[ CAS No. 37827-68-2 ] {[proInfo.proName]}

Name: 37827-68-2|7-Hydroxy-3,4-dihydro-1H-naphthalen-2-one|97%
Brand: Ambeed
SKU: A239794
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3d Animation Molecule Structure of 37827-68-2

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Quality Control of [ 37827-68-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 37827-68-2 ]

SDS Specification

Alternatived Products of [ 37827-68-2 ]

Product Details of [ 37827-68-2 ]

CAS No. :	37827-68-2	MDL No. :	MFCD04038657
Formula :	C₁₀H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LTLOEHIVHXTMBN-UHFFFAOYSA-N
M.W :	162.19	Pubchem ID :	4198875
Synonyms :

Calculated chemistry of [ 37827-68-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	46.1
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.48
Log Po/w (XLOGP3) :	1.25
Log Po/w (WLOGP) :	1.45
Log Po/w (MLOGP) :	1.35
Log Po/w (SILICOS-IT) :	2.52
Consensus Log Po/w :	1.61

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.0
Solubility :	1.61 mg/ml ; 0.00993 mol/l
Class :	Soluble
Log S (Ali) :	-1.63
Solubility :	3.79 mg/ml ; 0.0234 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.81
Solubility :	0.252 mg/ml ; 0.00155 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.76

Safety of [ 37827-68-2 ]

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 [ 37827-68-2 ]

* 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.

Upstream synthesis route of [ 37827-68-2 ]
Downstream synthetic route of [ 37827-68-2 ]

[ 37827-68-2 ] Synthesis Path-Upstream 1~7

1
[ 530-93-8 ]
[ 35697-10-0 ]
[ 52727-28-3 ]
[ 53568-05-1 ]
[ 37827-68-2 ]

Reference： [1] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098
[2] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098

2
[ 4133-34-0 ]
[ 108-98-5 ]
[ 37827-68-2 ]

Reference： [1] Patent: WO2004/80968, 2004, A1, . Location in patent: Page 46

3
[ 582-17-2 ]
[ 37827-68-2 ]

Reference： [1] Russian Journal of Organic Chemistry, 2000, vol. 36, # 10, p. 1474 - 1477

4
[ 208932-51-8 ]
[ 18107-18-1 ]
[ 37827-68-2 ]

Reference： [1] Tetrahedron, 2000, vol. 56, # 30, p. 5353 - 5361

5
[ 4133-34-0 ]
[ 37827-68-2 ]

Reference： [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 11, p. 2643 - 2646

6
[ 530-93-8 ]
[ 35697-10-0 ]
[ 52727-28-3 ]
[ 53568-05-1 ]
[ 37827-68-2 ]

Reference： [1] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098
[2] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3095 - 3098

7
[ 66628-99-7 ]
[ 37827-68-2 ]

Reference： [1] Tetrahedron, 2000, vol. 56, # 30, p. 5353 - 5361

[ 37827-68-2 ] Synthesis Path-Downstream 1~27

1
[ 37827-68-2 ]
[ 23484-71-1 ]
[ 38205-20-8 ]

Reference： [1]Journal of medicinal chemistry,1972,vol. 15,p. 1123 - 1128

2
[ 10599-17-4 ]
[ 37827-68-2 ]
[ 84344-52-5 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 435 - 439

3
[ 530-93-8 ]
[ 35697-10-0 ]
[ 52727-28-3 ]
[ 53568-05-1 ]
[ 37827-68-2 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 3095 - 3098
[2]Tetrahedron Letters,1983,vol. 24,p. 3095 - 3098

5
[ 208932-51-8 ]
[ 18107-18-1 ]
[ 37827-68-2 ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 5353 - 5361

6
[ 582-17-2 ]
[ 37827-68-2 ]

Reference： [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 1474 - 1477

7
[ 501-97-3 ]
potash [ No CAS ]
[ 37827-68-2 ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 5353 - 5361

8
[ 66628-99-7 ]
[ 37827-68-2 ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 5353 - 5361

9
[ 4133-34-0 ]
[ 108-98-5 ]
[ 37827-68-2 ]

Yield	Reaction Conditions	Operation in experiment
		Combine 7-methoxy-2-tetralone (5.00 g, 28.3 mmol), thiophenol (3.39 g, 30.8 mmol), K2CO3 (213 mg, 1.54 mmol), and NMP (15 ml) in a round bottom flask equipped with nitrogen inlet. Heat at 180C for six hours and then stir at ambient temperature overnight. Treat reaction mixture with 1N aq. NaOH (20 ml) and water (20 ml) before extracting with Et2O. Adjust the alkaline mixture to pH 4 with 1N aq. HCl and extract with Et2O(3x). Dry (MgSO4) the ethereal layer and concentrate to a yellow solid. Purify the crude material on silica gel, eluting with 5% EtOAc/DCM, to obtain 7-hydroxy-2-tetralone (1.88 g) as a light red solid. 1HNMR (CDCl3): 7.09 (d, 1H), 6.69 (d, 1H), 6.62 (s, 1H), 4.86 (s, 1H), 3.53 (s, 2H), 2.99 (t, 2H), 2.54 (t, 2H). Using a method similar to Example A, using 7-hydroxy-2-tetralone (1.88 g, 11.6 mmol), 6-chloronicotinamide (1.81 g, 11.6 mmol) and K2C03 (2,40 g, 17.4 mmol) gives the title compound (742 mg), after purification on silica gel (30% THF / DCM), as an amber foam. Mass spectrum (ion spray): mlz 283 (M+1); 1HNMR (DMSO-d6): 8.57 (s, 1H), 8.23 (d, 1H), 8.01 (s, 1H), 7.46 (s, 1H), 7.30 (d, 2H), 7.05 (d, 1H), 6.96 (m, 2H), 3.59 (s, 2H), 3.02 (t, 2H), 2.45 (t, 2H).

Reference： [1]Patent: WO2004/80968,2004,A1 .Location in patent: Page 46

10
[ 60-35-5 ]
[ 37827-68-2 ]
[ 1246770-37-5 ]

Reference： [1]Tetrahedron Asymmetry,2010,vol. 21,p. 1382 - 1388

11
[ 37827-68-2 ]
[ 77287-34-4 ]
[ 1246770-41-1 ]

Reference： [1]Tetrahedron Asymmetry,2010,vol. 21,p. 1382 - 1388

12
[ 358-23-6 ]
[ 37827-68-2 ]
[ 1355592-32-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 0.5h;	Step 1: 7-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate Intermediate 26 To a solution of <strong>[37827-68-2]7-hydroxy-3,4-dihydronaphthalen-2(1H)-one</strong> (3.82 g, 23.6 mmol) in DCM (100 mL) and 2,6-lutidine (3.27 mL, 28.3 mmol) at 0 C. was added trifluoromethanesulfonic anhydride (4.76 mL, 28.3 mmol) drop-wise. The reaction mixture was stirred at 0 C. for 30 min, and then allowed to warm to rt. After 30 min, the reaction mixture was diluted with DCM and washed with 1N HCl and then brine. The organic phase was dried over Na2SO4 and evaporated. The residue was purified by silica gel chromatography (7% to 30% EtOAc/hexane) to afford 7-oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (5.96 g, 86%). NMR (400 MHz, CDCl3) delta ppm 7.32 (d, J=8.3 Hz, 1H), 7.14 (dd, J=8.3, 2.6 Hz, 1H), 7.06 (d, J=2.5 Hz, 1H), 3.62 (s, 2H), 3.10 (t, J=6.7 Hz, 2H), 2.60-2.56 (m, 2H).

Reference： [1]Patent: US2012/15943,2012,A1 .Location in patent: Page/Page column 57

13
[ 4133-34-0 ]
[ 37827-68-2 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2643 - 2646

14
[ 37827-68-2 ]
[ 303185-87-7 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2643 - 2646
[2]Biocatalysis and Biotransformation,2012,vol. 30,p. 226 - 237

15
[ 37827-68-2 ]
[ 1374428-88-2 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2643 - 2646

16
[ 37827-68-2 ]
[ 1374428-94-0 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2643 - 2646

17
[ 37827-68-2 ]
[ 303185-87-7 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2643 - 2646

18
[ 37827-68-2 ]
[ 303185-87-7 ]
[ 303185-87-7 ]

Reference： [1]Biocatalysis and Biotransformation,2012,vol. 30,p. 226 - 237

19
[ 37827-68-2 ]
[ 7585-39-9 ]
C₁₀H₁₀O₂*C₄₂H₇₀O₃₅ [ No CAS ]

Reference： [1]Biocatalysis and Biotransformation,2012,vol. 30,p. 226 - 237

20
[ 37827-68-2 ]
3-((7-((2,6-dichlorobenzyl)oxy)-1,2,3,4-tetrahydronaphthalen-2-yl)amino)propanoic acid [ No CAS ]

Reference： [1]Patent: US2017/174672,2017,A1

21
[ 37827-68-2 ]
7-((2,6-dichlorobenzyl)oxy)-1,2,3,4-tetrahydronaphthalen-2-amine [ No CAS ]

Reference： [1]Patent: US2017/174672,2017,A1

22
[ 37827-68-2 ]
tert-butyl 3-((7-((2,6-dichlorobenzyl)oxy)-1,2,3,4-tetrahydronaphthalen-2-yl)amino)propanoate [ No CAS ]

Reference： [1]Patent: US2017/174672,2017,A1

23
[ 37827-68-2 ]
[ 20443-98-5 ]
7-((2,6-dichlorobenzyl)oxy)-3,4-dihydronaphthalen-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 20℃; for 2h;Inert atmosphere;	10.1 7-((2,6-dichlorobenzyl)oxy)-3,4-dihydronaphthalen-2(1H)-one 7-Hydroxy-tetralone (200 mg, 1.233 mmol) in DMF (1 ml) at 0 C. under Argon was mixed with potassium tert-butoxide (1.6M in THF, 0.925 ml, 1.480 mmol) and stirred for 1 h. 2-(bromomethyl)-1,3-dichlorobenzene (325 mg, 1.356 mmol) was added and the reaction mixture was stirred for 2 h, allowing the temperature to warm up to RT. The mixture was poured into cold 0.5M HCL and extracted with EtOAc. The combined organic layers were washed with water, dried over Na2SO4 filtered. After evaporation of the solvent a brown oil (559 mg) was obtained which was used without further purification.

Reference： [1]Patent: US2017/174672,2017,A1 .Location in patent: Paragraph 0752

24
[ 37827-68-2 ]
[ 41363-00-2 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium tetrahydroborate; ammonium acetate; In methanol; at 25℃;	To a solution of <strong>[37827-68-2]7-hydroxytetralin-2-one</strong> (500 mg, 3.08 mmol, 1 eq) in anhydrous MeOH (5 mL) was added NH4OAc (7.13 g, 92.49 mmol, 30 eq). After stirring for 5 h, NaBH4 (349.88 mg, 9.25 mmol, 3 eq) was added. The mixture was stirred at 25 C for 3 h. The mixture was concentrated to remove the solvent. H2O (10 mL) was added, the mixture was extracted with EtOAc (20 mL x 2). The aqueous was adjusted by 3 N HC1 to pH = 6-7, extracted with EtOAc (10 mL x 2). The aqueous was adjusted by 1 N NaOH to pH = 6-7. Then the mixture was lyophilized to give the solid. The solid was dissolved in z'-PrOH (10 mL). The resulting mixture was filtered and concentrated to give 3-aminotetralin-6-ol (550 mg, 2.66 mmol, 86.4% yield, 79.0% purity) as a yellow oil which was used in the next step without further purification. MR (400 MHz, CD3OD) delta ppm 6.91 (d, J = 8.2 Hz, 1H), 6.58 (dd, J = 2.4, 8.4 Hz, 1H), 6.51 (s, 1H), 3.53-3.42 (m, 1H), 3.06 (dd, J = 5.4, 15.5 Hz, 1H), 2.89-2.73 (m, 3H), 2.17 (d, J = 10.1Hz, 1H), 1.84-1.74 (m, 1H); ES-LCMS m/z 164.3 [M+H].

Reference： [1]Patent: WO2018/195397,2018,A2 .Location in patent: Paragraph 00644-00645

25
[ 37827-68-2 ]
3-[[5-(5-fluoro-3-pyridyl)-3-isopropylpyrazolo[1,5-a]pyrimidin-7-yl]amino]tetralin-6-ol [ No CAS ]

Reference： [1]Patent: WO2018/195397,2018,A2

26
[ 37827-68-2 ]
(3S)-3-[[5-(5-fluoro-3-pyridyl)-3-isopropylpyrazolo[1,5-a]pyrimidin-7-yl]amino]tetralin-6-ol [ No CAS ]
(3R)-3-[[5-(5-fluoro-3-pyridyl)-3-isopropylpyrazolo[1,5-a]pyrimidin-7-yl]amino]tetralin-6-ol [ No CAS ]

Reference： [1]Patent: WO2018/195397,2018,A2

27
[ 6342-56-9 ]
[ 37827-68-2 ]
3-methylnaphtho[2,3-b]furan-7-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: beta-tetralone 26 (100 mg, 0.68 mmol) was dissolved in dry CH2Cl2 (12 ml) and cooled to -35 C. A solution of TiCl4 (0.11 ml, 1.0 mmol) in CH2Cl2 (1 ml) followed by a solution of tributylamine (0.48 ml, 2.04 mmol) in dichloromethane (1.5 ml) were added sequentially. The reaction mixture was stirred for 30 minutes, a solution of 1,1-dimethoxyacetone (0.16 ml, 1.36 mmol) in CH2Cl2 (2 ml) was added and the reaction mixture was allowed to stir for 2 hours at room temperature. After completion of reaction, water (15 ml) was added and extraction was done with diethyl ether (2 x 15 ml). Combined organic layer was washed with bine (25 ml), dried over sodium sulphate (2 g) and evaporated to dryness under reduced pressure. Column chromatography was done with ethylacetate/hexanes (5:95). The product was obtained as a gummy liquid in 92% (114 mg).

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 1122 - 1125

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 37827-68-2 ] {[proInfo.proName]}

Quality Control of [ 37827-68-2 ]

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[ 37827-68-2 ] Synthesis Path-Upstream 1~7

[ 37827-68-2 ] Synthesis Path-Downstream 1~27

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Aryls

Ketones

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[ 37827-68-2 ]