[ CAS No. 41118-21-2 ] {[proInfo.proName]}

Name: 41118-21-2|Methyl 4-oxochroman-7-carboxylate|97%
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SKU: A297601
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2D 3D

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Quality Control of [ 41118-21-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 41118-21-2 ]

Product Details of [ 41118-21-2 ]

CAS No. :	41118-21-2	MDL No. :	MFCD14706083
Formula :	C₁₁H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VHVGLYNWKHXGJG-UHFFFAOYSA-N
M.W :	206.20	Pubchem ID :	11769654
Synonyms :

Calculated chemistry of [ 41118-21-2 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.27
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.29
TPSA :	52.6 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) :	-6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.12
Log Po/w (XLOGP3) :	1.23
Log Po/w (WLOGP) :	1.44
Log Po/w (MLOGP) :	0.9
Log Po/w (SILICOS-IT) :	2.25
Consensus Log Po/w :	1.59

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.06
Solubility :	1.81 mg/ml ; 0.00876 mol/l
Class :	Soluble
Log S (Ali) :	-1.93
Solubility :	2.41 mg/ml ; 0.0117 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.94
Solubility :	0.237 mg/ml ; 0.00115 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.21

Safety of [ 41118-21-2 ]

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 [ 41118-21-2 ]

* 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 [ 41118-21-2 ]
Downstream synthetic route of [ 41118-21-2 ]

[ 41118-21-2 ] Synthesis Path-Upstream 1~6

1
[ 67-56-1 ]
[ 201230-82-2 ]
[ 151884-08-1 ]
[ 41118-21-2 ]

Yield	Reaction Conditions	Operation in experiment
49.8%	With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 70℃; for 15 h;	Take 250mL of eggplant-shaped reaction bottle,Add magnetic stir bar,Starting material 6.2 g Compound 3,DPPP 0.86 g, Pd (OAc) 20.47 g,Methanol 13.4 g,Et3N4.23g,DMF 40 mL,CO at 70 ° C,Reaction for about 15 h.After the reaction,After the reaction solution was decompressed and the MeOH was decompressed,Add dilute aqueous HCl solution PH = 4,Add 50 mL of water to extract,And the aqueous phase was re-extracted with 50 mL of 25 mL of ethyl acetate, respectively,After the ethyl acetate phase was combined,And then extracted with saturated brine 50mL, 50mL, 25mL three times,The ethyl acetate phase was separated,Dried over anhydrous NaSO4,filter,The filtrate is dry under reduced pressure.Add 100 mL of MeOH to dissolve,Then add 3percent of the activated carbon in 70 under the conditions of reflux 1h,Filter,Spin dry,Crystallization in ether,Precipitation products 1.2g,The remaining product was separated by column chromatography to give 0.8 g of pure product,The yield was 49.8percent.

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 5, p. 1216 - 1218
[2] Patent: CN104045632, 2016, B, . Location in patent: Paragraph 0053-0055
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2071 - 2075
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 587 - 592

2
[ 67-56-1 ]
[ 90921-09-8 ]
[ 41118-21-2 ]

Yield	Reaction Conditions	Operation in experiment
83.9%	at 10 - 35℃;	To a solution of 4-oxochromane-7-carboxylic acid (500.0 mg, 2.60 mmol) and TEA (394.9, 3.90 mmol) in MeOH (10 mL) was added S0C1₂ (773.9 mg, 6.50mmol) dropwise. The mixture was stirred at room temperature overnight. Water was added, and the mixture was extracted with EtOAc . The organic layer was washed with brine, dried over Na₂SO₄, filtered and concentrated in vacuo to give the title compound (450.0 mg, yield 83.9percent) as grey solids.

Reference： [1] Patent: WO2018/30550, 2018, A1, . Location in patent: Paragraph 0573

3
[ 76240-27-2 ]
[ 41118-21-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 3, p. 587 - 592
[2] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2071 - 2075
[3] Journal of Organic Chemistry, 1994, vol. 59, # 5, p. 1216 - 1218
[4] Patent: CN104045632, 2016, B,

4
[ 151884-07-0 ]
[ 41118-21-2 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 5, p. 1216 - 1218
[2] Patent: CN104045632, 2016, B,

5
[ 42327-52-6 ]
[ 41118-21-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 8, p. 2071 - 2075

6
[ 108-46-3 ]
[ 41118-21-2 ]

Reference： [1] Patent: CN104045632, 2016, B,

[ 41118-21-2 ] Synthesis Path-Downstream 1~59

1
[ 67-56-1 ]
[ 201230-82-2 ]
[ 151884-08-1 ]
[ 41118-21-2 ]

Yield	Reaction Conditions	Operation in experiment
49.8%	With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 70℃; for 15h;	Take 250mL of eggplant-shaped reaction bottle,Add magnetic stir bar,Starting material 6.2 g Compound 3,DPPP 0.86 g, Pd (OAc) 20.47 g,Methanol 13.4 g,Et3N4.23g,DMF 40 mL,CO at 70 C,Reaction for about 15 h.After the reaction,After the reaction solution was decompressed and the MeOH was decompressed,Add dilute aqueous HCl solution PH = 4,Add 50 mL of water to extract,And the aqueous phase was re-extracted with 50 mL of 25 mL of ethyl acetate, respectively,After the ethyl acetate phase was combined,And then extracted with saturated brine 50mL, 50mL, 25mL three times,The ethyl acetate phase was separated,Dried over anhydrous NaSO4,filter,The filtrate is dry under reduced pressure.Add 100 mL of MeOH to dissolve,Then add 3% of the activated carbon in 70 under the conditions of reflux 1h,Filter,Spin dry,Crystallization in ether,Precipitation products 1.2g,The remaining product was separated by column chromatography to give 0.8 g of pure product,The yield was 49.8%.

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 1216 - 1218
[2]Patent: CN104045632,2016,B .Location in patent: Paragraph 0053-0055
[3]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2071 - 2075
[4]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 587 - 592

3
[ 41118-21-2 ]
[ 885104-11-0 ]

Yield	Reaction Conditions	Operation in experiment
86.8%	With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -10℃; for 1.5h;	Put 10 ml of 1.0M (R) -2-methyl-CBS-oxazoleborane (0.1 mmol) in a round neck flask, add toluene to dissolve, reduce to -10 C, and add 25 ml of borane dimethyl A solution of thioether (2 mmol) in toluene. At this time, 40 ml of <strong>[41118-21-2]4-oxochroman-7-carboxylic acid methyl ester</strong> (5 g, 1 mmol) diluted in tetrahydrofuran was slowly added dropwise, and the addition was completed within half an hour. , Stirred for 1 h, added 20 ml of methanol and continued stirring at 0 C for 2 h. The methanol was removed by rotary evaporation, and then extracted with 100 ml of ethyl acetate. The organic phase was washed with a 1M phosphoric acid solution, water, and a saturated saline solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. 3.9 g of an oil was obtained with a yield of 86.8% and an ee value of 98% measured by a chiral OD-H column.
		A solution of (15,2,S)-TsDPEN (1.709 g, 4.85 mmol) in isopropanol (5 niL) was added to a 35 mL schlenk-flask and cooled to 0 0C. The solution was degassed by three cycles of evacuation/nitrogen refill. Then, [RuCl2(eta-p-cymene)]2 (1.313 g, 2.425 mmol) was added, followed by TEA (1.352 mL, 9.699 mmol). The reaction mixture was heated to 80 DEG C under N2 for 1 h and cooled. The iso-propanol was removed under a stream of nitrogen, and dissolved in 10 mL acetonitrile. The catalyst solution was added to nitrogen filled 1 L 3 -N flask equipped with overhead stirring. <strong>[41118-21-2]7-Carbomethoxy-4-chromanone</strong> (100 g, 485 mmol) and 400 mL acetonitrile was added to the flask, followed by 5:2 formic acid- TEA (50 mL). The reaction mixture was incubated for 24 h at 30 DEG C. An additional portion of formic acid-TEA (5 mL) was added and the reaction mixture stirred for an additional 24 h. The solution was concentrated completely by rotary evaporation. The product was purified by crystallization from 200 mL 2-propanol and 100 mL hexanes. The solids were collected by filtration and washed with cold 2: 1 iPrOH-Hex. Final drying of the solids afforded the title compound. MS (m/z): 208.9 (m+H). Chiral HPLC showed the enantiomeric purity to be greater than 98%, when compared to racemic material,
		A solution of (15,2.S)-TSDPEN (1.709 g, 4.85 mmol) in isopropanol (5 mL) was added to a 35 mL schlenk-flask and cooled to 0 C. The solution was degassed by three cycles of evacuation/nitrogen refill. Then, [RuCl2(^6 -p-cymene)]2 (1.31 3 g, 2.425 mmol) was added, followed by TEA (1.352 mL, 9.699 mmol). The reaction mixture was heated to EPO <DP n="44"/>80 0C under N2 for 1 h and cooled. The iso-propanol was removed under a stream of nitrogen, and dissolved in 10 niL acetonitrile. The catalyst solution was added to nitrogen filled 1 L 3 -N flask equipped with overhead stirring. <strong>[41118-21-2]7-Carbomethoxy-4-chromanone</strong> (100 g, 485 mmol) and 400 mL acetonitrile was added to the flask, followed by 5:2 formic acid- 5 TEA (50 mL). The reaction mixture was incubated for 24 h at 30 0C. An additional portion of formic acid-TEA (5 mL) was added and the reaction mixture stirred for an additional 24 h. The solution was concentrated completely by rotary evaporation. The product was purified by crystallization from 200 mL 2-propanol and 100 mL hexanes. The solids were collected by filtration and washed with cold 2: 1 iPrOH-Hex. Final drying of the solids 0 afforded the title compound. MS (m/z): 208.9 (m+H). Chiral HPLC showed the enantiomeric purity to be greater than 98%, when compared to racemic material .

Reference： [1]Patent: CN110467620,2019,A .Location in patent: Paragraph 0206; 0208-0210
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2071 - 2075
[3]Patent: WO2006/44355,2006,A1 .Location in patent: Page/Page column 43
[4]Patent: WO2006/44412,2006,A1 .Location in patent: Page/Page column 41-42

4
[ 41118-21-2 ]
[ 5400-88-4 ]
[ 911376-43-7 ]
methyl 4-[(cis-4-tert-butylcyclohexyl)amino]chromane-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step B.; Methyl 4-[(trans-4-tert-butylcvclohexyl)amino]chromane-7-carboxylateA mixture of <strong>[41118-21-2]methyl 4-oxochromane-7-carboxylate</strong> (2.06 g, 9.99 mmol), titanium (IV) isopropoxide (3.27 mL, 10.99 mmol), 4-fer/-butylcyclohexyl amine (3.10 g, 19.98 mmol) in absolute ethanol (40 mL) was stirred under nitrogen at room temperature for 17 h. Sodium borohydride (0.45 g, 11.99 mmol) was then added and the resulting mixture was stirred for an additional 3 h at room temperature. The reaction was quenched by pouring into aqueous ammonia (2N, 100 mL). The resulting inorganic precipitate was filtered off through Celite and washed with CH2Cl2 (200 mL). The organic layer was separated and the remaining aqueous layer was extracted once with CH2Cl2 (100 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated. Chromatography (15% EtOAc in Hexane) afforded methyl 4-[(trans-4-tert-butylcyclohexyl)amino]chromane-7-carboxylate and the corresponding cis product (less polar). HPLC/MS: m/z = 346.3 (M+l), Rt = 1.95 min. 1H NMR (CDCl3): delta 7.57 (IH, dd, J= 2.0 Hz, 8.0 Hz), 7.50 (IH, d, J= 2.0 Hz), 7.35 (IH, d, J= 8.0 Hz), 4.36 (IH, dt, J= 2.5 Hz, 11.0 Hz), 4.27 (IH, dt, J= 4.0 Hz, 11.0 Hz), 3.97 (IH, t, J= 4.0 Hz), 3.93 (3H, s), 2.64- EPO <DP n="25"/>2.58 (IH, m), 2.18-2.15 (IH, m), 2.11-2.04 (IH, m), 1.97-1.91 (2H, m), 1.91-1.84 (2H, m), 1.22-1.02 (5H, m), 0.92 (9H, s).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 587 - 592
[2]Patent: WO2006/104826,2006,A2 .Location in patent: Page/Page column 23-24

5
[ 41118-21-2 ]
[ 41118-36-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tetrahydroborate; In methanol; at 20℃; for 0.5h;	Take 250mL of eggplant-shaped reaction bottle,Add magnetic stir bar,Ingredients 2g Compound 4,Dissolved in 30 mL of methanol,While adding NaBH 40.38 g with stirring,Closed,Reaction at room temperature,0.5h reaction is completed.After the reaction,The reaction solution was adjusted to pH = 1 with 1N HCl,Decompression of methanol,Extraction was carried out with 30 mL of ethyl acetate and water,The ethyl acetate phase was separated,Dried over anhydrous NaSO4,filter,The filtrate was chromatographed after column chromatography (ethyl acetate: n-hexane = 1: 5)A colorless transparent liquid 2g,The yield was 99%
79.2%	With methanol; sodium tetrahydroborate; In dichloromethane; at 10 - 35℃; for 1h;	To a solution of <strong>[41118-21-2]methyl 4-oxochromane-7-carboxylate</strong> (200.0 mg, 0.97 mmol) in DCM (5 mL) and MeOH (5 mL) was added NaBH4 (91.7 mg, 2.42 mmol). The mixture was stirred at room temperature for 1 h. Water was added, the mixture was and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (160.0 mg, yield 79.2%) as white solids. (3172) MS (ESI+), found 209.2 (M+H)
	With sodium borohydrid;	STARTING MATERIAL SYNTHETIC EXAMPLE 25 4-hydroxychromane-7-carboxylic Acid Methyl Ester By a similar reaction operation as in Starting Material Synthetic Example 1 using <strong>[41118-21-2]4-oxochromane-7-carboxylic acid methyl ester</strong> (1.4 g) synthesised according to a known method and sodium borohydride (0.26 g), the objective 4-hydroxychromane-7-carboxylic acid methyl ester (1.5 g) was obtained as a colorless oil. 1H-NMR(400 MHz, CDCl3) delta=1.89 (br.s, 1H), 2.0-2.2 (m, 2H), 3.90 (s, 3H), 4.25-4.35 (m, 2H), 4.8-4.9 (m, 1H), 7.35-7.45 (m, 1H), 7.51 (s, 1H), 7.5-7.6 (m, 1H)

Reference： [1]Patent: CN104045632,2016,B .Location in patent: Paragraph 0057-0059
[2]Patent: WO2018/30550,2018,A1 .Location in patent: Paragraph 0577
[3]Journal of Medicinal Chemistry,2007,vol. 50,p. 607 - 610
[4]Patent: US2003/158413,2003,A1

6
[ 76240-27-2 ]
[ 41118-21-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 587 - 592
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2071 - 2075
[3]Journal of Organic Chemistry,1994,vol. 59,p. 1216 - 1218
[4]Patent: CN104045632,2016,B

7
[ 41118-21-2 ]
[ 929010-44-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 587 - 592

8
[ 41118-21-2 ]
4-[1-(4-tert-butyl-cyclohexyl)-3-(4-trifluoromethoxy-phenyl)-ureido]-chroman-7-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 587 - 592

9
[ 41118-21-2 ]
4-[1-(4-tert-butyl-cyclohexyl)-3-(4-trifluoromethoxy-phenyl)-ureido]-chroman-7-carboxylic acid (2H-tetrazol-5-yl)-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 587 - 592

10
[ 41118-21-2 ]
3-({4-[1-(4-tert-butyl-cyclohexyl)-3-(4-trifluoromethoxy-phenyl)-ureido]-chroman-7-carbonyl}-amino)-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 587 - 592

11
[ 41118-21-2 ]
[ 784205-09-0 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 607 - 610

12
[ 41118-21-2 ]
[ 361370-00-5 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 607 - 610

13
[ 41118-21-2 ]
(S)-N-((RS)-7-formyl-2,3-dihydro-2H-chromen-4-yl)-3-(naphthalene-2-sulfonamido)-3-phenylpropanamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 607 - 610

14
[ 41118-21-2 ]
(S)-N-((RS)-7-(hydroxymethyl)-2,3-dihydro-2H-chromen-4-yl)-3-(naphthalene-2-sulfonamido)-3-phenylpropanamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 607 - 610

15
[ 41118-21-2 ]
3-(naphthalene-2-sulfonylamino)-3-phenyl-N-(7-piperidin-1-ylmethyl-chroman-4-yl)-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 607 - 610

16
[ 41118-21-2 ]
3-(naphthalene-2-sulfonylamino)-3-phenyl-N-(7-piperidin-1-ylmethyl-chroman-4-yl)-propionamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 607 - 610

17
[ 41118-21-2 ]
[ 882424-05-7 ]