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Chemical Structure| 3279-95-6 Chemical Structure| 3279-95-6

Structure of 2-(Aminooxy)ethanol
CAS No.: 3279-95-6

Chemical Structure| 3279-95-6

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Product Details of [ 3279-95-6 ]

CAS No. :3279-95-6
Formula : C2H7NO2
M.W : 77.08
SMILES Code : NOCCO
MDL No. :MFCD00517034
InChI Key :WWWTWPXKLJTKPM-UHFFFAOYSA-N
Pubchem ID :3014186

Safety of [ 3279-95-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225
Precautionary Statements:P210-P403+P235
Class:3
UN#:1993
Packing Group:

Computational Chemistry of [ 3279-95-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 5
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 16.68
TPSA ?

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

55.48 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.57
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

-1.35
Log Po/w (WLOGP)?

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

-1.13
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.

-1.22
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

-1.05
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-0.84

Water Solubility

Log S (ESOL):?

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

0.66
Solubility 356.0 mg/ml ; 4.62 mol/l
Class?

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

Highly soluble
Log S (Ali)?

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

0.68
Solubility 373.0 mg/ml ; 4.84 mol/l
Class?

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

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

0.63
Solubility 329.0 mg/ml ; 4.27 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.

-7.73 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

2.0
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)

2.04

Application In Synthesis of [ 3279-95-6 ]

* 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 [ 3279-95-6 ]

[ 3279-95-6 ] Synthesis Path-Downstream   1~35

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YieldReaction ConditionsOperation in experiment
97% In ethanol; for 18h;Reflux; A mixture of 2-(aminooxy)ethanol (3.16 g, 41.0 mmol) and paraformaldehyde (1.23 g, 41.0 mmol) in EtOH (50 ml_) was heated under reflux for 18 h. The solvent was removed under reduced pressure to afford the subtitle compound formaldehyde 0-(2-hydroxyethyl) oxime as a colourless oil (3.56 g, 97%); 1 H NMR delta: 3.57 (2H, q), 4.05-3.96 (2H, m), 4.67 (1 H, t), 6.57 (1 H, d), 7.05 (1 H, d).
  • 3
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YieldReaction ConditionsOperation in experiment
78% With hydrazine; In methanol; at 70℃; for 1.5h; 13b. 2-(Aminooxy)ethan-l-olH2N. / LambdaDHA solution of the product of Example 13a (15.57 g, 75.2 mmol) and hydrazine hydrate (5.4 mL, 0.11 mol) in methanol (150 mL) were heated to 70 C for 1.5 hours. After cooling to room temperature, CHCl3 (100 mL) was added to the reaction mixture. The resulting slurry was filtered and washed with CHCl3 (100 mL x 2). The filtrate was concentrated and the residue was distilled under vacuum (0.025 mmHg) at 75 to 80 C to give a colorless oil (4.54 g, 78% yield); 1H NMR (300 MHz, CDCl3) delta 3.78 (s, 4H); 13C NMR (75 MHz, CDCl3) delta 76.3, 60.7.
73% With methylhydrazine; In dichloromethane; at 20℃; 2 was obtained flask 5L in step 4 (2-hydroxy - ethoxy) - isoindole-1,3-dione (555 g, 2.679 mol) was added, dissolved under stirring in methylene chloride (2.0 L), while the reaction vessel was cooled in an ice bath, methyl hydrazine (142 mL, 2.68 mol) the inner temperature was added dropwise so as not to exceed 20 C. With the progress of the reaction, a white insoluble matter has emerged. After completion of the dropwise addition, the mixture was stirred under about 15 minutes the ice bath, the precipitated insoluble substance was filtered off through a glass filter, washed white insolubles on the filter with dichloromethane (2 x 400 mL), the filtrate and washings was combined evaporated under reduced pressure. The yellow oily residue (230g) was distilled under reduced pressure (51~54 C / 2 mmHg), the objective compound as unemployed transparent liquid 2-aminooxyethanol (162g, 73%).
28% With hydrazine hydrate; In methanol; at 70℃; for 1.5h; To a stirred solution of Compound 172 (29.0 g, 139.97 mmol) in MeOH (300 mL) was added hydrazine hydrate (9.63 mL, 195.96 mmol) at room temperature. The resultant solution was stirred at 70 C for 1.5 hours. The reaction mixture was cooled to room temperature and diluted with CHCI3(1 x 300 mL). The resultant slurry was filtered through Buchner funnel and washed with CHCI3(2 x 300 mL). The filtrate was concentrated, and the residue was distilled under vacuum (0.025 mmHg) at 75-80 C to give the desired alcohol, 2-(aminooxy)ethan-1-ol (Compound 173, 3.0 g,28 %), as a colorless oil.
With hydrazine hydrate; In methanol; for 2h;Reflux; Hydrazine monohydrate (3.96 mg, 0.124 mmol) was added to a solution of 2-(2- hydroxyethoxy)isoindoline-1 ,3-dione (produced with a similar procedure for intermediate B) (25.6 mg, 0.124 mmol) in 5 ml_ of MeOH. The solution was heated at reflux for 2 h and then cooled to rt. White precipitate was filtered off and 1 -(3-(quinolin-6-ylmethyl)- [1 ,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (41.2) (15 mg, 0.049 mmol) was added. The pH value of the solution was adjusted to 5-6 with 1 N HCI solution. The reaction solution was then stirred at rt for 2 h. Solvent was evaporated and the crude was purified by HPLC (acidic with 0.05% TFA) to give 8 mg (44.5%) of the title compound as a white TFA salt. 1H-NMR (400MHz, MeOH-Cf4) delta ppm 9.09 (s, 1 H), 8.93 (d, 1 H), 8.27 (s, 1 H), 8.16 (m, 3H), 7.98 (d, 1 H), 7.93 (m, 1 H), 4.92 (s, 2H), 4.38 (t, 2H), 3.86 (t, 2H), 2.34 (s, 3H). LC-MS (method B): [MH]+ =363.1 , tR = 2.31 min.

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  • [ 103-71-9 ]
  • [ 93312-14-2 ]
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  • (R)-2-((E)-(1R,9S,12S,14S,15R,19S,21S,22R,23S,25R)-15-Ethyl-1,14-dihydroxy-21,23-dimethoxy-17,19,25-trimethyl-2,3,10-trioxo-11,26-dioxa-4-aza-tricyclo[20.3.1.04,9]hexacos-16-en-12-yl)-propionaldehyde [ No CAS ]
  • (S)-2-((E)-(1R,9S,12S,14S,15R,19S,21S,22R,23S,25R)-15-Ethyl-1,14-dihydroxy-21,23-dimethoxy-17,19,25-trimethyl-2,3,10-trioxo-11,26-dioxa-4-aza-tricyclo[20.3.1.04,9]hexacos-16-en-12-yl)-propionaldehyde O-(2-hydroxy-ethyl)-oxime [ No CAS ]
  • (S)-2-((E)-(1R,9S,12S,14S,15R,19S,21S,22R,23S,25R)-15-Ethyl-1,14-dihydroxy-21,23-dimethoxy-17,19,25-trimethyl-2,3,10-trioxo-11,26-dioxa-4-aza-tricyclo[20.3.1.04,9]hexacos-16-en-12-yl)-propionaldehyde O-benzyl-oxime [ No CAS ]
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  • N-[5(S)-3-[3-fluoro-4-[(1α,5α,6α)-6-[(2-hydroxyethoxy) iminomethyl]-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
The title compound N-[5(S)-3-[3-fluoro-4-[(1alpha,5alpha,6alpha)-6-[(2-hydroxyethoxy) iminomethyl]-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (149 mg) was prepared from N-[5(S)-3-[3-fluoro-4-[(1alpha,5alpha,6alpha)-6-formyl-3-azabicyclo[3.1.0]hexan-3-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]acetamide (150 mg) and crude <strong>[3279-95-6]O-(2-hydroxyethyl)hydroxylamine</strong> (prepared from N-(2-hydroxyethoxy)phthalimide (414 mg)) in the same manner as described for EXAMPLE 66. MS (EI+) m/z: 420 (M+).
  • 28
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  • [ 60058-44-8 ]
  • (E,E)-17β-[3-[(2-hydroxyethoxy)imino]-1-propenyl]-5β-androstane-3β,14β-diol [ No CAS ]
  • 29
  • [ 3279-95-6 ]
  • [ 178692-06-3 ]
  • (E,E)-17β-[3-(2-hydroxyethoxy)imino-2-methyl-1-propenyl]-5β-androstane-3β,14β-diol [ No CAS ]
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  • [ 329015-72-7 ]
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  • [ 329015-71-6 ]
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  • (3S,6R,9S,12R,15S,18R,21S,24R)-6,18-Dibenzyl-3,9,15,21-tetraisobutyl-4,10,12,16,22,24-hexamethyl-23-thioxo-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosane-2,5,8,11,14,17,20-heptaone [ No CAS ]
  • (3S,6R,9S,12R,15S,18R,21S,24R)-6,18-Dibenzyl-3,9,15,21-tetraisobutyl-4,10,12,16,22,24-hexamethyl-1,7,13,19-tetraoxa-4,10,16,22-tetraaza-cyclotetracosan-2,5,8,11,14,17,20,23-octaone 11-[O-(2-hydroxy-ethyl)-oxime] [ No CAS ]
  • 33
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  • [ 205171-04-6 ]
  • C34H31N5O9 [ No CAS ]
  • 34
  • 24-O-tert-butyldimethylsilyl-22(R)-dihydro-28-oxoascomycin [ No CAS ]
  • [ 3279-95-6 ]
  • 14-(<i>tert</i>-butyl-dimethyl-silanyloxy)-17-ethyl-1,16-dihydroxy-12-[1-(2-hydroxy-ethoxyimino)-ethyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-28-oxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10-trione [ No CAS ]
  • 14-(<i>tert</i>-butyl-dimethyl-silanyloxy)-17-ethyl-1,16-dihydroxy-12-[1-(2-hydroxy-ethoxyimino)-ethyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-28-oxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10-trione [ No CAS ]
  • 35
  • [ 3279-95-6 ]
  • [ 156423-11-9 ]
  • 5-[bis-(2-chloro-ethyl)-amino]-<i>N</i>-(2-hydroxy-ethoxy)-2,4-dinitro-benzamide [ No CAS ]
 

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Technical Information

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