146407-32-1|1-Benzylazepan-3-one| Ambeed

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Quality Control of [ 146407-32-1 ] Purity: 95% SDS Specification

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Product Details of [ 146407-32-1 ]

CAS No. :	146407-32-1
Formula :	C₁₃H₁₇NO
M.W :	203.28
SMILES Code :	O=C1CN(CC2=CC=CC=C2)CCCC1
MDL No. :	MFCD10568165
InChI Key :	HGWZSFXXGQVVAQ-UHFFFAOYSA-N
Pubchem ID :	15152264

Safety of [ 146407-32-1 ]

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

Computational Chemistry of [ 146407-32-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.46
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	65.15
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	20.31 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.33
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.02
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.71
Log P_o/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.	1.93
Log P_o/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	2.82
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.16

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.54
Solubility	0.59 mg/ml ; 0.0029 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.	-2.07
Solubility	1.71 mg/ml ; 0.00844 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	-3.7
Solubility	0.0407 mg/ml ; 0.0002 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.	-6.11 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	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)	1.34

Application In Synthesis of [ 146407-32-1 ]

* 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 [ 146407-32-1 ]

[ 146407-32-1 ] Synthesis Path-Downstream 1~29

1
[ 146407-32-1 ]
ε-caprolactam [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen;palladium(II) oxide; In methanol; water; at 20℃; under 3750.38 Torr;	13a Perhydro-azepin-3-oneTo 120 g (500 mmol) <strong>[146407-32-1]1-benzyl-perhydro-azepin-3-one</strong> in 800 mL MeOH and 100 mL water is added 12.0 g Pd(II)-O. The reaction mixture is stirred under a hydrogen atmosphere of 5000 hPa at RT overnight. The solvent is evaporated, the residue is co-evaporated twice with 100 mL toluene. The residue is elutriated with acetone. The precipitate is collected and dried. Yield: 73.5 g (98% of theory) <n="89"/>Melting point = 142CRf-value: 0.55 (silica gel, mixture H).

References: [1]Patent: WO2008/22979,2008,A1 .Location in patent: Page/Page column 87.

2
[ 478841-09-7 ]
[ 146407-32-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride; for 12h;Reflux; Inert atmosphere;	Compound 53-3 (18 g, 65.5 mmol) was added into HCl solution (6 mol/L, 180 mL) under nitrogen atmosphere, and the reaction solution was stirred at reflux for 12 h. After TLC indicated the reaction was complete, the reaction solution was cooled down to r.t. and adjusted to a pH greater than 9 with NaOH solution. The resulting solution was extracted with a mixture of DCM/MeOH (10/1) (200 mL×2). The organic phase was washed with saturated brine, dried over anhydrous Na2SO4, filtered and evaporated to give the title compound 53-4 (yellow oil, 11.9 g, Yield 89%). 1H NMR (400 MHz, d6-DMSO): delta ppm 7.38-7.27 (m, 5H), 3.72 (s, 2H), 3.27 (s, 2H), 2.76-2.71 (m, 4H), 1.75 (m, 4H)
	With sulfuric acid; In ethanol; water; at 120℃; for 12h;	Under a nitrogen atmosphere, a 75%-aqueous sulfuric acid solution (2 ml) was added to a solution of ethyl 1-benzyl-3-oxoazepane-4-carboxylate (150 mg, 0.545 mmol) in ethanol (1 ml) at room temperature, and the resulting mixture was heated to 120C. After 3 hours, completion of the reaction was confirmed and the resulting mixture was cooled. On the other hand, under a nitrogen atmosphere, a 75%-aqueous sulfuric acid solution (2 ml) was added to a solution of the mixture containing ethyl 1-benzyl-3-oxoazepane-2-carboxylate (200 mg, content = about 75%) in ethanol (1 ml) at room temperature, and the resulting mixture was heated to 120C. After 12 hours, completion of the reaction was confirmed and the temperature was lowered. The reaction solution was combined with that obtained above, and the combined reaction solution was poured onto ice and adjusted to pH 8 with a 2M-aqueous sodium hydroxide solution. The combined reaction solution thus treated was extracted with ethyl acetate (50 ml x 2) and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 1-benzylazepan-3-one (118.1 mg, 53%).

References: [1]Patent: US2017/313683,2017,A1 .Location in patent: Paragraph 1040-1041.
[2]Patent: EP1403255,2004,A1 .Location in patent: Page 146.

3
[ 146407-32-1 ]
[ 148473-84-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With lithium aluminium tetrahydride; In diethyl ether; at 20℃; for 0.5h;	Under a nitrogen atmosphere, lithium aluminum hydride (1.4 mg, 0.0369 mmol) was added to a solution of <strong>[146407-32-1]1-benzylazepan-3-one</strong> (15 mg, 0.0738 mmol) in diethyl ether (1 ml) at 0C, and the resulting mixture was heated to room temperature. After 30 minutes, water, a 2M-aqueous sodium hydroxide solution and water were added in that order to the reaction solution. The resulting mixture was filtered by the use of Celite, and the filtrate was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol) to obtain 1-benzylazepan-3-ol (16.2 mg, 100%).

References: [1]Patent: EP1403255,2004,A1 .Location in patent: Page 146-147.
[2]Process Biochemistry,2017,vol. 56,p. 90 - 97.

4
[ 478841-08-6 ]
[ 146407-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; In ethanol; water; at 120℃; for 3h;	Under a nitrogen atmosphere, a 75%-aqueous sulfuric acid solution (2 ml) was added to a solution of ethyl 1-benzyl-3-oxoazepane-4-carboxylate (150 mg, 0.545 mmol) in ethanol (1 ml) at room temperature, and the resulting mixture was heated to 120C. After 3 hours, completion of the reaction was confirmed and the resulting mixture was cooled. On the other hand, under a nitrogen atmosphere, a 75%-aqueous sulfuric acid solution (2 ml) was added to a solution of the mixture containing ethyl 1-benzyl-3-oxoazepane-2-carboxylate (200 mg, content = about 75%) in ethanol (1 ml) at room temperature, and the resulting mixture was heated to 120C. After 12 hours, completion of the reaction was confirmed and the temperature was lowered. The reaction solution was combined with that obtained above, and the combined reaction solution was poured onto ice and adjusted to pH 8 with a 2M-aqueous sodium hydroxide solution. The combined reaction solution thus treated was extracted with ethyl acetate (50 ml x 2) and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 1-benzylazepan-3-one (118.1 mg, 53%).

References: [1]Patent: EP1403255,2004,A1 .Location in patent: Page 146.

5
[ 765940-56-5 ]
[ 146407-32-1 ]

Yield	Reaction Conditions	Operation in experiment
45%		Eine Suspension von Kalium tert-Butylat (336 mg) in Toluol (2. 5 ml) wird waehrend 10 min am Rueckfluss gekocht. Anschliessend wird 5- (BENZYL-ETHOXYCARBONYLMETHYL-AMINO)- pentansaeure (695 mg) in Toluol (1 ml) langsam zur Suspension gegeben und nach beendeter Zugabe waehrend 1. 5 Stunden weiter gekocht. Nach Abkuehlen auf Raumtemperatur wird 25% Chlorwasserstoffsaeure (1 ml) zugegeben. Die organische Phase wird abgetrennt und mit 25% Chlorwasserstoffsaeure (4x 1 ml) gewaschen. Die vereinigten salzsauren waessrigen Phasen werden anschliessend waehrend 5 Stunden am Rueckfluss gekocht. Nach Abkuehlen auf Raumtemperatur wird die Loesung mit 2N Natronlauge basisch (pH 11) gestellt und mit Ethylacetat extrahiert. Die vereinigten organischen Phasen werden nach dem Trocknen ueber Natriumsulfat eingedampft. Der erhaltene Rueckstand ergibt nach Chromatographie an Kieselgel (Ethylacetat/ Heptane 1 : 5) und ergibt die gewuenschte Titelverbindung (197 mg) in 45 % Ausbeute (Bull. Chem. Soc. JPN. 1956, 29, 631- 632 ; DE2206385).

References: [1]Patent: WO2004/83218,2004,A1 .Location in patent: Page 58.

6
[ 867-13-0 ]
[ 146407-32-1 ]
ethyl (1-benzylazepane-3-ylidene)acetate [ No CAS ]
ethyl (1-benzylazepane-3-ylidene)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 2h;	Sodium hydride and <strong>[146407-32-1]1-benzylazepane-3-one</strong> were added to a THF solution of ethyl diethoxyphosphorylacetate under ice cooling and stirred for two hours at room temperature to give a stereoisomeric mixture of ethyl (1-benzylazepane-3-ylidene)acetate. After the obtained stereoisomeric mixture of ethyl (1-benzylazepane-3-ylidene)acetate was processed with 4M HCl-EtOAc solution, EtOH and 10% palladium carbon were added and stirred for 15 hours at room temperature under the hydrogen atmosphere to give ethyl azepane-3-ylacetate hydrochloride. MS: 186

References: [1]Patent: EP1806347,2007,A1 .Location in patent: Page/Page column 16.

7
[ 867-13-0 ]
[ 146407-32-1 ]
ethyl (1-benzylazepane-3-ylidene)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; ethanol; at 0 - 20℃; for 2h;	Reference Example 10 Sodium hydride and <strong>[146407-32-1]1-benzylazepan-3-one</strong> were added to a THF solution of ethyl diethoxyphosphorylacetate with ice-cooling, and the mixture was stirred at ambient temperature for 2 hours to yield a stereoisomeric mixture of ethyl (1-benylazepan-3-ylidene)acetate, which was treated with 4M HCl-EtOAc solution, followed by adding EtOH and 10% palladium on activated carbon and stirring under hydrogen atmosphere at ambient temperature for 15 hours to yield ethyl azepan-3-ylacetate hydrochloride. MS:186

References: [1]Patent: EP1803710,2007,A1 .Location in patent: Page/Page column 16.

8
[ 146407-32-1 ]
(S)-1-benzylazepan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With recombinant Rhodococcus erythropolis DSM 43297 ketoredutase; nicotinamide adenine dinucleotide; In aq. phosphate buffer; isopropyl alcohol; at 50℃; for 24h;pH 7.0;Enzymatic reaction;	General procedure: The reaction mixture containing 200 mM substrate, 1mM NAD+, 5% (v/v) 2-propanol and 10mg crude enzyme READH in 1mL potassium phosphate buffer (100mM, pH 7.0) was incubated at 50 C. For ChKRED20, 40% (v/v) 2-propanol and a reaction temperature of 40 C were applied instead. The reaction was monitored by TLC, and terminated by extracting with methyl tert-butyl ether (1 mL). The organic extract was dried over anhydrous sodium sulfate and concentrated. The samples were subjected to chiral HPLC to determine the conversion and enantiomeric excess. The products were purified by silica gel column chromatography, and identified by NMR analysis, optical rotation measurements and mass spectrometry.

References: [1]Process Biochemistry,2017,vol. 56,p. 90 - 97.

9
[ 146407-32-1 ]
(R)-1-benzylazepan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35.2 mg	With recombinant Chryseobacterium sp. CA 49 ketoreductase; nicotinamide adenine dinucleotide; In aq. phosphate buffer; isopropyl alcohol; at 40℃; for 24h;pH 7.0;Enzymatic reaction;	General procedure: The reaction mixture containing 200 mM substrate, 1mM NAD+, 5% (v/v) 2-propanol and 10mg crude enzyme READH in 1mL potassium phosphate buffer (100mM, pH 7.0) was incubated at 50 C. For ChKRED20, 40% (v/v) 2-propanol and a reaction temperature of 40 C were applied instead. The reaction was monitored by TLC, and terminated by extracting with methyl tert-butyl ether (1 mL). The organic extract was dried over anhydrous sodium sulfate and concentrated. The samples were subjected to chiral HPLC to determine the conversion and enantiomeric excess. The products were purified by silica gel column chromatography, and identified by NMR analysis, optical rotation measurements and mass spectrometry.

References: [1]Process Biochemistry,2017,vol. 56,p. 90 - 97.

10
[ 6436-90-4 ]
[ 146407-32-1 ]

References: [1]Patent: US2017/313683,2017,A1 .
[2]Patent: EP1403255,2004,A1 .
[3]Patent: EP1403255,2004,A1 .

11
[ 478841-07-5 ]
[ 146407-32-1 ]

References: [1]Patent: US2017/313683,2017,A1 .
[2]Patent: EP1403255,2004,A1 .
[3]Patent: EP1403255,2004,A1 .

12
[ 146407-32-1 ]
[ 478841-10-0 ]