172366-38-0|5,7-Difluoro-3,4-dihydronaphthalen-2(1H)-one| Ambeed

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Quality Control of [ 172366-38-0 ] Purity: 95% SDS Specification

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Product Details of [ 172366-38-0 ]

CAS No. :	172366-38-0
Formula :	C₁₀H₈F₂O
M.W :	182.17
SMILES Code :	O=C1CC2=C(C(F)=CC(F)=C2)CC1
MDL No. :	MFCD03788446
InChI Key :	HOUVATQQKYAEBB-UHFFFAOYSA-N
Pubchem ID :	3635758

Safety of [ 172366-38-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 172366-38-0 ]

* 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 [ 172366-38-0 ]

[ 172366-38-0 ] Synthesis Path-Downstream 1~33

1
[ 151-50-8 ]
[ 172366-38-0 ]
[ 1025943-63-8 ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4056 - 4069.

2
[ 74-85-1 ]
[ 105184-38-1 ]
[ 172366-38-0 ]

Yield	Reaction Conditions	Operation in experiment
80%		(1) Dissolve 100 grams of 3,5-difluorophenylacetic acid 1 in 500 mL of dichloromethane,Add 50 grams of thionyl chloride under stirring, and then increase the temperature to 40~50,After keeping this temperature for 4 hours, the reaction is completed by HPLC and TLC.Cool down, concentrate, add dichloromethane to dilute and store temporarily, as the prepared acid chloride;Add 500 mL of dichloromethane to another reaction flask,Then add 150g aluminum trichloride,Then add the previously prepared acid chloride dropwise to the reaction system,After the addition is complete, ethylene gas is introduced into the system,When the reaction of the raw materials is complete, add 500 mL of purified water to the system to quench the reaction.After quenching, the system is separated and the organic phase is concentrated.Intermediate 2 was obtained by column chromatography with a yield of 80%;
	aluminium trichloride; In dichloromethane;	(Example 4) Synthesis of 6,8-difluoro-2-propyl-7-(3,4,5-trifluorophenyl)-9,10-dihydrophenanthrene Following conversion of (3,5-difluorophenyl)-acetic acid to an acid chloride with thionyl chloride, subsequent reaction with ethylene gas at -10C using methylene chloride as the solvent and in the presence of aluminum chloride yielded 5,7-difluoro-3,4-dihydro-1H-naphthalen-2-one.
	aluminium trichloride; In dichloromethane;	Following conversion of (3,5-difluorophenyl)-acetic acid to an acid chloride with thionyl chloride, subsequent reaction with ethylene gas at -10C using methylene chloride as the solvent and in the presence of aluminum chloride yielded 5,7-difluoro-3,4-dihydro-1H-naphthalen-2-one.

References: [1]Patent: CN113527108,2021,A .Location in patent: Paragraph 0012; 0033; 0035-0036.
[2]Molecular Crystals and Liquid Crystals,2004,vol. 411,p. 155/[1197]-161/[1203].
[3]Patent: EP1201632,2002,A1 .
[4]Patent: EP1201632,2002,A1 .

3
[ 172366-38-0 ]
[ 1730-25-2 ]
5,7-difluoro-2-propyl-1,2,3,4-tetrahydro-naphthalene [ No CAS ]

References: [1]Molecular Crystals and Liquid Crystals,2004,vol. 411,p. 155/[1197]-161/[1203].

4
[ 172366-38-0 ]
5,7-difluoro-2-propyl-6-(3,4,5-trifluoro-phenyl)-1,2,3,4-tetrahydro-naphthalene [ No CAS ]

References: [1]Molecular Crystals and Liquid Crystals,2004,vol. 411,p. 155/[1197]-161/[1203].

5
[ 172366-38-0 ]
2-Aminomethyl-5,7-difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4056 - 4069.

6
[ 172366-38-0 ]
C₁₂H₁₂F₂N₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4056 - 4069.

7
[ 74-85-1 ]
[ 157033-24-4 ]
[ 172366-38-0 ]

Yield	Reaction Conditions	Operation in experiment
88%		dissolve 2.1 kg of intermediate II (1 equivalent) in 21 L of dichloroethane,After the dissolution is complete, slowly add 2.6 kg of aluminum trichloride (2 equivalents) to the resulting solution B, stir to dissolve the aluminum trichloride, and then reduce the temperature to below -10 C to obtain the reaction system A. Add sulfuric acid-dried ethylene gas to A, and test while adding ethylene gas, until no intermediate II is detected, stop adding ethylene gas, continue stirring at room temperature overnight, post-treatment to obtain 1.6kg of intermediate III as a tetraketone The structural formula is: In this step, the acid chloride is cyclized with aluminum trichloride in ethylene dichloride and ethylene to form intermediate III, and the reaction yield is 88%.
73.6 g		5,7-Difluoro-2-tetralone. SOCl2 (100 mL) was added in one portion to 3,5-difluorophenylacetic acid (100 g, 0.58 mol) and after stirring for 15 h, the volatiles were evaporated under reduced pressure. The resulting oily acid chloride was dissolved in CH2Cl2 (200 mL) and added dropwise to a mechanically stirred suspension of AlCl3 (154 g, 1.16 mol) in CH2Cl2 (1.0 L). The stirred suspension was cooled to an internal temperature of -65 C in a dry ice/acetone bath, and the acid chloride solution was added at such a rate in order to maintain an internal temperature <-60 C. After the addition was complete, ethylene gas was bubbled through the reaction mixture at a rapid rate for 10 min at -65 C. The reaction mixture was allowed to warm to 0 C over 2 h with stirring, and was then cooled to -10 C and treated with H2O (500 mL) initially dropwise, followed by rapid addition. The organic layer was separated, washed with brine (100 mL) and dried over MgSO4. Evaporation under reduced pressure gave a dark oily residue which was distilled in vacuo on a Kugelrohr collecting material boiling between 90-110 C (1.0 to 0.7 mm Hg). The distillate was redistilled at 100-105 C (0.3 mm Hg) to give the product as a white solid, (73.6 g, 0.40 mol; 70%): mp 46 C; IR (KBr) 1705 cm-1; 1H NMR (CDCl3) δ 2.55 (t, J =7.5 Hz, 2H), 3.10 (t, J = 7.5 Hz, 2H), 3.58 (s, 2H), 6.70 (m, 2H); MS m/z 182 (M+). Anal. Calcd for C10H8F2O: C, 65.93; H, 4.42. Found: C, 65.54; H, 4.42.

References: [1]Patent: CN111018663,2020,A .Location in patent: Paragraph 0012; 0014; 0020.
[2]Patent: EP1191008,2002,A1 .Location in patent: Page 68.
[3]Patent: EP2182804,2017,B1 .Location in patent: Paragraph 0130.

8
[ 866627-49-8 ]
[ 172366-38-0 ]
2-(S)-(5,7-difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-isopropylthiazol-2-yl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃; for 16.0h;	The 5, 7-difluoro-2-tetralone (0.3 mmol) was dissolved in 2.0 mL of anhydrous dichloromethane under N2 at rt. 2- (S)-Amino-pentanoic acid (5-isopropyl-thiazol-2-yl)-amide (0.3 mmol) was then added to the reaction solution, followed by sodium triacetoxy borohydride (0.3 mmol) and acetic acid (0.3 mmol). The reaction was stirred at rt for 16 h. The crude solution was then diluted with 20 mL of EtOAc and washed with 20 mL of aqueous 1N NaOH solution and brine. The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude products were purified through flash chromatography to give 2- (S)- (5, 7-Difluoro-1, 2,3, 4-tetrahydro-naphthalen-2-ylamino)- pentanoic acid (5-isopropyl-thiazol-2-yl)-amide. LC-MS (retention time, M+1) : 2.2 min, 408 [M+1]

References: [1]Patent: WO2005/95367,2005,A1 .Location in patent: Page/Page column 28-29.

Yield	Reaction Conditions	Operation in experiment
		A stirred suspension of aluminum chloride (154 g, 1.16 mmol) in 1 L of methylene chloride was cooled to -65 C. and the acid chloride in 200 mL of methylene chloride was added dropwise such that the reaction temperature did not exceed -60 C. Ethylene gas was bubbled through the suspension at a rapid rate for 10 minutes at -65 C. The reaction mixture was allowed to warm to 0 C. over 2 hours, then cooled to -10 C. and treated with 500 mL of water. The organic layer was separated, washed with 100 mL of aqueous sodium chloride, and then dried over magnesium sulfate. The mixture was filtered and the filtrate was concentrated under reduced pressure. Distillation of the residue in vacuo (bp 90-110 C. [1.0 to 0.7 mm]) gave a clear distillate. Redistillation (bp 100-105 C. [0.3 mm]) gave 5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-one (73.56 g, 0,342 mol) as a white solid, m.p. 46 C.

10
[ 588-93-2 ]
[ 172366-38-0 ]
C₁₉H₂₀F₂O [ No CAS ]

References: [1]Patent: EP1191008,2002,A1 .Location in patent: Page 68.

11
[ 37059-57-7 ]
(-)-1R,2S-N-methylephedrine [ No CAS ]
[ 172366-38-0 ]
(R)-(+)-2-hydroxy-5,7-difluoro-1,2,3,4-tetrahydronaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With hydrogenchloride; In diethyl ether; hexane;	(R)-(+)-2-Hydroxy-5,7-difluoro-1,2,3,4-tetrahydronaphthalene. A solution of (-)-1R,2S-N-methylephedrine (81.3 g, 0.454 mol) in anhydrous Et2O (1.1 L) was added dropwise (45 min) to 1.0 M lithium aluminum hydride (416 mL, 0.416 mol) in Et2O at a rate sufficient to maintain a gentle reflux. After the addition was complete, the reaction mixture was heated at reflux for 1 h then allowed to cool to room temperature. A solution of 2-ethylaminopyridine (111 g, 0.98 mole) in anhydrous Et2O (100 mL) was added (45 min) at such a rate as to maintain a gentle reflux. The reaction mixture was heated at reflux for a further 1 h, during which time a light yellow-green suspension appeared. The mixture was cooled to an internal temperature of -65 C. using a dry ice-acetone bath and a solution of <strong>[172366-38-0]5,7-difluoro-2-tetralone</strong> (23.0 g, 126 mmol) in Et2O (125 mL) was added dropwise at a rate maintaining the internal temperature below -60 C. After the addition was complete, the mixture was stirred at -65 C. to -68 C. for 3 h and quenched by the addition of MeOH (100 mL) maintaining the internal temperature below -60 C. The reaction was stirred for a further 10 min at -65 C. and allowed to warm to approximately -20 C. A solution of 3N HCl (2 L) was then added at a rate to limit the temperature to <35 C. After stirring at an increased rate to achieve total dissolution, the layers were separated and the ethereal layer was washed with brine (200 mL) and dried (MgSO4). The ethereal solution was evaporated under reduced pressure and the residue dissolved in warm Et2O (20 mL) followed by the addition of hexane (200 mL). The seeded solution was cooled in an ice bath and maintained at 0 C. for 1 h whereupon the resulting deposited crystals were collected and dried in vacuo to give the alcohol (10.9 g, 47%): mp 85 C.; [α]25D +38.1 (c=1.83, CHCl3); 93.4% ee by chiral HPLC: 1H NMR (CDCl3) δ 1.70 (br s, 1H), 1.76-1.88 (m, 2H), 1.99-2.06 (m, 2H), 2.63-3.08 (m, 3H), 4.15 (m, 1H), 6.60 (m, 2H). Anal. Calcd for C10H10F2O: C, 65.21; H, 5.47. Found: C, 65.38: H, 5.42. The spectra for the (S)-enantiomer 4b are identical: mp 84-85 C.; [α]25D -37.8 (c=1.24, CHCl3); 92.4% ee by chiral HPLC. Anal. Calcd for C10H10F2O: C, 65.21; H, 5.47. Found: C, 65.47; H, 5.39.

References: [1]Patent: US2009/41800,2009,A1 .

12
[ 105184-38-1 ]
[ 172366-38-0 ]

References: [1]Patent: EP2182804,2017,B1 .
[2]Patent: CN111018663,2020,A .

13
[ 172366-38-0 ]
(R)-(+)-2-hydroxy-5,7-difluoro-1,2,3,4-tetrahydronaphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With 2-(ethylamino)pyridine; lithium aluminium tetrahydride; (-)-N-methylephedrine; In diethyl ether; at -68 - -60℃; for 3.0h;	(R)-(+)-2-Hydroxy-5,7-difluoro-1,2,3,4-tetrahydronaphthalene. A solution of (-)-1R,2S-N-methylephedrine (81.3 g, 0.454 mol) in anhydrous Et2O (1.1 L) was added dropwise (45 min) to 1.0 M lithium aluminum hydride (416 mL, 0.416 mol) in Et2O at a rate sufficient to maintain a gentle reflux. After the addition was complete, the reaction mixture was heated at reflux for 1 h then allowed to cool to room temperature. A solution of 2-ethylaminopyridine (111 g, 0.98 mole) in anhydrous Et2O (100 mL) was added (45 min) at such a rate as to maintain a gentle reflux. The reaction mixture was heated at reflux for a further 1 h, during which time a light yellow-green suspension appeared. The mixture was cooled to an internal temperature of -65 C using a dry ice-acetone bath and a solution of <strong>[172366-38-0]5,7-difluoro-2-tetralone</strong> (23.0 g, 126 mmol) in Et2O (125 mL) was added dropwise at a rate maintaining the internal temperature below -60 C. After the addition was complete, the mixture was stirred at -65 C to -68 C for 3 h and quenched by the addition of MeOH (100 mL) maintaining the internal temperature below -60 C. The reaction was stirred for a further 10 min at -65 C and allowed to warm to approximately -20 C. A solution of 3N HCl (2 L) was then added at a rate to limit the temperature to <35 C. After stirring at an increased rate to achieve total dissolution, the layers were separated and the ethereal layer was washed with brine (200 mL) and dried (MgSO4) The ethereal solution was evaporated under reduced pressure and the residue dissolved in warm Et2O (20 mL) followed by the addition of hexane (200 mL). The seeded solution was cooled in an ice bath and maintained at 0 C for 1 h whereupon the resulting deposited crystals were collected and dried in vacuo to give the alcohol (10.9 g, 47 %): mp 85 C; [α]25D +38.1 (c = 1.83, CHCl3); 93.4% ee by chiral HPLC: 1H NMR (CDCl3) δ 1.70 (br s, 1H), 1.76-1.88 (m, 2H), 1.99-2.06 (m, 2H), 2.63-3.08 (m, 3H), 4.15 (m, 1H), 6.60 (m, 2H). Anal. Calcd for C10H10F2O: C, 65.21; H, 5.47. Found: C, 65.38: H, 5.42. The spectra for the (S)-enantiomer 4b are identical: mp 84-85 C; [α]25D -37.8 (c = 1.24, CHCl3); 92.4% ee by chiral HPLC. Anal. Calcd for C10H10F2O: C, 65.21; H, 5.47. Found: C, 65.47; H, 5.39.

References: [1]Patent: EP2182804,2017,B1 .Location in patent: Paragraph 0131.
[2]Patent: CN111018663,2020,A .

14
[ 172366-38-0 ]
(R)-(+)-2-methanesulfonyloxy-5,7-difluoro-1,2,3,4-tetrahydronaphthalene [ No CAS ]

References: [1]Patent: EP2182804,2017,B1 .

15
[ 172366-38-0 ]
C₁₀H₉F₂N₃ [ No CAS ]

References: [1]Patent: EP2182804,2017,B1 .

16
[ 172366-38-0 ]
(S)-(-)-2-amino-5,7-difluoro-1,2,3,4-tetrahydronaphthalene hydrochloride [ No CAS ]

References: [1]Patent: EP2182804,2017,B1 .
[2]Patent: CN113527108,2021,A .

17
[ 172366-38-0 ]
(S)-(-)-(5,7-difluoro-1,2,3,4-tetrahydronaphth-2-yl)(cyanomethyl)amine [ No CAS ]

References: [1]Patent: EP2182804,2017,B1 .

18
[ 172366-38-0 ]
[ 173996-22-0 ]

Yield	Reaction Conditions	Operation in experiment
96.3%	With sodium tetrahydroborate; In methanol; for 5.0h;Large scale;	Dissolve 1.6 kg of intermediate III (1 equivalent) in 16 L of methanol. After the dissolution is complete, add 0.34 kg of sodium borohydride (1 equivalent) to the resulting solution C to obtain reaction system B After the temperature of the reaction system B rises slightly, let the reaction system B react for 5 hours. After the reaction is terminated, the reaction system B after the reaction is quenched. After the treatment, 1.56 kg of intermediate IV is obtained. Its structural formula is: In the step, the ketone is reduced by sodium borohydride in methanol to obtain intermediate IV, and the reaction yield is 96.3%.

References: [1]Patent: CN111018663,2020,A .Location in patent: Paragraph 0012; 0015; 0021.

19
[ 172366-38-0 ]
C₁₂H₁₂F₂O₂ [ No CAS ]

References: [1]Patent: CN111018663,2020,A .

20
[ 172366-38-0 ]
5,7-difluoronaphthalen-2-ol [ No CAS ]