[ CAS No. 105640-07-1 ] {[proInfo.proName]}

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2D 3D

Structure of 105640-07-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 105640-07-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 105640-07-1 ]

SDS Specification

Alternatived Products of [ 105640-07-1 ]

Product Details of [ 105640-07-1 ]

CAS No. :	105640-07-1	MDL No. :	MFCD00210693
Formula :	C₁₂H₁₄O₂	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	SLJYPZJZQIHNGU-UHFFFAOYSA-N
M.W :	190.24	Pubchem ID :	4598916
Synonyms :

Calculated chemistry of [ 105640-07-1 ] Expand+

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 :	55.55
TPSA :	37.3 ?2

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) :	-6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	1.94
Log Po/w (WLOGP) :	2.62
Log Po/w (MLOGP) :	1.92
Log Po/w (SILICOS-IT) :	2.83
Consensus Log Po/w :	2.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.49
Solubility :	0.612 mg/ml ; 0.00321 mol/l
Class :	Soluble
Log S (Ali) :	-2.35
Solubility :	0.854 mg/ml ; 0.00449 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.15
Solubility :	0.135 mg/ml ; 0.000708 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.37

Safety of [ 105640-07-1 ]

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

Application In Synthesis of [ 105640-07-1 ]

* 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.

Upstream synthesis route of [ 105640-07-1 ]
Downstream synthetic route of [ 105640-07-1 ]

[ 105640-07-1 ] Synthesis Path-Upstream 1~2

1
[ 92-88-6 ]
[ 20601-38-1 ]
[ 16715-88-1 ]
[ 105640-07-1 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 13, p. 3218 - 3221

2
[ 75-30-9 ]
[ 105640-07-1 ]
[ 365553-47-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In water; N,N-dimethyl-formamide	Step 1 A solution of 4-(4-hydroxyphenyl)cyclohexanone (6.0 g, 31.6 mmol) in DMF (90 mL) was treated with K₂CO₃ (21 g, 158 mmol, 5 equiv) and 2-iodopropane (15 mL, 26.8 g, 158 mmol, 5 equiv.). The reaction was heated at 100° C. overnight. After the solvent was removed, the residue was treated with H₂O and extracted with EtOAc. The organic extracts were combined and washed with brine, dried over Na₂SO₄ and concentrated in vacuum to give the spectroscopically pure 4-(4-isopropoxyphenyl)cyclohexanone (7.02 g, 95percent). ¹H NMR (CDCl₃): 7.14 (dt, 2H), 6.84 (dt, 2H), 4.3 (septet, 1H), 2.97 (tt, 1H), 2.46-2.52 (m, 4H), 2.16-2.24 (m, 2H), 1.83-1.98 (m, 2H) and 1.33 (d, 6H).

Reference： [1] Patent: US2002/143141, 2002, A1,
[2] Patent: US2001/56179, 2001, A1,

[ 105640-07-1 ] Synthesis Path-Downstream 1~4

1
[ 105640-07-1 ]
[ 75-03-6 ]
[ 163671-48-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In water; acetone;	EXAMPLE 3 Preparation of Fmoc-1-amino-4-(4-ethoxyphenyl)cyclohexane-1-carboxylic acid (Fmoc-4-EtOApc-OH) A solution of 4-(4-hydroxyphenyl)cyclohexanone (5.0 g, 26.3 mmol) in acetone (100 mL) was treated with K2CO3 (14.5 g, 105 mmol, 4 equiv) and iodoethane (10.5 mL, 20.5 g, 131 mmol, 5 equiv.). The reaction was heated at 6520C. overnight. After the solvent was removed, the residue was treated with H2O and extracted with EtOAc. The organic extracts were combined and washed with brine, dried over Na2SO4 and concentrated in vacuum to give the spectroscopically pure 4-(4-ethoxyphenyl)cyclohexanone (5.74 g, 100%). 1H NMR (CDCl3) 7.15 (dt, 2H), 6.86 (dt, 2H), 4.02 (q, 2H), 2.99 (tt, 1H), 2.46-2.54 (m, 4H), 2.16-2.24 (m, 2H), 1.83-2.00 (m, 2H) and 1.41 (t, 3H); MS (electrospray) m/e, 219 (M+1)+, Calcd for C14H18O2, 218.
	With potassium carbonate; In water; acetone;	Step 1 A solution of 4-(4-hydroxyphenyl)cyclohexanone (5.0 g, 26.3 mmol) in acetone (100 mL) was treated with K2CO3 (14.5 g, 105 mmol, 4 equiv) and iodoethane (10.5 mL, 20.5 g, 131 mmol, 5 equiv.). The reaction was heated at 65 C. overnight. After the solvent was removed, the residue was treated with H2O and extracted with EtOAc. The organic extracts were combined and washed with brine, dried over Na2SO4 and concentrated in vacuum to give the spectroscopically pure 4-(4-ethoxyphenyl)-cyclohexanone (5.74 g, 100%/0). 1H NMR (CDCl3) 7.15 (dt, 2H), 6.86 (dt, 2H), 4.02 (q, 2H), 2.99 (tt, 1H), 2.46-2.54 (m, 4H), 2.16-2.24 (m, 2H), 1.83-2.00 (m, 2H) and 1.41 (t, 3H); MS (electrospray) m/e, 219 (M+1)+, Calcd for C14H18O2, 218.

Reference： [1]Patent: US2001/56179,2001,A1
[2]Patent: US2002/143141,2002,A1

2
[ 105640-07-1 ]
[ 62327-21-3 ]
[ 1166827-51-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20℃;Product distribution / selectivity;	Preparation of Intermediate D:Intermediate A: tert-Butyl [4-f4-hvdroxyphenyl)cvclohexylidenel acetate To an ice-cold solution of 4-(4-hydroxy-phenyl)-cyclohexanone (15.22 g, 78.4 mmol, CAS 105640-07-1) in THF (375 mL) under N2 was added NaH in mineral oil (3.28 g, 79.3 mmol) to give a thick suspension.In a separate flask NaH in mineral oil (4.06 g, 98.0 mmol) was suspended in dry THF (375 mL) under N2. The suspension was cooled to 0 0C and tert-butyl P,P-dimethyl phosphonoacetate (16.82 mL, 82.32 mmol, CAS 62327-21-3) was added carefully. Both mixtures were stirred for ~15 min before the ice-baths were removed. After 2 h at RT the ketone solution was transferred to the ylide solution via syringe. The combined mixture was stirred under N2 overnight. The reaction was quenched by the addition of water (-100 mL) and THF was then removed under vacuum. More water was added (150 mL) and the aqueous solution was extracted with EtOAc (3chi200 mL). The combined organic layer was washed with brine (2x200 mL) and dried through a phase separator. Concentration gave product as colorless oil (24.6 g, 99 percent).1H NMR (500 MHz, CDCl3) delta 1.51 (s, 9H), 1.55-1.65 (m, 2H), 1.97-2.07 (m, 3H), 2.29- 2.40 (m, 2H), 2.70-2.78 (m, IH), 3.90-3.96 (m, IH), 4.60 (s, IH), 5.62 (s, IH), 6.77 (d, 2H), 7.09 (d, 2H). m/z 287 (M-H)".

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 10610 - 10629
[2]Patent: WO2009/81195,2009,A1 .Location in patent: Page/Page column 55

3
[ 64-67-5 ]
[ 105640-07-1 ]
[ 163671-48-5 ]

Yield	Reaction Conditions	Operation in experiment
96.5%	With potassium carbonate; In acetone; for 6.0h;Heating;	4.0% (79.0 mmol) of 4 - (4 -hydroxyphenyl) cyclohexanone,Anhydrous potassium carbonate 109.0 g (789.5 mmol),Acetone 200mL,24.4 g (157.9 mmol) of diethyl sulfate was placed in a 500 mL eggplant type flask,After heating and stirring for 6 h,Vacuum drying solvent,To the residue was added 500 mL of water,Stirred at room temperature for 2 h, filtered, washed twice,Dried to give a white solid 16.6g,Yield 96.5%,
96.5%	With potassium carbonate; In acetone; for 6.0h;Reflux;	In turn4- (4-hydroxyphenyl) cyclohexanone (15.0 g, 79.0 mmol)Anhydrous potassium carbonate 109.0 g(789.5 mmol), acetone 200 mL,24.4 g (157.9 mmol) of diethyl sulfate was placed in a 500 mL eggplant flask,Heating and refluxing for 6h, drying the solvent under reduced pressure,500 mL of water was added to the residue, stirred at room temperature for 2 h, filtered, washed twice,After drying, 16.6 g of a white solid, yield 96.5%, m.p .: 70-72 C.
96.5%	With potassium carbonate; In acetone; for 6.0h;Reflux;	15.0 g (79.0 mmol) of 4-(4-hydroxyphenyl)cyclohexanone,Anhydrous potassium carbonate 109.0 g (789.5 mmol), acetone 200 mL,24.4 g (157.9 mmol) of diethyl sulfate was placed in a 500 mL eggplant bottle, and heated under reflux for 6 hours.The solvent was evaporated to dryness under reduced pressure, and water (500 mL) was added to the residue and stirred at room temperature for 2 h.Filtering, washing twice, and drying to obtain 16.6 g of a white solid, yield 96.5%.

Reference： [1]Patent: CN105037385,2017,B .Location in patent: Paragraph 0020; 0024-0026
[2]Patent: CN105061461,2017,B .Location in patent: Paragraph 0020; 0023; 0024
[3]Patent: CN109912620,2019,A .Location in patent: Paragraph 0037; 0038; 0041-0043

4
[ 105640-07-1 ]
[ 1204-79-1 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 10893 - 10897
Angew. Chem.,2019,vol. 131,p. 11009 - 11013,5
[2]Chemical Communications,2021,vol. 57,p. 6530 - 6533

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Technical Information

? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? Grignard Reaction ? Henry Nitroaldol Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ 105640-07-1 ]

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[ 92-88-6 ]

[1,1'-Biphenyl]-4,4'-diol

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
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Code	Phrase
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P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
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P335	Brush off loose particles from skin.
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P337	If eye irritation persists:
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P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
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P353	Rinse skin with water/shower.
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P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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P370 + P378	In case of fire:
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P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
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Physical hazards
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H202	Explosive; severe projection hazard
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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
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H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
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H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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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
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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

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[ CAS No. 105640-07-1 ] {[proInfo.proName]}

Quality Control of [ 105640-07-1 ]

Related Doc. of [ 105640-07-1 ]

Product Details of [ 105640-07-1 ]

Calculated chemistry of [ 105640-07-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 105640-07-1 ]

Application In Synthesis of [ 105640-07-1 ]

[ 105640-07-1 ] Synthesis Path-Upstream 1~2

[ 105640-07-1 ] Synthesis Path-Downstream 1~4

Technical Information

Pharmaceutical Intermediates of [ 105640-07-1 ]

Artefenomel Related Intermediates

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

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