[ CAS No. 95517-07-0 ]

Name: 95517-07-0|1-(1-Hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone|95%
Brand: Ambeed
SKU: A863020
Rating: 97 (35 reviews)

{[proInfo.proName]} ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 95517-07-0

Structure of 95517-07-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 100K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 95517-07-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 95517-07-0 ]

SDS Specification

Alternatived Products of [ 95517-07-0 ]

Product Details of [ 95517-07-0 ]

CAS No. :	95517-07-0	MDL No. :	MFCD06658289
Formula :	C₁₂H₁₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NZAVQJCDRYONGJ-UHFFFAOYSA-N
M.W :	190.24 g/mol	Pubchem ID :	12065103
Synonyms :

Calculated chemistry of [ 95517-07-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.09
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.2 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.23
Log Po/w (XLOGP3) :	3.18
Log Po/w (WLOGP) :	2.47
Log Po/w (MLOGP) :	1.92
Log Po/w (SILICOS-IT) :	3.17
Consensus Log Po/w :	2.59

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.27
Solubility :	0.101 mg/ml ; 0.000532 mol/l
Class :	Soluble
Log S (Ali) :	-3.63
Solubility :	0.0441 mg/ml ; 0.000232 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.27
Solubility :	0.102 mg/ml ; 0.000538 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.86

Safety of [ 95517-07-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 95517-07-0 ]

* 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 [ 95517-07-0 ]

[ 95517-07-0 ] Synthesis Path-Downstream 1~23

1
[ 91028-13-6 ]
[ 95517-07-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With aluminium trichloride In 1,2-dichloro-benzene at 80℃; for 12h;
	With aluminium trichloride at 120℃;

2
[ 95517-07-0 ]
[ 98-88-4 ]
[ 861069-03-6 ]

Reference： [1]O'Farrell et al. [Journal of the Chemical Society, 1955, p. 3986,3992]

3
[ 570-08-1 ]
[ 78-27-3 ]
[ 95517-07-0 ]

Reference： [1]Lacey,R.N. [Journal of the Chemical Society, 1960, p. 3153 - 3160]

4
[ 529-35-1 ]
[ 75-36-5 ]
[ 95517-07-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 5,6,7,8-Tetrahydronaphthalen-1-ol With titanium tetrachloride at 20℃; Stage #2: acetyl chloride at 20 - 120℃; for 1.25h;

Reference： [1]Bensari, Ahlem; Zaveri, Nurulain T. [Synthesis, 2003, # 2, p. 267 - 271]

5
[ 95517-07-0 ]
[ 100-39-0 ]
[ 913721-70-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; tetrabutylammomium bromide In dichloromethane at 20℃; for 24h;
100%	With potassium carbonate In acetonitrile at 76℃; for 74h;	1.1a la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone ( 1 ) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity.
100%	With potassium carbonate In acetonitrile at 76℃; for 74h;	1.1a 1a) Synthesis of 1-(5-benzyloxytetralin-6-yl)ethanone (1) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity.

100%	With potassium carbonate In acetonitrile at 76℃; for 74h;	1.1a 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. (0082) Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity.
100%	In acetonitrile at 76℃; for 74h;	1.a la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone (1) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity.
100%	With potassium carbonate In acetonitrile at 76℃; for 74h;	1.1a la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone (1) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity.
100%	With potassium carbonate In acetonitrile at 76℃; for 122h;	1.a la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone (1) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (BOO imL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity.
	With potassium carbonate In acetonitrile at 76℃; for 48h;	1.1a 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated.Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity.

Reference： [1]Pallavicini, Marco; Budriesi, Roberta; Fumagalli, Laura; Ioan, Pierfranco; Chiarini, Alberto; Bolchi, Cristiano; Ugenti, Maria Paola; Colleoni, Simona; Gobbi, Marco; Valoti, Ermanno [Journal of Medicinal Chemistry, 2006, vol. 49, # 24, p. 7140 - 7149]
[2]Current Patent Assignee: POXEL - WO2021/37702, 2021, A1 Location in patent: Page/Page column 14; 15
[3]Current Patent Assignee: POXEL - WO2021/198284, 2021, A1 Location in patent: Page/Page column 12; 13
[4]Current Patent Assignee: POXEL - WO2021/204755, 2021, A1 Location in patent: Page/Page column 15
[5]Current Patent Assignee: POXEL - WO2021/198506, 2021, A1 Location in patent: Page/Page column 18
[6]Current Patent Assignee: POXEL - WO2021/191435, 2021, A1 Location in patent: Page/Page column 18-19
[7]Current Patent Assignee: POXEL - WO2021/198099, 2021, A1 Location in patent: Page/Page column 13
[8]Current Patent Assignee: POXEL - WO2021/204751, 2021, A1 Location in patent: Page/Page column 14; 15

6
[ 529-35-1 ]
[ 95517-07-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 100 percent / pyridine / CH₂Cl₂ / 3 h 2: 100 percent / aluminum chloride / 1,2-dichloro-benzene / 12 h / 80 °C

7
[ 95517-07-0 ]
2-phenyl-7,8,9,10-tetrahydro-benzo[<i>h</i>]chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 2: KOH; pyridine 3: acetic acid; aqueous hydrochloric acid

Reference： [1]O'Farrell et al. [Journal of the Chemical Society, 1955, p. 3986,3992]

8
[ 95517-07-0 ]
[ 857236-46-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 2: KOH; pyridine

Reference： [1]O'Farrell et al. [Journal of the Chemical Society, 1955, p. 3986,3992]

9
[ 95517-07-0 ]
[ 1779-49-3 ]
[ 1610359-63-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 1-(1-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere;
58%	Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 1-(1-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)ethan-1-one In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere;

Reference： [1]Seoane, Andrés; Casanova, Noelia; Quiñones, Noelia; Mascareñas, José L.; Gulías, Moisés [Journal of the American Chemical Society, 2014, vol. 136, # 21, p. 7607 - 7610]
[2]Gulías, Moisés; Marcos-Atanes, Daniel; Mascareñas, José L.; Font, Marc [Organic Process Research and Development, 2019, vol. 23, # 8, p. 1669 - 1673]

10
[ 95517-07-0 ]
[ 24350-15-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere 1.2: 72 h / 0 - 20 °C / Inert atmosphere 2.1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate monohydrate / acetonitrile / 16 h / 85 °C

Reference： [1]Gulías, Moisés; Marcos-Atanes, Daniel; Mascareñas, José L.; Font, Marc [Organic Process Research and Development, 2019, vol. 23, # 8, p. 1669 - 1673]

Yield	Reaction Conditions	Operation in experiment
83%	With aluminum (III) chloride at 135℃; for 1h;	20 General procedure: To a flask containing 2,3-dimethylphenyl acetate (1.85 g, 1 1.27 mmol, 1.0 eq.), AlC (1.73 g, 16.90 mmol, 1.5 eq.) was added portionwise. The reaction was continued at 135°C for 1 h. The resulting solid was then hydrolyzed with a mixture of ice and diluted HCI aqueous solution and extracted with AcOEt three times. Organic layers were combined, washed with diluted NaOH aqueous solution, dried, filtered off and concentrated in vacuo. The oily residue was purified by FCC (SiHP, Hexane: AcOEt 4:1) to afford the title compound (1.40 g, 8.53 mmol, yield 76%) as a white solid. ESI-MS: 165 [M+H]+ 1H NMR (300 MHz, DMSO-ofe) d 12.71 (s, 1H), 7.68 (d, J= 8.2 Hz, 1H), 6.80 (d, J= 8.2 Hz, 1H), 2.61 (s, 3H), 2.28 (s, 3H), 2.09 (s, 3H).

12
[ 95517-07-0 ]
ethyl 4-(5-benzyloxytetralin-6-yl)-5-chloro-2-[(2-phenylacetyl)amino]thiophene-3 -carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / 0 °C 3.2: 3 h / 0 - 20 °C

	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: POXEL - WO2020/99678, 2020, A1
[2]Current Patent Assignee: POXEL - WO2021/37702, 2021, A1
[3]Current Patent Assignee: POXEL - WO2021/198284, 2021, A1
[4]Current Patent Assignee: POXEL - WO2021/204751, 2021, A1
[5]Current Patent Assignee: POXEL - WO2021/204755, 2021, A1
[6]Current Patent Assignee: POXEL - WO2021/198506, 2021, A1
[7]Current Patent Assignee: POXEL - WO2021/198099, 2021, A1

13
[ 95517-07-0 ]
3-(5-benzyloxytetralin-6-yl)-2-chloro-4-hydroxy-5-phenyl-7H-thieno[2.3-b]pyridin-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / -16 - 20 °C
	Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C
	Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / 0 °C 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 4.2: 0 - 5 °C

	Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C
	Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C
	Multi-step reaction with 4 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C
	Multi-step reaction with 4 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C

14
[ 95517-07-0 ]
2-chloro-4-hydroxy-3-(5-hydroxytetralin-6-yl)-5-phenyl-7H-thieno[2,3-b]pyridin-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C
	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / 0 °C 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 4.2: 0 - 5 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C
	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C

	Multi-step reaction with 5 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 5.2: Cooling with ice
	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C

Reference： [1]Current Patent Assignee: POXEL - WO2020/99678, 2020, A1
[2]Current Patent Assignee: POXEL - WO2021/198284, 2021, A1
[3]Current Patent Assignee: POXEL - WO2021/204755, 2021, A1
[4]Current Patent Assignee: POXEL - WO2021/198506, 2021, A1
[5]Current Patent Assignee: POXEL - WO2021/198099, 2021, A1

15
[ 95517-07-0 ]
[ 1523493-78-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 6.1: potassium carbonate / acetic acid butyl ester; water / 0.58 h / 100 °C
	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 5.2: 50 - 80 °C
	Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / 0 °C 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 4.2: 0 - 5 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 6.1: potassium carbonate / water; isopropyl alcohol / 50 - 80 °C / pH Ca_. 8 - 12

	Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 5.2: 3 h / 50 °C / pH Ca_. 12
	Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 6.1: potassium carbonate / isopropyl alcohol; water / 3 h / 50 - 80 °C / pH Ca_. 8 - Ca_. 12
	Multi-step reaction with 6 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 5.2: Cooling with ice 6.1: potassium carbonate / isopropyl alcohol; water / 3 h / 50 - 80 °C / pH 8 - 12
	Multi-step reaction with 6 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C 3.1: N-chloro-succinimide / dichloromethane / 1 h / Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 1.08 h / -16 - 20 °C 5.1: boron trichloride / dichloromethane / 15 h / -15 - 20 °C 6.1: potassium carbonate / isopropyl alcohol; water / 3 h / 50 °C / pH Ca_. 8 - Ca_. 12

16
[ 95517-07-0 ]
ethyl 2-amino-4-(5-benzyloxytetralin-6-yl)thiophene-3-carboxylate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C

Reference： [1]Current Patent Assignee: POXEL - WO2020/99678, 2020, A1
[2]Current Patent Assignee: POXEL - WO2021/204755, 2021, A1

17
[ 95517-07-0 ]
[ 100-39-0 ]
l-(5-benzyloxytetralin-6-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In acetonitrile at 76℃; for 48h;	1.1a Example 1: Synthesis of the monohydrate potassium salt of formula (I) la) Synthesis of l-(5-benzyloxytetralin-6-yl)ethanone ( 1 ) 6-Acetyl-5-hydroxytetralin (100 g, 1 eq.) was dissolved in acetonitrile (300 mL). After addition of K2CO3 (1.1 eq.) and benzyl bromide (1.05 eq.), the suspension was heated (76°C). After 48 hours, benzyl bromide (0.1 eq) was added. After overall 74 hours, the solid was filtered off and washed with acetonitrile (200 mL), and the combined filtrates were evaporated. (0168) Compound 1 was obtained as a syrup: m = 148.6 g, quantitative yield, 96.6% a/a purity.

Reference： [1]Current Patent Assignee: POXEL - WO2020/99678, 2020, A1 Location in patent: Page/Page column 30

18
[ 95517-07-0 ]
ethyl 2-amino-4-(5-benzyloxytetralin-6-yl)thiophene-3-carboxylate hydrochloride salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 14 h / 20 °C
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 74 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 48 h / 76 °C 2.1: acetic acid; 1,1,1,3,3,3-hexamethyl-disilazane / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C

	Multi-step reaction with 2 steps 1.1: acetonitrile / 74 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C
	Multi-step reaction with 2 steps 1.1: potassium carbonate / acetonitrile / 122 h / 76 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; acetic acid / 24 h / 65 °C 2.2: 3 h / Reflux 2.3: 20 °C

Reference： [1]Current Patent Assignee: POXEL - WO2021/37702, 2021, A1
[2]Current Patent Assignee: POXEL - WO2021/198284, 2021, A1
[3]Current Patent Assignee: POXEL - WO2021/204751, 2021, A1
[4]Current Patent Assignee: POXEL - WO2021/198506, 2021, A1
[5]Current Patent Assignee: POXEL - WO2021/198099, 2021, A1

19
[ 95517-07-0 ]
4-isopropyl-6,7,8,9-tetrahydronaphtho[2,1-d]oxazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: tetrahydrofuran / 20 °C / Cooling with ice 2: triethylsilane; trifluoroacetic acid / dichloromethane / 0 - 20 °C 3: pyridine / dichloromethane / 0 - 20 °C 4: sodium azide / acetone / 12 h / 20 °C 5: C₁₉H₁₉Cl₃CoNO; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / 12 h / 60 °C / Sealed tube