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Chemical Structure| 939-97-9 Chemical Structure| 939-97-9

Structure of 939-97-9

Chemical Structure| 939-97-9

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Product Details of [ 939-97-9 ]

CAS No. :939-97-9
Formula : C11H14O
M.W : 162.23
SMILES Code : O=CC1=CC=C(C(C)(C)C)C=C1
MDL No. :MFCD00035742
InChI Key :OTXINXDGSUFPNU-UHFFFAOYSA-N
Pubchem ID :70324

Safety of [ 939-97-9 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H360-H302-H317-H410
Precautionary Statements:P201-P202-P261-P264-P270-P272-P273-P280-P301+P310+P330-P302+P352-P308+P313-P333+P313-P391-P405-P501
Class:9
UN#:3082
Packing Group:

Computational Chemistry of [ 939-97-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.36
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 51.1
TPSA ?

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

17.07 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.18
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

2.84
Log Po/w (WLOGP)?

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

2.8
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.

2.69
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

3.17
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.73

Water Solubility

Log S (ESOL):?

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

-2.87
Solubility 0.217 mg/ml ; 0.00134 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.

-2.86
Solubility 0.226 mg/ml ; 0.00139 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

-3.54
Solubility 0.0463 mg/ml ; 0.000285 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

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.

-5.27 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)

1.0

Application In Synthesis of [ 939-97-9 ]

* 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 [ 939-97-9 ]

[ 939-97-9 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 939-97-9 ]
  • [ 120-35-4 ]
  • 3-(4-tert-Butyl-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 232 3-(4-tert-Butyl-benzylamino)-4-methoxy-N-phenyl-benzamide The title compound has been made using the procedure of Example 50, but using 3-amino-4-methoxy-N-phenyl benzamide and 4-tert-butylbenzaldehyde as starting materials, which are commercially available from Aldrich; m.p. 195-197 C.
  • 2
  • [ 939-97-9 ]
  • [ 28785-06-0 ]
  • [ 1186022-31-0 ]
  • 3
  • [ 939-97-9 ]
  • [ 2899-28-7 ]
  • [ 1227610-57-2 ]
  • [ 1227610-56-1 ]
  • 4
  • [ 939-97-9 ]
  • [ 57508-48-2 ]
  • [ 126-81-8 ]
  • ethyl 4-(4-t-butylphenyl)-2-amino-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With sodium ethanolate; In ethanol; at 80℃; for 0.833333h; General procedure: In a round bottom flask 1 eq. of dimedone, 1 eq of the desired aldehyde and 1 eq of <strong>[57508-48-2]ethyl 3-amino-3-iminopropionate hydrochloride</strong> were suspended in dry EtOH (2.5 mL/mmol) and heated at 80 C. To this solution 1 eq of a 0.5 M sodium ethanolate solution was added over the period of 20 min. After heating for further 30 min under reflux the reaction was cooled to 0 C and water (40 mL/mmol) was added. The aqueous solution was extracted with EtOAc (5×20 mL/mmol). The combined organic layers were washed with brine, dried with MgSO4 and the solvent was evaporated under reduced pressure. The crude material was purified by recrystallization from ethanol.
  • 5
  • [ 939-97-9 ]
  • [ 180683-64-1 ]
  • C22H36N2O2 [ No CAS ]
  • 6
  • [ 19063-55-9 ]
  • [ 939-97-9 ]
  • 6-bromo-3-[4-(tert-butyl)benzoyl]-2H-chromen-2-one [ No CAS ]
  • 7
  • [ 939-97-9 ]
  • [ 5369-19-7 ]
  • 4-(tert-butyl)-N-(3-(tert-butyl)phenyl)benzothioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Compound S1 was synthesized following a published procedure with slight modifications. 2Na2S·9H2O (1.5 g, 6.25 mmol) was added to a mixture of sulfur (1.0 g, 31.2 mmol) and3-(tert-butyl)aniline (5.6 g, 37.5 mmol) in DMF (25 mL). The suspension was stirred at 115 °C for0.5 h under nitrogen. Afterwards, the mixture was cooled to room temperature,4-(tert-butyl)benzaldehyde (4.1 g, 25 mmol) was added and the mixture was stirred at 115 °C for 24h under nitrogen. After cooling to room temperature, the resulting solution was quenched with saturated NH4Cl aqueous solution and extracted with ethyl acetate. The organic fraction was thoroughly washed with water and dried with Na2SO4. After concentration, the residue was purifiedby silica gel column (n-hexane/EtOAc = 40:1) to yield thioamide S1 as a yellow solid (4.72 g,58percent).1H NMR (300 MHz, CDCl3) delta 9.06 (brs, 1H), 7.83-7.76 (m, 3H), 7.72-7.62 (m, 1H), 7.51-7.27 (m,4H), 1.35 (s, 18H).13C NMR (75 MHz, CDCl3) delta 197.8, 154.7, 152.3, 140.6, 138.9, 128.5, 126.5, 125.5, 123.7, 120.6,120.5, 34.83, 34.78, 31.2, 31.1.IR (film): nu (cm1) 3173, 2957, 2867, 1595, 1512, 1472, 1419, 1336, 1274, 1240, 1199, 1112, 999,907, 843, 747, 701.HRMS (ESI, m/z) calcd for C21H27NSNa [M+Na]+: 348.1756, found: 348.1755.
  • 8
  • [ 939-97-9 ]
  • [ 5369-19-7 ]
  • 5-(tert-butyl)-2-(4-(tert-butyl)phenyl)benzo[d]thiazole [ No CAS ]
  • 9
  • [ 939-97-9 ]
  • [ 159152-14-4 ]
  • [ 128376-65-8 ]
  • C59H59BN4O2 [ No CAS ]
  • 10
  • [ 939-97-9 ]
  • [ 6882-68-4 ]
  • C26H36N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With sodium hydride; In tetrahydrofuran; at 35 - 80℃; for 8h; General procedure: Anhydrous tetrahydrofuran (50 mL) was added into a round-bottomed flask (100 mL) containing<strong>[6882-68-4]sophoridine</strong> (0.005 mol) and sodium hydride (0.1 mol). The solution was stirred, and aldehyde(0.02 mol) was added at 35-40 C. The solution was then refluxed for 8 h. After cooling to roomtemperature, the mixture was treated with hydrochloric acid (5%, 20 mL) to hydrolyze the excesssodium hydride and then extracted with chloroform (3 x 20 mL). The combined organic layer wasconcentrated, and the residue was purified in a reverse-phase silica gel column (CH2Cl2:MeOH = 20:1,v/v) to give compounds 2a-2k.
  • 11
  • [ 939-97-9 ]
  • [ 1986-47-6 ]
  • (1S*,2R*)-N-(4-(tert-butyl)benzyl)-2-phenylcyclopropan-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound.
  • 12
  • [ 939-97-9 ]
  • [ 19008-43-6 ]
  • C25H25NO2 [ No CAS ]
  • 13
  • [ 939-97-9 ]
  • [ 27757-86-4 ]
  • 5-(4-(tert-butyl)benzyl)-4,5-dihydro-6H-thieno[2,3-c]pyrrol-6-one [ No CAS ]
  • 14
  • [ 939-97-9 ]
  • [ 27757-86-4 ]
  • N-(4-(tert-butyl)benzyl)-1-(thiophen-3-yl)methanamine [ No CAS ]
  • 15
  • [ 939-97-9 ]
  • [ 19008-43-6 ]
  • benzyl 4-((4-(tert-butyl)benzyl)amino)benzoate [ No CAS ]
 

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