula : C13H28O2
M.W : 216.36
SMILES Code : OCCCCCCCCCCCCCO
MDL No. :MFCD00482067
InChI Key :HCEPYODGJFPWOI-UHFFFAOYSA-N
Pubchem ID :11063855

Safety of [ 13362-52-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 13362-52-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 12
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 66.93
TPSA ?

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

40.46 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.31
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

4.08
Log Po/w (WLOGP)?

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

3.26
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.

2.76
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

3.78
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.44

Water Solubility

Log S (ESOL):?

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

-2.96
Solubility 0.237 mg/ml ; 0.0011 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-4.63
Solubility 0.00502 mg/ml ; 0.0000232 mol/l
Class?

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

Moderately 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

-4.0
Solubility 0.0217 mg/ml ; 0.0001 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

Yes
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

Yes
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.

-4.72 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

1.0
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

0.0
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<3.0
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)

2.0

Application In Synthesis of [ 13362-52-2 ]

* 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 [ 13362-52-2 ]

[ 13362-52-2 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 13362-52-2 ]
  • [ 116754-58-6 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen bromide; In water; toluene; for 48h;Reflux; Place a 1,13-tridecanol (21.6 g, 100 mmol) in a 500 mL round bottom flask,Toluene (analytical grade, 250 mL) and a 48 wt% aqueous solution of hydrobromic acid (13.5 mL, 120 mmol), the reaction mixture was stirred at reflux for 48 h.TLC detection until the material disappears. After the reaction solution was cooled to room temperature, it was diluted with n-hexane.The obtained organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and dried over anhydrous sodium sulfate. After the solvent was distilled off,13-bromo-1-tridecanol (27.5 g, 99%) was obtained.The obtained product 13-bromo-1-tridecanol has high purity and can be directly used in the next reaction.
99% With hydrogen bromide; In water; toluene; for 48h;Reflux; In a 500 mL round-bottom flask, place 1,13-tridecanediol (21.6 g, 100 mmol), toluene (analytical grade, 250 mL) and 48 wt% aqueous hydrobromic acid solution (13.5 mL, 120 mmol),The reaction mixture was stirred at reflux for 48h. TLC detection until the raw material disappears. After the reaction solution was cooled to room temperature, it was diluted with n-hexane.After washing the obtained organic phase with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and after evaporating the solvent,13-Bromo-1-tridecyl alcohol (27.5 g, 99%) was obtained.The resulting product 13-bromo-1-tridecyl alcohol has a higher purity and can be directly used in the next reaction
98% With hydrogen bromide; In water; toluene; for 22h;Dean-Stark; Reflux; To a suspension of 40 (5.0 g, 23.1 mmol) in toluene (130 mL) was added HBr (48% aq., 2.9 mL, 25.4 mmol). The mixture was refluxed for 17 hr, while trapping the water by using a Dean-Stark trap. An aliquot was taken and evaporated to dryness. NMR showed it still contained 40. Additional HBr (48% aq., 8.1 mL, 71 mmol) and toluene (60 mL) were added and continued to reflux for additional 5 hr, trapping the water by using a Dean-Stark trap. Stop the reaction. The reaction mixture was evaporated to dryness to leave the crude product 41 (6.3 g, 98%) as off-white solid. 'H NMR (500 MHz, Chloroform-ri) d 3.64 (t, J= 6.6 Hz, 2H), 3.41 (t, .7= 6.9 Hz, 2H), 1.85 (dt, J= 14.5, 7.0 Hz, 2H), 1.66 - 1.49 (m, 2H), 1.49 - 1.17 (m, 19H).
67% With hydrogen bromide; In cyclohexane; water; for 3h;Reflux; Inert atmosphere; Aqueous HBr (48%, 16 mL) was added under vigorous stirring to diol 11 (2.644 g, 12.22 mmol, 1.00 equiv) suspended in cyclohexane (32 mL). The mixture was stirred and heated to reflux for 3 h, and the aqueous phase was separated after cooling to r.t. and extracted with EtOAc (3 30 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The remainder was purified by column chromatography (cyclohexane/EtOAc, 3:1) to afford the title compound. Yield: 2.284 g (8.179 mmol, 67%); colourless solid; mp 54-55 C (lit.6b mp 56-57 C); Rf = 0.51 (cyclohexane/EtOAc, 3:1). IR (ATR): 3428, 2917, 2851, 1468, 1355, 1327, 1253, 1205, 1058, 1049, 1025, 1010, 995, 969, 722, 645, 604, 570 cm-1. 1H NMR (CDCl3, 500 MHz): δ = 3.64 (dt, J = 5.5, 6.5 Hz, 2 H, 1-H), 3.41 (t, J = 7.0 Hz, 2 H, 13-H), 1.85 (quin, J = 7.0 Hz, 2 H, 12-H), 1.57 (quin, J = 6.5 Hz, 2 H, 2-H), 1.46-1.24 (m, 18 H, 3-H to 11-H), 1.19 (t, J = 5.5 Hz, 1H, OH). 13C NMR (CDCl3, 125 MHz): δ = 63.3, 34.3, 32.98, 32.96, 29.74, 29.70, 29.67, 29.57, 28.92, 28.33, 25.9.
52% With hydrogen bromide; In water; toluene; at 0℃; for 18h;Inert atmosphere; Reflux; To a solution of 43 (7.2 g, 33 mmol) in toluene (105 mL) was added48% aq HBr (4.5 mL, 40 mmol) at 0 C. After stirring for 18 h underreflux conditions, the completion of the reaction was confirmed by TLC(1:1 n-hexane/EtOAc). The reaction mixture was diluted with EtOAcand washed with washed with 1m aq NaOH and brine. The organiclayer was subsequently dried over Na2SO4, filtered, and concentrated.The resulting residue was purified by silica gel column chromatography(4:1 n-hexane/EtOAc) to give 44 (4.9 g, 52%) as white powder. 1H NMR(500 MHz, CDCl3) δ 3.64 (near d, 2H, CH2OH), 3.41 (t, 2H,Jvic=7.0 Hz, CH2Br), 1.89-1.82 (m, 2H, CH2CH2Br), 1.60-1.54 (m,2H, CH2CH2OH), 1.42 (near t, 2H, CH2CH2CH2Br), 1.36-1.27 (m, 17H,-CH2-, OH); 13C NMR (125 MHz, CDCl3) δ 63.1, 34.1, 32.9, 32.8, 29.6,29.6, 29.6, 29.5, 29.4, 28.8, 28.3, 25.8. HRMS (ESI) m/z: found [M+Na]+ 301.1136, C13H27OBr calcd for [M+Na]+ 301.1137.

 

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