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Structure of 35150-09-5

Chemical Structure| 35150-09-5

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Product Details of [ 35150-09-5 ]

CAS No. :35150-09-5
Formula : C7H14N2O3
M.W : 174.20
SMILES Code : CC(C)(C)OC(=O)NCC(N)=O
MDL No. :MFCD08275106
InChI Key :RHONTQZNLFIDCQ-UHFFFAOYSA-N
Pubchem ID :10910064

Safety of [ 35150-09-5 ]

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

Computational Chemistry of [ 35150-09-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.71
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 43.18
TPSA ?

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

81.42 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.6
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

-0.13
Log Po/w (WLOGP)?

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

0.0
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.

-0.23
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

-0.63
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.12

Water Solubility

Log S (ESOL):?

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

-0.51
Solubility 54.1 mg/ml ; 0.31 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.

-1.13
Solubility 13.0 mg/ml ; 0.0748 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

-0.82
Solubility 26.2 mg/ml ; 0.151 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.

-7.45 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)

1.96

Application In Synthesis of [ 35150-09-5 ]

* 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 [ 35150-09-5 ]

[ 35150-09-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 35150-09-5 ]
  • [ 89226-13-1 ]
YieldReaction ConditionsOperation in experiment
100% With Lawessons reagent; In tetrahydrofuran; at 20℃; for 16h; To compound 386 (21.63 g, 0.124 mol) dissolved in THF (400 mL) was added Lawesson reagent (30.13 g, 0.074 mol). Stirred at room temperature for 16 h then concentrated. Purified by silica gel chromatography (eluant: 3% MeOH- CH2CI2) then re-purified by silica gel chromatography (eluant: 2% MeOH- CH2Cl2) to give 23.59 g (100%) of the product 387 as a light green solid. MS m/e: 135 (M+2-tBu). For n=2: MS m/e: 149 (M+2-tBu)
78% With Lawessons reagent; In tetrahydrofuran; at 20℃; for 24h; Carbamoylmethyl-carbamic acid tert-butyl ester (10.88 grams, 62.46 mmol) and Lawesson's Reagent (15.66 grams, 38.72 mmol) were dissolved in THF (200 ml) and stirred under a nitrogen atmosphere at ambient temperature for 24 hours. The solvent was removed and the residue purified by column chromatography on silica (20% EtOAc/ hexanes) to yield Compound 14.2 (9.21 grams, 48.41 mmol, 78%). IH NMR (400 MHz, DMSO-d6) delta ppm 1.36 (s, 9 H) 3.80 (m, 2 H) 7.03 (m, 1 H) 8.99 (m, 1 H) 9.66 (m, 1 H).
60% With Lawessons reagent; In dichloromethane; at 20℃; for 16h;Inert atmosphere; Lawesson?s reagent (893 mg, 4.25 mmol) was added to a solution of glycineamide (740 mg, 4.25 mmol) in dry CH2Cl2 (50 mL) and the reaction mixture was stirred under N2 atmosphere at room temperature for 16 h. The reaction was quenched by addition of saturated aqueous NaHCO3 and was stirred for 1 h before been extracted with EtOAc (3 x 15 mL). The organic layers were washed with brine (20 mL); dried with MgSO4 and the solvent evaporated under reduced pressure to give the crude product wich was purified by flash chromatography (hexane/ EtOAc, 1:1) to give 8 (466 mg, 60 %) as a white solid. Rf = 0.51 (hexane/ EtOAc, 1:1); 1H NMR (400MHz, CDCl3) delta 1.46 (s, 9H), 4.16 (d, 2H, J = 6.1 Hz), 5.33 (bs, 1H), 7.66 (bs, 1H), 7.89 (bs, 1H). 13C NMR (100MHz, CDCl3) delta 28.3 (3C), 51.4, 81.1, 156.4, 205.1.
51% With Lawessons reagent; In tetrahydrofuran; at 20℃;Inert atmosphere; To a solution of N-Boc-glycinamide (2.5 g, 14.3 mmol, 1 equiv.) in anhydrous THF (20 mL) was added Lawesson's reagent (3.5 g, 8.6 mmol, 1 equiv.) under argon. The reaction mixture was stirred at rt overnight. The solvent was evaporated and the residue purified by flash chromatography using EtOAc/CH2Cl2 (1/9) to give 5 as a white solid (1.4 g, 51%)
42% With Lawessons reagent; In dichloromethane; at 20℃; for 12h; To a solution of Boc-Gly-NH2 (11 g, 62.9 mmol) in CH2Cl2 (300 mL) was added Lawesson's Reagent (13.2 g, 32.7 mmol). After stirring at rt for 12 h, the mixture was concentrated. Purification of the residue (SiO2; 50% Et2O in hexanes) provided the desired product (5.0 g, 42%).
44 g With Lawessons reagent; In tetrahydrofuran; at 20℃; for 5h; Compound 23 (42.59g, 244 . 5mmol) dissolved in tetrahydrofuran (500 ml), cooled to 0 C, plus olausson reagent (59.34g, 146 . 7mmol), stirring at room temperature to 5h, decompression turns on lathe thf, the residue is poured into the ice and saturated sodium bicarbonate solution, ethyl acetate extraction of the organic phase (500mLx3), combined with the phase, the organic phase with saturated salt water washing, dry anhydrous sodium sulfate, concentrated, the residue is dissolved in silica gel column chromatography to obtain white solid compound 24 (44g, 95%). 1 HNMR (400MHz, CDCl 3): delta 7.82 (br, 1H), 7.52 (br, 1H), 5.25 (br, 1H), 4.16 (d, J= 6.0Hz, 2H), 1.46 (s, 9H).

 

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