[ CAS No. 1270294-05-7 ]

Name: 1270294-05-7|(R)-5,7-Difluorochroman-4-ol|97%
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SKU: A488822
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3d Animation Molecule Structure of 1270294-05-7

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Quality Control of [ 1270294-05-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1270294-05-7 ]

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Alternatived Products of [ 1270294-05-7 ]

Product Details of [ 1270294-05-7 ]

CAS No. :	1270294-05-7	MDL No. :	MFCD09763634
Formula :	C₉H₈F₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	186.16 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 1270294-05-7 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	41.67
TPSA :	29.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	1.37
Log Po/w (WLOGP) :	2.3
Log Po/w (MLOGP) :	1.98
Log Po/w (SILICOS-IT) :	2.63
Consensus Log Po/w :	2.07

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.2
Solubility :	1.18 mg/ml ; 0.00633 mol/l
Class :	Soluble
Log S (Ali) :	-1.59
Solubility :	4.77 mg/ml ; 0.0256 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.72
Solubility :	0.353 mg/ml ; 0.0019 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.58

Safety of [ 1270294-05-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1270294-05-7 ]

* 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 [ 1270294-05-7 ]

[ 1270294-05-7 ] Synthesis Path-Downstream 1~8

1
[ 844648-22-2 ]
[ 1270294-05-7 ]

Yield	Reaction Conditions	Operation in experiment
66.5%	With dimethylsulfide borane complex; (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol In tetrahydrofuran; toluene at 20℃; for 5.5h; Inert atmosphere;	2 Preparation of (R)-5,7-difluorochroman-4-ol (5) Take a 1L three-necked flask, add anhydrous THF (66mL) and S-Me-CBS (1mol/L toluene solution, 9mL, 9mmol), protect with argon, and inject borane dimethyl sulfide complex at room temperature (10mol/L, 9.9mL, 99mmol). Dissolve 5,7-difluorochroman-4-one (16.6 g, 90 mmol) in anhydrous tetrahydrofuran (166 mL) and slowly drip into the above system. The entire dripping process lasted 5.5 hours. After dripping, let it stand overnight. The reaction solution was slowly poured into methanol cooled in an ice-water bath to generate a large number of bubbles, stirred until no obvious bubbles were generated, and concentrated to remove the solvent. Add 100 mL of ethyl acetate to dissolve, wash the organic phase with water (50 mL, 30 mL) and brine (20 mL) successively, dry over anhydrous sodium sulfate, filter, and concentrate to obtain an oil, which is placed at room temperature as a yellow solid. The chiral purity measured by chiral HPLC was 93.6%ee (OZ-H column, n-hexane/isopropanol=95/5, flow rate=1mL/min, detection wavelength 220nm). The above solid was heated and dissolved in a mixed solvent consisting of n-hexane and ethyl acetate (n-hexane/ethyl acetate=17:1), and 11.1 g of needle crystals were obtained by recrystallization, with a yield of 66.5%. [α] D20 = +141.9 (c = 1, MeOH). The chiral purity measured by chiral HPLC is >99.9%ee (OZ-H column, n-hexane/isopropanol=95/5, flow rate=1 mL/min, detection wavelength 220nm).
	Multi-step reaction with 3 steps 1: sodium tetrahydridoborate; methanol / 1 h / 0 °C 2: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 3: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C
	Multi-step reaction with 4 steps 1: sodium tetrahydridoborate; methanol / 1 h / 0 °C 2: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 4: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A Location in patent: Paragraph 0133-0138
[2]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A
[3]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A

2
[ 1270294-05-7 ]
[ 2648486-31-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A

3
[ 1270294-05-7 ]
[ 2648486-32-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr 3: sodium acetate / dichloromethane / 1 h
	Multi-step reaction with 3 steps 1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr 3: sodium acetate / dichloromethane / 24 h / 20 °C

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A
[2]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A

4
[ 1270294-05-7 ]
[ 942195-55-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr 3.1: sodium acetate / dichloromethane / 1 h 4.1: N-chloro-succinimide / acetonitrile / 0.58 h / 5 °C 4.2: 2 h / 20 °C
	Multi-step reaction with 4 steps 1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 5 h / Inert atmosphere; Cooling with ice 2.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran; water / 3 h / 1292.9 Torr 3.1: sodium acetate / dichloromethane / 24 h / 20 °C 4.1: N-chloro-succinimide / acetonitrile / 0.58 h / 5 °C 4.2: 2 h / 20 °C

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A
[2]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A

5
[ 1369878-15-8 ]
[ 1270294-05-7 ]
[ 2648486-30-8 ]

Yield	Reaction Conditions	Operation in experiment
89.7%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 5h; Inert atmosphere; Cooling with ice;	8-9 (S)-3-((5,7-Difluorochroman-4-yl)oxy)-N,N-dimethyl-4-nitrobenzamide (6) Compound 4 (210mg, 1mmol), compound 5 (186mg, 1mmol), triphenylphosphine (314 mg, 1.2mmol) were dissolved in anhydrous THF (5mL), protected by argon, cooled in an ice water bath, and then DIAD ( A mixed solution consisting of 236 μL, 1.2 mmol) and anhydrous THF (0.3 mL) was dripped and stirred for 5 hours. Concentrate and purify by silica gel column chromatography (0-2% ethyl acetate in dichloromethane solution). Compound 6 was obtained, with a total of 339 mg of off-white solid, with a yield of 89.7%.

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF MEDICAL SCIENCES - CN112851646, 2021, A Location in patent: Paragraph 0163-0170

6
[ 2820178-15-0 ]
[ 1270294-05-7 ]

Yield	Reaction Conditions	Operation in experiment
92.4%	With methanol; sodium tetrahydridoborate; lithium hydroxide monohydrate at 20℃; for 1h;	1.S4 ((R)-5,7-difluorochroman-4-yl)4-nitrobenzoate (A-5) (2.26 g, 6.7 mmol) was added to 20 mL of methanol, and sodium hydroxide ( 0.6g, 15mmol), water 10mL, stirred at room temperature for 1h, and monitored the reaction progress by thin-layer chromatography until the reaction was complete; concentrated and evaporated most of the methanol, adjusted the pH to 7 with 1N hydrochloric acid, precipitated a solid, suction filtered, washed with water, 50 Drying at gave (R)-5,7-difluorochroman-4-ol (III) 1.16 g of a near-white solid with a yield of 92.4%.

Reference： [1]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A Location in patent: Paragraph 0042; 0054

7
[ 917248-51-2 ]
[ 1270294-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C
	Multi-step reaction with 3 steps 1: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 3: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C

Reference： [1]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A
[2]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A

8
[ 2820178-14-9 ]
[ 1270294-05-7 ]

Yield	Reaction Conditions	Operation in experiment
93.4%	With methanol; sodium tetrahydridoborate; lithium hydroxide monohydrate at 20℃; for 1h;	1.S3 S3: add (R)-5,7-difluorochroman-4-ol acetate (A-3) (1.8 g, 7.9 mmol) prepared in step S2 into 20 mL of methanol, add sodium hydroxide (0.7 g, 17.5 mmol), 10 mL of water, stirred at room temperature for 1 h, and monitored the reaction progress by thin-layer chromatography until the reaction was complete; concentrated and evaporated most of the methanol, adjusted the pH to 7 with 1N hydrochloric acid, and precipitated a solid, suction filtered, washed with water, 50 Drying at gave (R)-5,7-difluorochroman-4-ol (III) 1.37 g of a near-white solid with a yield of 93.4%.

Reference： [1]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN114907303, 2022, A Location in patent: Paragraph 0042; 0049-0052

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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. 1270294-05-7 ]

Quality Control of [ 1270294-05-7 ]

Related Doc. of [ 1270294-05-7 ]

Product Details of [ 1270294-05-7 ]

Calculated chemistry of of [ 1270294-05-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1270294-05-7 ]

Application In Synthesis of [ 1270294-05-7 ]

[ 1270294-05-7 ] Synthesis Path-Downstream 1~8

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry