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Structure of 161344-84-9

Chemical Structure| 161344-84-9

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Product Details of [ 161344-84-9 ]

CAS No. :161344-84-9
Formula : C12H23BN2O4
M.W : 270.13
SMILES Code : CCCCB1O[C@@H]([C@H](O1)C(=O)N(C)C)C(=O)N(C)C
MDL No. :MFCD05663838
InChI Key :AFQWQRBBIZKYTE-UWVGGRQHSA-N
Pubchem ID :10978509

Safety of [ 161344-84-9 ]

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

Computational Chemistry of [ 161344-84-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 19
Num. arom. heavy atoms 0
Fraction Csp3 0.83
Num. rotatable bonds 7
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 72.86
TPSA ?

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

59.08 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

0.93
Log Po/w (WLOGP)?

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

0.24
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.

-0.72
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

-1.03
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.

-1.64
Solubility 6.21 mg/ml ; 0.023 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.

-1.76
Solubility 4.73 mg/ml ; 0.0175 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

-1.21
Solubility 16.5 mg/ml ; 0.0611 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.

-7.29 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<0.0
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)

3.96

Application In Synthesis of [ 161344-84-9 ]

* 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 [ 161344-84-9 ]

[ 161344-84-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 74962-99-5 ]
  • [ 161344-84-9 ]
  • [ 339194-90-0 ]
  • [ 304856-32-4 ]
  • 2
  • [ 92527-13-4 ]
  • [ 63126-52-3 ]
  • [ 161344-84-9 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; water; at 20℃; for 1.0h; Example 26B; 2-Butyl-f 1.3.21dioxaborolane-(S.S)-4.5-dicarboxylic acid bis-dimethylamide; 2-(But-1-yl)-tetrahydro-4H-1,3,6,2-dioxazaborocine [CAS 92527-13-4] was prepared from n-butylboronic acid and 2-(2-hydroxy-ethylamino)-ethanol [CAS 111-42-2] as reported in Organic Synthesis, 1998, 76, 86-96. This dioxazaborocine (3 g, 17.5 mmol) and (2S,3S)-2,3-dihydroxy-N,N,N',N'- tetramethyl-butanediamide [CAS 63126-52-3] (4.65 g) were dissolved in anhydrous dichloromethane (95 ml.) under N2. Brine (30 ml_) was added. The resulting mixture was stirred at room temperature for 1 hour. The two layers were separated, and the aqueous layer was extracted with dichloromethane (30 ml_). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide the title compound as an oil. 1H NMR (300 MHz, CDCI3): delta 0.82-0.9 (m, 5H), 1.25-1.45 (m, 4H), 2.98 (s, 6H), 3.2 (s, 6H), 5.52 (S, 2H). MS (DCI-NH3) m/z 271 (M+H)+.
  • 3
  • ° molecular sieves powder [ No CAS ]
  • [ 263550-53-4 ]
  • [ 75-11-6 ]
  • [ 161344-84-9 ]
  • 4,4-dimethyl-6-[(1S,2S)-3-hydroxy-1,2-methano-1-methyl-propyl]-2-oxo-1-(2-propyl)-1,2,3,4-tetrahydroquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.41 g (91%) In hexane; dichloromethane; ethyl acetate; 4,4-Dimethyl-6-[(1S,2S)-3-hydroxy-1,2-methano-1-methyl-propyl]-2-oxo-1-(2-propyl)-1,2,3,4-tetrahydroquinoline Compound 11 To a stirred, cooled (-25 C.) solution of diethyl zinc in anhydrous dichloromethane (9.06 mL, 16.4 mmol) under argon, 1,2-dimethoxyethane (1.7 mL, 16.4 mmol) was added over 2 minutes followed by diiodomethane (2.7 mL, 32.8 mmol) at such a rate that the temperature of the cooling bath did not increase above -20 C. After the addition was complete, the reaction mixture was stirred for 5 minutes and then cannulated into a cooled (-25 C.), stirred solution of 4,4-dimethyl-6-(3-hydroxy-1-methyl-prop-1(Z)-enyl)-2-oxo-1-(2-propyl)-1,2,3,4-tetrahydroquinoline (Compound 9 0.43 g, 1.5 mmol), 4A molecular sieves powder (0.5 g) and (4S-trans)-2-butyl-N,N,N',N'-tetramethyl[1,3,2]dioxaborolane-[4,5]dicarboxamide (Compound 10) in 10 mL of anhydrous dichloromethane over 5 minutes. The slurry was stirred at -25+ C. for 1.5 hour, at -15 C. for 3 hours and at 0 C. for 3 hours. The reaction was quenched with 20 mL of saturated, aqueous ammonium chloride solution and extracted with dichloromethane (2*35 mL). The combined organic extract was dried over anhydrous sodium sulfate and the solvent evaporated to give a residue which on purification by flash column chromatography on silica gel (230-400 mesh) using 30% ethyl acetate in hexane as the eluent provided 0.41 g (91%) of the title compound as a pale yellow, viscous oil. 1 H-NMR (300 MHz, CDCl3):d 0.78-0.86(m, 2H), 1.20-1.30(m, 1H), 1.27(s, 6H), 1.39(s, 3H), 1.53(d, J=7.0 Hz, 6H), 2.40(s, 2H), 3.25(dq, J=11.4 Hz, 2H), 4.64(heptet, J=7.0 Hz, 1H), 7.04(d, J=8.4 Hz, 1H), 7.17(dd, J=8.3, 2.0 Hz, 1H), 7.22(d, J=2.0 Hz, 1H).
  • 4
  • [ 14399-53-2 ]
  • [ 74141-12-1 ]
  • [ 161344-84-9 ]
  • [ 89849-80-9 ]
  • 5
  • [ 82994-41-0 ]
  • [ 14399-53-2 ]
  • [ 161344-84-9 ]
  • [ 89849-80-9 ]
  • 6
  • [ 75-11-6 ]
  • [ 1192063-81-2 ]
  • [ 161344-84-9 ]
  • [ 1192063-83-4 ]
YieldReaction ConditionsOperation in experiment
Dichloromethane stabilized with EtOH was distilled from CaH2 under N2 and sparged with N2 to maintain oxygen free solvents.A 500 ml 3N round bottom flask was equipped with an addition funnel topped with a 3 way stopcock and internal thermal couple. The apparatus was evacuated and backfilled with N2 4 times. To this degassed vessel was added 20 mL DCM, Diethyl Ether (5.06 g, transferred by weight) and a solution OfEt2Zn (8.43 g, 68.2 mmol, in 30 ml DCM) under a N2 atmosphere. The solution was cooled to -20 C and a solution Of CH2I2 (36.5 g, 136 mmol, in 20 ml DCM) was added dropwise. The temperature is monitored with an internal temperature probe. The rate of addition was altered to maintain a constant -20 C internal temperature. A fine precipitate forms after the addition is -80% complete. The mixture was stirred for 10 minutes.A solution of the commercially available (S, S) dioxaborolane Hgand (7.37 g, 27.3 mmol) in DCM (20 mL) was added. The mixture was stirred for 10 minutes. The precipitate dissolves yielding a clear solution. A solution of the alkene from step 2 of this example (8.53 g, 22.7 mmol) in DCM (20 mL) was added. The solution was warmed to 0 C and stirred for 24 hours. The solution remains clear after stirring for 24 hours. The reaction was quenched after 24 hr by addition of 50 ml of sat'd aq. NH4Cl. The mixture was placed in a separatory funnel, 250 ml DCM and 200 ml 10 % HCl (aq) added, shaken, and the layers separated. The aqueous layer was re-extracted with DCM (2 x 150ml), the organic layers combined, transferred to a Morton flask. 2N NaOH (300 ml) and 50 ml of 30% H2O2 were added. The biphasic solution was stirred vigorously for 12 hours. The layers were separated and the aqueous phase was re-extracted with DCM (2 x 150ml), the organic phases were combined, washed with 10% HCl (aq, 250 ml), IN Na2S2O3 (250 ml), sat'd NaHCO3 (250 ml), brine (250 ml), dried over MgSO4, filtered and stripped. The material was purified by chromatography on SiO2 eluting with 30% EtOAc : Hexanes. The desired product is obtained as a mixture with the minor diastereomer and the residual SM. The desired diastereomer was isolated by chromatography on Chiralpak IA stationary phase.
  • 7
  • [ 4426-47-5 ]
  • (-)-N,N,N′,N′-tetramethyl-D-tartaric acid [ No CAS ]
  • [ 161344-84-9 ]
  • 8
  • [ 4426-47-5 ]
  • [ 63126-52-3 ]
  • [ 161344-84-9 ]
 

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Technical Information

Categories

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[ 161344-84-9 ]

Organoborons

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Amines

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Related Parent Nucleus of
[ 161344-84-9 ]

Other Aliphatic Heterocycles

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