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Chemical Structure| 126-86-3 Chemical Structure| 126-86-3

Structure of 126-86-3

Chemical Structure| 126-86-3

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Product Details of [ 126-86-3 ]

CAS No. :126-86-3
Formula : C14H26O2
M.W : 226.36
SMILES Code : CC(C)CC(C)(O)C#CC(C)(O)CC(C)C
MDL No. :MFCD00008942
InChI Key :LXOFYPKXCSULTL-UHFFFAOYSA-N
Pubchem ID :31362

Safety of [ 126-86-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H319-H373
Precautionary Statements:P501-P260-P264-P280-P314-P337+P313

Computational Chemistry of [ 126-86-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 0
Fraction Csp3 0.86
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 69.97
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.

3.18
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

2.74
Log Po/w (WLOGP)?

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

2.66
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.

2.88
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

2.9
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.87

Water Solubility

Log S (ESOL):?

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

-2.71
Solubility 0.446 mg/ml ; 0.00197 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.

-3.24
Solubility 0.129 mg/ml ; 0.00057 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

-2.15
Solubility 1.61 mg/ml ; 0.00711 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

Yes
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.

-5.74 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

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

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)

4.76

Application In Synthesis of [ 126-86-3 ]

* 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 [ 126-86-3 ]

[ 126-86-3 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 126-86-3 ]
  • [ 100912-23-0 ]
  • 2
  • [ 107-54-0 ]
  • [ 126-86-3 ]
  • 3
  • [ 108-10-1 ]
  • [ 74-86-2 ]
  • [ 107-54-0 ]
  • [ 126-86-3 ]
  • 4
  • [ 108-10-1 ]
  • [ 107-54-0 ]
  • [ 126-86-3 ]
  • 5
  • [ 126-86-3 ]
  • [ 92318-61-1 ]
  • 6
  • [ 126-86-3 ]
  • [ 17913-76-7 ]
  • 7
  • [ 126-86-3 ]
  • [ 149079-55-0 ]
  • 10
  • [ 108-10-1 ]
  • calcium carbide [ No CAS ]
  • [ 126-86-3 ]
  • 11
  • sodium salt of 2.4-dimethyl-hexyn-(5)-ol-(4) [ No CAS ]
  • [ 126-86-3 ]
  • 12
  • [ 60-29-7 ]
  • [ 107-54-0 ]
  • sodium [ No CAS ]
  • [ 126-86-3 ]
  • [ 3329-48-4 ]
  • 13
  • [ 126-86-3 ]
  • Ni(1,5,9-cyclododecatriene) [ No CAS ]
  • [ 175728-88-8 ]
  • 14
  • [ 1295-35-8 ]
  • [ 126-86-3 ]
  • [ 175728-89-9 ]
  • 15
  • [ 12130-66-4 ]
  • [ 126-86-3 ]
  • [ 175728-91-3 ]
  • 16
  • [ 126-86-3 ]
  • [ 1423124-94-0 ]
YieldReaction ConditionsOperation in experiment
99% With hydrazine hydrate; In ethanol; at 20 - 80℃; for 24.0h; 2,4,7,9-tetramethyl-5-yne-4,7-decanediol (1.13 g, 5 mmol), hydrazine mass percentage concentrationThe reaction was heated to 80 C for 24 hours. The reaction was stopped, the reaction was cooled to room temperature, and the ethanol was distilled off under reduced pressure. The reaction mixture was cooled to 80 C, , With 10 ml of dichloromethane dissolved, 5 ml of water 2 washing, drying at room temperature with anhydrous sodium sulfate 2h, filter desiccant, the solvent evaporated to get viscous liquid (Z) -2,4,7,9- 4,7-decanediol; dissolving the viscous liquid with 2 mL of methylene chloride, over a silica gel column, eluting with methylene chloride / ethyl acetate (4/1 by volume)To give (Z) -2,4,7,9-tetramethyl-5-ene-4,7-decanediol as a pure product1.06 g, yield 99%.
227 mg With [1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene]copper(I) tert-butoxide; tert-butyl alcohol; In toluene; at 40℃; for 8.0h;Inert atmosphere; Glovebox; General procedure: 4.4 General procedure for the reduction of internal alkynes In a nitrogen-filled glovebox, a 1-dram vial was charged with a stir bar followed by the alkyne (1.00equiv, 1.00mmol), PMHS 8 (2.00equiv, 120mg, 2.00mmol), and tert-butanol (2.50equiv, 185mg, 2.50mmol). This mixture was diluted in toluene (2mL) before adding IPrCuOt-Bu 14 (0.020equiv, 11mg, 0.020mmol). The reaction mixture was stirred at 40C until complete conversion of the starting material was achieved (8h). The mixture was then diluted with hexanes (20mL), and filtered through a silica gel plug using a 1:1 ethyl acetate/hexane solution (100mL). The filtrate was concentrated under vacuum, and the crude reaction products were purified using a 10g silica gel column (see selected examples below for mobile phase used). 4.4.1.1 (Z)-2,4,7,9-Tetramethyldec-5-ene-4,7-diol (47) Compound was isolated as a white solid (227 mg, 99% yield) after a THF/NaOH workup followed by silica gel chromatography (0-40% ethyl acetate/hexanes over eight column volumes). 1H NMR (300 MHz, CDCl3) delta 5.30 (s, 2H), 4.32 (s, 2H), 1.83 (qt, J=12.9, 6.4 Hz, 2H), 1.51 (d, J=6.0 Hz, 4H), 1.34 (s, 6H), 0.96 (d, 4.7 Hz, 6H), 0.94 (d, J=6.6, 6H). 13C NMR (126 MHz, CDCl3) delta 135.4, 74.1, 52.8, 31.0, 24.9, 24.8, 24.7. HRMS calculated for [M+Na]+ 251.1987, found 251.1991. FTIR (neat, cm-1): 3219 (br), 3004 (w), 2954 (s), 1158 (s).
  • 17
  • [ 108-10-1 ]
  • [ 74-86-2 ]
  • [ 126-86-3 ]
YieldReaction ConditionsOperation in experiment
84.1% With potassium hydroxide; In cyclohexane; at 40 - 45℃; under 750.075 Torr; for 5.5h;Autoclave; Inert atmosphere; The concentrated alkali liquor in Example 1 was dehydrated under reduced pressure to obtain 14 g of a paste.The paste was mixed with 10 g of a novel complex catalyst, 100 g of methyl isobutyl ketone, 40 g of cyclohexane, and 31 g of diethylene glycol divinyl ether distilled in Example 1, and put into a 500-mL autoclave.Replace air with nitrogen, control temperature 40~45C, pass acetylene into the reaction system for acetylene reaction, keep the system pressure no higher than 0.1MPa,When 11.7 g of acetylene was passed, the pressure of the system was maintained for 10 min and no longer decreased, and the reaction was stopped. At this point, the reaction had been completed for 5.5 h.After cooling down to room temperature, the reaction solution in the autoclave was transferred to a 500 mL beaker and 10 g of deionized water was added to the beaker. The system was divided into two layers.26 g of concentrated lye containing lower lye was separated and transferred to a 250 mL beaker. The organic layer was neutralized with 20% phosphoric acid solution to pH 6-7. The brine was separated to obtain 190 g of organic phase.The organic phase was transferred to a 250 mL three-necked flask, and 17 g of the semi-finished acetylene glycol product of Example 1 was introduced. 37 g of cyclohexane was distilled out at normal pressure and distilled under reduced pressure.At a vacuum of -0.098 MPa, 1.5 g of a low-boiling substance was obtained at 60C, 31 g of a fore fraction was obtained at 60 to 90C, and 28 g of diethylene glycol divinyl ether was obtained at 90 to 120C.120 g of the acetylene glycol semi-finished product was obtained at 120 to 150 C., and 85.5 g of the acetylene glycol product was collected at 150 to 155 C. The heating was stopped, and the temperature was lowered to room temperature. 2 g of the high-boiling residue was left in the beaker.The yield of finished acetylenic diol (relative to acetylene) was 84.1%. Weigh 20g of potassium hydroxide and 200 diethylene glycol divinyl ether in a 500mL three-necked flask, heat to 60C to stir the reaction, and stop the reaction when potassium hydroxide is completely dissolved.The above-prepared complex catalyst is weighed out by weighing 50 g with 100 g of methyl isobutyl ketone, 50 g of cyclohexane, and put into a 500-mL high-pressure experimental kettle to make a bottom, nitrogen is substituted for air, and the temperature is controlled at 40-45 C.Acetylene was introduced into the reaction system for acetylene reaction to maintain the pressure of the system not higher than 0.1 MPa. When acetylene was introduced to 10.4 g, the pressure of the system was maintained for 10 min and no longer decreased, and the reaction was stopped. At this time, the reaction had been performed for 6 h.After cooling down to room temperature, the reaction solution in the autoclave was transferred to a 500 mL beaker. 10 g of deionized water was added to the beaker, and the system was divided into two layers. The concentrated lye containing 23 g of the lower oxime was separated and transferred to a 250 mL beaker. The organic layer was neutralized to pH 6~7 with a 20% phosphoric acid solution, and the brine layer was separated to obtain 185 g of an organic phase.The organic phase was transferred to a 250 mL three-necked flask, and 46 g of cyclohexane was distilled off at normal pressure, followed by distillation under reduced pressure. At a pressure of -0.098 MPa, 1 g of a low-boiling substance was obtained at 60C, 18 g of a fore fraction was obtained at 60 to 90C, and 31 g of diethylene glycol divinyl ether was obtained at 90 to 120C.A acetylene glycol semi-finished product of 17 g was obtained at 120 to 150 C., 69 g of acetylene glycol product was collected at 150 to 155 C., heating was stopped, and the temperature was lowered to normal temperature, and 3 g of the high-boiling residue was left in the beaker.The yield of finished acetylenic diol (relative to acetylene) was 76.3%.
 

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