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Structure of 6940-80-3

Chemical Structure| 6940-80-3

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Product Details of [ 6940-80-3 ]

CAS No. :6940-80-3
Formula : C10H15NO
M.W : 165.23
SMILES Code : C[C@H](NCC1=CC=CC=C1)CO
MDL No. :MFCD03840382
InChI Key :PJXWCRXOPLGFLX-VIFPVBQESA-N
Pubchem ID :5356540

Safety of [ 6940-80-3 ]

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

Computational Chemistry of [ 6940-80-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.4
Num. rotatable bonds 4
Num. H-bond acceptors 2.0
Num. H-bond donors 2.0
Molar Refractivity 49.79
TPSA ?

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

32.26 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.29
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

1.28
Log Po/w (WLOGP)?

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

1.01
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.

1.56
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

1.74
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.57

Water Solubility

Log S (ESOL):?

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

-1.78
Solubility 2.76 mg/ml ; 0.0167 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.

-1.56
Solubility 4.58 mg/ml ; 0.0277 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

-3.11
Solubility 0.128 mg/ml ; 0.000776 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.

-6.4 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)

1.31

Application In Synthesis of [ 6940-80-3 ]

* 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 [ 6940-80-3 ]

[ 6940-80-3 ] Synthesis Path-Downstream   1~35

  • 2
  • [ 6940-80-3 ]
  • lysergic acid-azide; hydrochloride [ No CAS ]
  • [ 122764-74-3 ]
  • 4
  • [ 3217-09-2 ]
  • [ 6940-80-3 ]
  • 6
  • [ 7585-47-9 ]
  • [ 6940-80-3 ]
  • 7
  • [ 2749-11-3 ]
  • [ 100-52-7 ]
  • [ 6940-80-3 ]
YieldReaction ConditionsOperation in experiment
60% Step 1: (S)-Alininol (17.5 g, 233 mmol), PhCHO (26 g), and MgSO4 (70 g) were taken up in DCM and stirred at 25 0C for 19 h. The solution was filtered and concentrated which furnished a yellow solid. The residue was taken up in MeOH and cooled to O 0C. Sodium borohydride (11 g, 288 mmol) was added in portions to the solution at 0 0C (gas evolution). After the addition, the solution was stirred at 25 0C for 18 h. The solution was concentrated, and the residue was quenched carefully with 3 M HCI (aq.) (gas evolution/exotherm). The aqueous acidic layer was extracted with Et2O (4 X 200 ml_). The aqueous layer was cooled to 0 0C and made basic via addition of NaOH pellets (pH = 11 -12). The aqueous layer was extracted with DCM. The combined DCM layers were dried (MgSO4). Filtration and concentration gave 23.2 g (60percent) of the amino-alcohol as a white solid.
Preparation 11; Sodium triacetoxyborohydride (36.7 g) was added portion wisely to a mixture of (2S)-2-amino-1-propanol (10.0 g) and benzaldehyde (13.53 ml) in a mixture of dichloromethane (140 ml) and acetic acid (8.38 ml) at 0° C. and the whole was stirred at room temperature overnight. The mixture was washed successively with 2N sodium hydroxide and brine, and dried over sodium sulfate. The solution was evaporated under reduced pressure and the resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (30:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2S)-2-benzylamino-1-propanol (15.96 g). IR (KBr): 2843, 1496, 1454, 1377, 1340, 1065 cm-1 NMR (CDCl3, delta): 1.10 (3H, d, J=6.4 Hz), 2.77-2.93 (1H, m), 3.28 (1H, dd, J=10.6 and 6.9 Hz), 3.61 (1H, dd, J=10.6 and 4.0 Hz), 3.75, 3.87 (2H, ABq, J=13 Hz), 7.21-7.34 (5H, m) MASS (API-ES): 166 (M+H)+
With hydrogen;5% Pd(II)/C(eggshell); In ethanol; at 20℃; for 8h; [Preparation 6]: Synthesis of Compound 6(1) Optically-Active Compound of 2-benzylaminopropan-1-olTo a solution of (S)-(+)-2-aminopropan-1-ol (50.0 g) and benzaldehyde (74 ml) in ethanol (500 ml) was added 5percent palladium carbon (5.0 g), and the mixture was hydrogenated at room temperature under ordinary pressure for 8 hours. The reaction mixture was filtered through Celite, and concentrated under reduced pressure to give the titled compound (111.2 g).1H-NMR (DMSO-D6) delta: 7.34-7.27 (4H, m), 7.23-7.18 (1H, m), 4.53-4.47 (1H, m), 3.76 (1H, d, J=13.5 Hz), 3.66 (1H, d, J=13.5 Hz), 3.29-3.24 (2H, m), 2.65-2.55 (1H, m), 1.99 (1H, br s), 0.93 (3H, d, J=6.4 Hz).
  • 8
  • [ 56-41-7 ]
  • [ 100-52-7 ]
  • [ 6940-80-3 ]
  • 9
  • [ 6940-80-3 ]
  • [ 96-32-2 ]
  • [ 118460-11-0 ]
  • 10
  • [ 6940-80-3 ]
  • [ 106-95-6 ]
  • [ 148759-63-1 ]
  • 11
  • [ 6940-80-3 ]
  • [ 79-04-9 ]
  • [ 118948-07-5 ]
YieldReaction ConditionsOperation in experiment
95% With triethylamine; In dichloromethane; at 0 - 20℃; Step-5: N-Benzyl-2-chloro-N-((S)-2-hydroxy-1-methyl-ethyl)-acetamide To a solution of (S)-2-Benzylamino-propan-1-ol (4.1 g, 0.025 mol) in DCM was added triethylamine (3.8 ml, 0.028 mol) and chloroacetyl chloride (1.97 ml, 0.025 mol) at 0° C. The solution was stirred for 2 h at room temperature. The reaction mixture was concentrated and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated to afford 560 mg (95percent) of N-Benzyl-2-chloro-N-((S)-2-hydroxy-1-methyl-ethyl)-acetamide. LC/MS [M+H]+: 242.2
  • 12
  • [ 6940-80-3 ]
  • [ 598-21-0 ]
  • N-Benzyl-2-bromo-N-((S)-2-hydroxy-1-methyl-ethyl)-acetamide [ No CAS ]
  • 13
  • [ 6940-80-3 ]
  • [ 78-94-4 ]
  • [ 167905-80-8 ]
  • 14
  • [ 37746-78-4 ]
  • [ 6940-80-3 ]
  • ethyl (S)-(+)-5-benzyl-7-hydroxy-6-methyl-5-aza-2-heptenoate [ No CAS ]
  • 15
  • [ 6940-80-3 ]
  • [ 563-47-3 ]
  • (S)-(+)-3-benzyl-2,5-dimethyl-3-aza-5-hexen-1-ol [ No CAS ]
  • 16
  • [ 50-00-0 ]
  • [ 6940-80-3 ]
  • (S)-2-(Benzyl-hydroxymethyl-amino)-propan-1-ol [ No CAS ]
  • 17
  • [ 6940-80-3 ]
  • [ 1521-51-3 ]
  • (2S,3'R/S)-2-[N-benzyl-(cyclohexen-3'-yl)amino]propan-1-ol [ No CAS ]
  • 18
  • [ 6940-80-3 ]
  • [ 185849-99-4 ]
  • [ 185850-13-9 ]
  • (S)-2-(benzyl-{2-[1-(toluene-4-sulfonyl)-1H-imidazol-4-yl]-ethyl}-amino)-propan-1-ol [ No CAS ]
  • 19
  • [ 6940-80-3 ]
  • [ 90838-45-2 ]
  • [ 214911-98-5 ]
  • 20
  • [ 4801-15-4 ]
  • [ 6940-80-3 ]
  • [ 221876-44-4 ]
  • 22
  • [ 6940-80-3 ]
  • [ 67812-33-3 ]
  • [ 250137-68-9 ]
  • 23
  • [ 6940-80-3 ]
  • (+/-)-(R,S)-2,3-di-O-isopropylidenetartaric acid monomethyl ester [ No CAS ]
  • [ 250137-72-5 ]
  • 24
  • [ 6940-80-3 ]
  • N-benzyl-N-(2-chloro-1-methylethyl)amine hydrochloride [ No CAS ]
  • 25
  • [ 6940-80-3 ]
  • [ 4392-24-9 ]
  • [ 221876-43-3 ]
  • 26
  • [ 6940-80-3 ]
  • [ 17435-72-2 ]
  • [ 172034-96-7 ]
  • 29
  • bis(tetraethylammonium) carbonate [ No CAS ]
  • [ 458560-71-9 ]
  • [ 6940-80-3 ]
  • 31
  • [ 7585-47-9 ]
  • [ 6940-80-3 ]
  • 32
  • [ 6940-80-3 ]
  • N-benzyl-2-bromo-1-methylethylammonium bromide [ No CAS ]
  • 33
  • [ 6940-80-3 ]
  • Trifluoro-methanesulfonate(S)-1-((S)-2-[(S)-2-(allyl-benzyl-amino)-propyl]-benzyl-amino}-3-phenyl-propyl)-1-benzyl-2-isopropyl-aziridinium; [ No CAS ]
  • [ 717127-96-3 ]
  • 34
  • [ 5292-43-3 ]
  • [ 6940-80-3 ]
  • [ 873197-15-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 19.8333h; (2) Optically-Active Compound of [benzyl-(2-hydroxy-1-methylethyl)-amino]acetic acid tert-butyl esterTo a mixture of an optically-active compound of 2-benzylaminopropan-1-ol (111.2 g), potassium carbonate (111.6 g) and N,N-dimethylformamide (556 ml) cooled to 0° C. was added dropwise bromoacetic acid tert-butyl ester (109 ml) over 20 minutes, and the mixture was stirred at room temperature for 19.5 hours. The mixture was acidified by the addition of 2M aqueous hydrochloric acid solution and 6M aqueous hydrochloric acid solution to pH 2, and washed with toluene (1000 ml). The separated organic layer was extracted with 0.1M aqueous hydrochloric acid solution (300 ml). The combined aqueous layer was adjusted to pH 10 by 4M aqueous sodium hydroxide solution, and extracted with ethyl acetate (700 ml). The organic layer was sequentially washed with water (900 ml) and saturated aqueous sodium chloride solution (500 ml). The separated aqueous layer was extracted with ethyl acetate (400 ml) again. The combined organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the titled compound (160.0 g).1H-NMR (DMSO-D6) delta: 7.37-7.26 (4H, m), 7.24-7.19 (1H, m), 4.26 (1H, dd, J=6.9, 3.9 Hz), 3.76 (1H, d, J=14.1 Hz), 3.68 (1H, d, J=13.9 Hz), 3.45-3.39 (1H, m), 3.29-3.20 (1H, m), 3.24 (1H, d, J=17.2 Hz), 3.13 (1H, d, J=17.0 Hz), 2.84-2.74 (1H, m), 1.37 (9H, s), 0.96 (3H, d, J=6.8 Hz).
With potassium carbonate; In water; toluene; at 65℃; for 21h;Inert atmosphere; S-BAPO [1] (35.0 g, 212 mmol) was added to water (175 mL) at room temperature under nitrogen atmosphere. To the resulting suspension were added toluene (53 mL) and potassium carbonate (32.2 g, 233 mmol) at room temperature. To the resulting solution was added dropwise TBBA (434.4 g, 223 mmol) at room temperature, and then the used dropping funnel was washed with toluene (17 mL) and the washings were added to the reaction mixture. The reaction mixture was stirred at 65°C for 21 hours, and then cooled to room temperature. After toluene (105 mL) was added to the reaction mixture and then the mixture was stirred, the organic layer was separated out. The organic layer was washed with water (175 mL), aqueous layer was removed, and then the solvent was removed out of the organic layer in vacuo. Toluene (105 mL) was added to the residue and the toluene solution was concentrated. The operation was repeated two more times to give a toluene solution of S-BBMO [2] (74.0 g, 212 mmol in theory). The given toluene solution of S-BBMO was used in the next step, assuming that the yield was 100 percent. A crude product of S-BBMO which was prepared by the same process was evaporated to dryness and then measured about NMR and MS. 1H-NMR (DMSO-d 6) delta: 7.36-7.13 (5H, m), 4.26 (1H, dd, J = 6.8, 3.9 Hz), 3.72 (2H, dd, J = 14.2, 6.8 Hz), 3.47-3.38 (1H, m), 3.30-3.08 (3H, m), 2.79 (1H, sext, J = 6.8 Hz), 1.35 (9H, s), 0.96 (3H, d, J = 6.8 Hz). MS: m/z = 280 [M+H] +
With potassium carbonate; In water; toluene; at 65℃; for 21h;Inert atmosphere; 5-HAPO [1] (35.0 g, 212 mmol) was added to water (175 mE) at room temperature under nitrogen atmosphere. To the resulting suspension were added toluene (53 mE) and potassium carbonate (32.2 g, 233 mmol) at room temperature. To the resulting solution was added dropwise THEA (434.4 g, 223 mmol) at room temperature, and then a dropping thnnel used was washed with toluene (17 mE) and the washings were added to the reaction mixture. The reaction mixture was stirred at 65° C. for 21 hours, and then cooled to room temperature. Afier toluene (105 mE) was added to the reaction mixture and then the mixture was stirred, the organic layer was separated out. The organic layer was washed with water (175 mE), aqueous layer was removed, and then the solvent was removed out of the organic layer in vacuo. Toluene (105 mE) was added to the residue and the toluene solution was concentrated. The operation was repeated two more times to give a toluene solution of 5-HEMO [21(74.0 g, 212 mmol in theory). The given toluene solution of 5-HEMO was used in the next step, assuming that the yield was 100percent. A crude product of 5-HEMO which was prepared by the same process was evaporated to dryness and then measured about NMR and MS. ?H-NMR (DMSO-d5) oe: 7.36-7.13 (5H, m), 4.26 (1H, dd, J=6.8, 3.9 Hz), 3.72 (2H, dd, J=14.2, 6.8 Hz), 3.47-3.38 (1H, m), 3.30-3.08 (3H, m), 2.79 (1H, sext, J=6.8 Hz), 1.35 (9H, s), 0.96 (3H, d, J=6.8 Hz).10256] MS: mlz=280 [M+H]
  • 35
  • [ 6940-80-3 ]
  • [ 90238-20-3 ]
  • (S)-N-benzyl-N-(2-fluoro-1-methylethyl)benzamide [ No CAS ]
 

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