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Chemical Structure| 626-18-6 Chemical Structure| 626-18-6

Structure of 626-18-6

Chemical Structure| 626-18-6

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Product Details of [ 626-18-6 ]

CAS No. :626-18-6
Formula : C8H10O2
M.W : 138.16
SMILES Code : OCC1=CC=CC(CO)=C1
MDL No. :MFCD00004649
InChI Key :YWMLORGQOFONNT-UHFFFAOYSA-N
Pubchem ID :69374

Safety of [ 626-18-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H319
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 626-18-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.25
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 38.7
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.

1.7
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

0.17
Log Po/w (WLOGP)?

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

0.37
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.

0.94
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

1.52
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.94

Water Solubility

Log S (ESOL):?

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

-1.12
Solubility 10.6 mg/ml ; 0.0766 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.

-0.58
Solubility 36.6 mg/ml ; 0.265 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

-2.03
Solubility 1.3 mg/ml ; 0.0094 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

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

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

Yes
Log Kp (skin permeation)?

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

-7.02 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

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)

1.0

Application In Synthesis of [ 626-18-6 ]

* 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 [ 626-18-6 ]

[ 626-18-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 626-18-6 ]
  • [ 175464-51-4 ]
YieldReaction ConditionsOperation in experiment
50% With thionyl chloride; In hexane; chloroform; ethyl acetate; EXAMPLE 2 m-Hydroxymethylbenzyl chloride 1,3-benzenedimethanol (27.772 g, 0.201 mole) was charged to a 500 mL round-bottom flask equipped with a septum inlet and a nitrogen adapter connected to a gas scrubber. The mixture was placed in an ice bath and cooled to 0 C. Thionyl chloride (14.66 mL, 0.201 mole), dissolved in chloroform (200 mL) was added slowly via syringe and the mixture stirred at 0 C. for 15 minutes followed by continued stirring at room temperature for 18 hours. TLC analysis of a sample removed after one hour of stirring at room temperature showed little reaction product formed. After 18 hours, TLC analysis indicated that the product was present. The mixture was concentrated as in Example 1 and the residue purified on a silica gel column (700 g) using 1:3 ethyl acetate:hexane followed by 1:2 ethyl acetate:hexane. The title compound, m-hydroxymethylbenzyl chloride, was obtained as a colorless oil (19.39 g) in 61.6% yield. The results of Examples 1 and 2 demonstrate that greater than 50% yields of hydroxy halides were obtained by the method of the invention.
With hydrogenchloride; In water; toluene; at 10 - 30℃; for 8h; Production Example 1113- {2- [5- (4-acetylpiperazin-l-yl)pyridin-2-yl] ethyl }benzyl hydrazinecarboxylate trihydrochloride step 1. [0360] [0361] To a solution of m-xylyleneglycol (2.763 g, 20.00 mmol) in toluene (100 ml) was added concentrated hydrochloric acid (10 ml) , and the mixture was stirred at room temperature for 8 hrs . Water (50 ml) was added and the mixture was stirred.Saturated aqueous sodium hydrogen carbonate (120 ml) was added, and the mixture was stood still and partitioned. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.The residue was dissolved in toluene (10 ml) , and triphenylphosphine (5.249 g, 20.00 mmol) was added. The mixture was heated under reflux for 14 hrs, and cooled to room temperature. The precipitated solid was collected by filtration, washed with a mixture of tert-butyl methyl ether, methanol (1 ml) and ethyl acetate (50 ml) and dried under reduced pressure to give [3- ' (hydroxymethyl) benzyl] (triphenyl) chloride (3.898 g, yield46.5%) as a white solid.
 

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Technical Information

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