[ CAS No. 55934-10-6 ] {[proInfo.proName]}

Name: 55934-10-6|Methyl 1-oxo-2,3-dihydro-1H-indene-4-carboxylate|95%
Brand: Ambeed
SKU: A123025
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Quality Control of [ 55934-10-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 55934-10-6 ]

Product Details of [ 55934-10-6 ]

CAS No. :	55934-10-6	MDL No. :	MFCD16037874
Formula :	C₁₁H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PGGSYJMONFCBEJ-UHFFFAOYSA-N
M.W :	190.20	Pubchem ID :	10012730
Synonyms :

Calculated chemistry of [ 55934-10-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.27
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.77
TPSA :	43.37 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) :	-6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	1.52
Log Po/w (WLOGP) :	1.6
Log Po/w (MLOGP) :	1.49
Log Po/w (SILICOS-IT) :	2.6
Consensus Log Po/w :	1.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.31 mg/ml ; 0.00689 mol/l
Class :	Soluble
Log S (Ali) :	-2.04
Solubility :	1.74 mg/ml ; 0.00914 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.19
Solubility :	0.121 mg/ml ; 0.000638 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.03

Safety of [ 55934-10-6 ]

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

Application In Synthesis of [ 55934-10-6 ]

* 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 [ 55934-10-6 ]
Downstream synthetic route of [ 55934-10-6 ]

[ 55934-10-6 ] Synthesis Path-Upstream 1~6

1
[ 67-56-1 ]
[ 201230-82-2 ]
[ 15115-60-3 ]
[ 55934-10-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	for 48 h;	Preparative Example - Methyl l-oxo-2,3-dihydro-lH-indene-4-carboxylate (PrepEx-11)PrepEx-11[00203] To a solution of 4-bromo-2,3-dihydro-lH-inden-l -one (5 g, 24 mmol) in MeOH (120 mL) and Et₃N (40 mL) was added Pd(PPh₃)₂Cl₂ (200 mg) and the mixture was stirred under 2.5 MPa of CO for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography using 2:1 petroleum ether:EtOAc to afford methyl l-oxo-2,3-dihydro-lH-indene-4-carboxylate (2.9 g, 64 percent). MS ESI calcd for CnHi₀O₃ [M + H]⁺ 191, found 191.
63%	at 100℃; for 24 h;	Into a 1000-mL pressure tank reactor was placed 4-bromo-2,3-dihydro-lH-inden-1-one (30 g, 142 mmol, 1 equiv), MeOH (450 mL), Pd(dppf)Cl₂'CH₂Cl₂ (25 g, 0.1 equiv), and Et₃N (150 mL). The resulting mixture was stirred for 24 h at 100 °C under an atmosphere of 50 MPa CO (g). After cooling to room temperature, the mixture was filtered through a pad of celite and then concentrated under vacuum. The residue was purified by normal phase chromatography on silica gel using EtO Ac/petroleum ether (1 : 10). The collected fractions were concentrated under vacuum to afford 17 g (63percent yield) of the title compound as a white solid. MS: (ES, m/z): 191 [M+H]⁺.

Reference： [1] Patent: WO2012/151137, 2012, A1, . Location in patent: Page/Page column 54
[2] Patent: WO2018/75959, 2018, A1, . Location in patent: Paragraph 0701-0702

2
[ 67-56-1 ]
[ 56461-20-2 ]
[ 55934-10-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	Reflux	Example 183: Methyl 1 -oxo-2,3-dihydro-1 H-indene-4-carboxylate A mixture of the compound of example 180 (0.700 g, 3.97 mmol), MeOH (10 mL) and 1 drop of concentrated sulfuric acid was refluxed for 12-16 h. The reaction mixture was concentrated, neutralised with saturated sodium bicarbonate solution, extracted with ethyl acetate (50 mL), dried over anhydrous Na₂SO₄, filtered, concentrated, and the residue obtained was purified by column chromatography (silica gel, 5 percent methanol in dichloromethane) to obtain the title compound. Yield: 81 percent; ¹H NMR (300 MHz, CDCI₃): δ 8.31 (d, J = 4.2 Hz, 1 H), 7.98 (d, J = 4.5 Hz, 1 H), 7.52 (t, J = 4.5 Hz, 1 H), 4.01 (s, 3H), 3.52-3.50 (m, 2H), 2.76-2.69 (m, 2H); MS (ESI+): m/z 191 (M+H)⁺

Reference： [1] Patent: WO2014/155301, 2014, A1, . Location in patent: Page/Page column 123

3
[ 4044-54-6 ]
[ 55934-10-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 19, p. 3717 - 3719

4
[ 186581-53-3 ]
[ 56461-20-2 ]
[ 55934-10-6 ]

Reference： [1] Tetrahedron Letters, 1988, vol. 29, # 34, p. 4229 - 4232

5
[ 86031-42-7 ]
[ 55934-10-6 ]

Reference： [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 19, p. 3717 - 3719

6
[ 15115-60-3 ]
[ 55934-10-6 ]

Reference： [1] Patent: WO2014/155301, 2014, A1,

[ 55934-10-6 ] Synthesis Path-Downstream 1~87

1
[ 186581-53-3 ]
[ 56461-20-2 ]
[ 55934-10-6 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 4229 - 4232

2
[ 55934-10-6 ]
[ 120493-06-3 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 4229 - 4232

3
[ 86031-42-7 ]
[ 55934-10-6 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3717 - 3719

4
[ 55934-10-6 ]
[ 143-33-9 ]
[ 168560-82-5 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3717 - 3719

5
[ 38622-91-2 ]
[ 55934-10-6 ]
[ 141-52-6 ]
[ 56461-79-1 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1978,vol. 26,p. 1776 - 1785

6
[ 69739-34-0 ]
[ 55934-10-6 ]
1-(tert-Butyl-dimethyl-silanyloxy)-3H-indene-4-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

8
(3aR,4S)-1-Oxo-2,3,3a,4-tetrahydro-1H-indene-4-carboxylic acid methyl ester [ No CAS ]
[ 55934-10-6 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 5785 - 5788

9
(1R,4R,5R,6R,9S)-9-Hydroxy-tricyclo[4.3.0.0^1,4]non-2-ene-5-carboxylic acid methyl ester [ No CAS ]
[ 55934-10-6 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 5785 - 5788

10
[ 55934-10-6 ]
(4aR,5S,8aR)-3-Methoxy-octahydro-isochromene-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

11
[ 55934-10-6 ]
(4aR,5S,8aR)-3-Isopropoxy-octahydro-isochromene-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

12
[ 55934-10-6 ]
[ 194535-27-8 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

13
[ 55934-10-6 ]
[1-(tert-Butyl-dimethyl-silanyloxy)-3H-inden-4-yl]-methanol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

14
[ 55934-10-6 ]
3-Hydroxy-1-oxo-isochroman-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

15
[ 55934-10-6 ]
3-Isopropoxy-isochroman-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

16
[ 55934-10-6 ]
5-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-isochroman-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

17
[ 55934-10-6 ]
3-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-dimethyl-silanyloxymethyl)-1H-indene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

18
[ 55934-10-6 ]
(4aR,5S,8aR)-3-(3,4-Di-tert-butyl-phenoxy)-octahydro-isochromene-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

19
[ 55934-10-6 ]
3-(3,4-Di-tert-butyl-phenoxy)-isochroman-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

20
[ 55934-10-6 ]
C₁₁H₁₈⁽²⁾H₂O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

21
[ 55934-10-6 ]
C₁₁H₁₈⁽²⁾H₂O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

22
[ 55934-10-6 ]
C₁₃H₂₂⁽²⁾H₂O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

23
[ 55934-10-6 ]
C₁₃H₂₂⁽²⁾H₂O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

24
[ 55934-10-6 ]
C₂₄H₃₆⁽²⁾H₂O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

25
[ 55934-10-6 ]
C₂₄H₃₆⁽²⁾H₂O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 8191 - 8200

26
[ 4044-54-6 ]
[ 55934-10-6 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3717 - 3719

27
[ 55934-10-6 ]
UPF 531 [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3717 - 3719

28
[ 55934-10-6 ]
[ 56461-19-9 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium tetrahydroborate; ethanol; at 0 - 20℃; for 2.5h;	Methyl 1-oxo-2,3-dihydro-1H-indene-4-carboxylate (600 mg, 3.15 mmol) was dissolved in EtOH (25m1). The reaction mixture was cooled to 0 C. Sodium borohydride (240 mg, 6.34 mmol) was added and the reaction mixture was stirred at 0 C for 30 mm. The reaction waswarmed to room temperature and stirred for 2 hours. The reaction mixture was added dropwise tosat aq NaHCO3. The quenched reaction was extracted with EtOAc (2 x 20 ml). The organics werewashed with brine, dried (MgSO4) filtered and concentrated in vacuo to yield the title compoundas an orange oil (600 mg, 84 %).1H NIVIR (500 MHz, Chloroform-d) 7.98 (d, J = 7.8 Hz, 1H), 7.63 (d, J = 7.5 Hz, 1H), 7.35 (t, J= 7.6 Hz, 1H), 5.35 - 5.22 (m, 1H), 3.93 (s, 3H), 3.56 - 3.42 (m, 1H), 3.26 - 3.08 (m, 1H), 2.62 -2.47 (m, 1H), 2.03 - 1.94 (m, 1H), 1.71 (s, 1H).LCMS Method 4 - Tr = 3.59 mm (ES+) (M+H)+ 192.2
70%		Example 184: Methyl 1 -hydroxy-2,3-dihydro-1 H-indene-4-carboxylate A mixture of the compound of example 183 (0.4 g, 2.103 mmol) and EtOH (20 mL) was stirred at 0 C for 15 min. Sodium borohydride was added to the mixture and stirred at 0 C for 30 minutes. The reaction mixture was stirred for 12-16 h at ambient temperature. The resulting mixture was concentrated, acidified with 1 M HCI solution and extracted with ethyl acetate (30 mL), dried over anhydrous Na2S04, filtered, concentrated, and the residue obtained was further used without purification. Yield: 70 %; 1H NMR (300 MHz, CDCI3): delta 7.98 (d, J = 4.5 Hz, 1 H), 7.63 (d, J = 4.2 Hz, 1 H), 7.36 (t, J = 4.5 Hz, 1 H), 5.28 (br. s, 1 H), 3.09 (s, 3H), 3.50-3.44 (m, 1 H), 3.20-3.08 (m, 1 H), 2.57-2.50 (m, 1 H), 2.06-1 .86 (m, 1 H) 1 .86 (br. s, 1 H); MS (ESI+): m/z 193 (M+H)+.
	With hydrogenchloride; sodium borohydrid; sodium chloride; In ethanol; water; acetone;	EXAMPLE 2-(1) To 120 ml. of ethanol is added 5.7 g. of <strong>[55934-10-6]methyl 1-oxo-indan-4-carboxylate</strong> and the mixture is stirred at room temperature. Then, 600 mg. of sodium borohydride is added and, after stirring for 90 minutes, 4 ml. of acetone is added. The mixture is further stirred for 30 minutes, after which the solvent is distilled off under reduced pressure. To the residue are added water and dilute hydrochloric acid, followed by extraction with ether. The extract is washed with water and a saturated aqueous solution of sodium chloride and, then, dried. Finally the solvent is distilled off under reduced pressure, whereupon methyl 1-hydroxyindan-4-carboxylate is obtained. Recrystallization from ether-petroleum ether gives crystals melting at 65-67C.

Reference： [1]Patent: WO2018/89433,2018,A1 .Location in patent: Paragraph 00326
[2]Patent: WO2014/155301,2014,A1 .Location in patent: Page/Page column 124
[3]Patent: US3953500,1976,A
[4]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6437 - 6440

29
[ 67-56-1 ]
[ 201230-82-2 ]
[ 15115-60-3 ]
[ 55934-10-6 ]

Yield	Reaction Conditions	Operation in experiment
64%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; under 18751.9 Torr; for 48h;	Preparative Example - Methyl l-oxo-2,3-dihydro-lH-indene-4-carboxylate (PrepEx-11)PrepEx-11[00203] To a solution of 4-bromo-2,3-dihydro-lH-inden-l -one (5 g, 24 mmol) in MeOH (120 mL) and Et3N (40 mL) was added Pd(PPh3)2Cl2 (200 mg) and the mixture was stirred under 2.5 MPa of CO for 48 hours. The reaction solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography using 2:1 petroleum ether:EtOAc to afford methyl l-oxo-2,3-dihydro-lH-indene-4-carboxylate (2.9 g, 64 %). MS ESI calcd for CnHi0O3 [M + H]+ 191, found 191.
63%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; triethylamine; at 100℃; under 375038.0 Torr; for 24h;	Into a 1000-mL pressure tank reactor was placed 4-bromo-2,3-dihydro-lH-inden-1-one (30 g, 142 mmol, 1 equiv), MeOH (450 mL), Pd(dppf)Cl2'CH2Cl2 (25 g, 0.1 equiv), and Et3N (150 mL). The resulting mixture was stirred for 24 h at 100 C under an atmosphere of 50 MPa CO (g). After cooling to room temperature, the mixture was filtered through a pad of celite and then concentrated under vacuum. The residue was purified by normal phase chromatography on silica gel using EtO Ac/petroleum ether (1 : 10). The collected fractions were concentrated under vacuum to afford 17 g (63% yield) of the title compound as a white solid. MS: (ES, m/z): 191 [M+H]+.

Reference： [1]Patent: WO2012/151137,2012,A1 .Location in patent: Page/Page column 54
[2]Patent: WO2018/75959,2018,A1 .Location in patent: Paragraph 0701-0702

30
4-(furan-2-yl)-2,3-dihydro-1H-inden-1-one [ No CAS ]
[ 55934-10-6 ]

Reference： [1]Patent: WO2014/155301,2014,A1

31
[ 15115-60-3 ]
[ 55934-10-6 ]

Reference： [1]Patent: WO2014/155301,2014,A1

32
[ 67-56-1 ]
[ 56461-20-2 ]
[ 55934-10-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sulfuric acid;Reflux;	Example 183: Methyl 1 -oxo-2,3-dihydro-1 H-indene-4-carboxylate A mixture of the compound of example 180 (0.700 g, 3.97 mmol), MeOH (10 mL) and 1 drop of concentrated sulfuric acid was refluxed for 12-16 h. The reaction mixture was concentrated, neutralised with saturated sodium bicarbonate solution, extracted with ethyl acetate (50 mL), dried over anhydrous Na2SO4, filtered, concentrated, and the residue obtained was purified by column chromatography (silica gel, 5 % methanol in dichloromethane) to obtain the title compound. Yield: 81 %; 1H NMR (300 MHz, CDCI3): delta 8.31 (d, J = 4.2 Hz, 1 H), 7.98 (d, J = 4.5 Hz, 1 H), 7.52 (t, J = 4.5 Hz, 1 H), 4.01 (s, 3H), 3.52-3.50 (m, 2H), 2.76-2.69 (m, 2H); MS (ESI+): m/z 191 (M+H)+

Reference： [1]Patent: WO2014/155301,2014,A1 .Location in patent: Page/Page column 123

33
[ 55934-10-6 ]
[ 56461-27-9 ]

Reference： [1]Patent: WO2014/155301,2014,A1
[2]Patent: WO2018/89433,2018,A1

34
[ 55934-10-6 ]
methyl 1-morpholino-2,3-dihydro-1H-indene-4-carboxylate [ No CAS ]

Reference： [1]Patent: WO2014/155301,2014,A1

35
[ 55934-10-6 ]
1-morpholino-2,3-dihydro-1H-indene-4-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2014/155301,2014,A1

36
[ 55934-10-6 ]
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-morpholino-2,3-dihydro-1H-indene-4-carboxamide [ No CAS ]

Reference： [1]Patent: WO2014/155301,2014,A1

37
[ 55934-10-6 ]
[ 616-38-6 ]
dimethyl 1-oxo-2,3-dihydro-1H-indene-2,4-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8 g	With sodium hydride; In mineral oil; at 80℃; for 2h;Inert atmosphere;	Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed dimethyl carbonate (180 mL) and methyl l-oxo-2,3-dihydro-1H-indene-4-carboxylate (30 g, 0.158 mol, 1 equiv). To this mixture, NaH (60% dispersion in oil, 12.6 g, 0.316 mol, 2 equiv) was added at room temperature. The resulting solution was stirred for 2 h at 80 C. The reaction was quenched by the addition of 40 mL of water and extracted with 3 x 200 mL of EtO Ac. The combined organic layers were dried over Na2S04 and concentrated under vacuum. The residue was purified by normal phase chromatography on silica gel using EtO Ac/petroleum ether (1 : 10). The collected fractions were concentrated under vacuum to afford 8 g of the title compound as a white solid. MS: (ES, m/z): 249 [M+H]+.

Reference： [1]Patent: WO2018/75959,2018,A1 .Location in patent: Paragraph 0703-0704

38
[ 55934-10-6 ]
dimethyl 2-(cyanomethyl)-1-oxo-2,3-dihydro-1H-indene-2,4-dicarboxylate [ No CAS ]