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Quality Control of [ 5400-79-3 ] Purity: 98% SDS Specification

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Product Details of [ 5400-79-3 ]

CAS No. :	5400-79-3
Formula :	C₈H₁₂O₃
M.W :	156.18
SMILES Code :	O=C(C1CC(CC1)=O)OCC
MDL No. :	MFCD01320352
InChI Key :	VGJWAMLZUUGEQY-UHFFFAOYSA-N
Pubchem ID :	223136

Safety of [ 5400-79-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 5400-79-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	0
Fraction Csp3	0.75
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	39.94
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	43.37 ?2

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.85
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.26
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.92
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.58
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.03

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.77
Solubility	26.3 mg/ml ; 0.168 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-0.73
Solubility	29.0 mg/ml ; 0.185 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.39
Solubility	6.32 mg/ml ; 0.0405 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-7.07 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.38

Application In Synthesis of [ 5400-79-3 ]

* 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 [ 5400-79-3 ]

[ 5400-79-3 ] Synthesis Path-Downstream 1~33

1
[ 64-17-5 ]
[ 98-78-2 ]
[ 5400-79-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With thionyl chloride; at 15 - 20℃;	General procedure: To a solution of 3-oxocyclohexane carboxylic acid (63.0g, 0.443mol) in ethanol (950mL), SOCl2 (38.8mL, 0.532mol) was added at 15C. The reaction mixture was stirred at rt overnight, and then evaporated under reduced pressure. The residue was dissolved in CHCl3 (500mL) and stirred with saturated aq NaHCO3 (200mL) for 30min. The layers were separated, and the aqueous layer was extracted with CHCl3 (2×50mL). The combined organic phases were dried over Na2SO4 and evaporated in vacuo. The residue was distilled under reduced pressure to give 23.

References: [1]Journal of Fluorine Chemistry,2017,vol. 199,p. 60 - 66.
[2]Journal of the Chemical Society,1908,vol. 93,p. 575.

2
[ 5400-79-3 ]
[ 98-78-2 ]

References: [1]Journal of the Chemical Society,1921,vol. 119,p. 499.

3
[ 5400-79-3 ]
[ 72581-31-8 ]
[ 586-45-8 ]

References: [1]Journal of Organic Chemistry,1967,vol. 32,p. 2330 - 2335.

4
[ 691-83-8 ]
[ 105-53-3 ]
[ 5400-79-3 ]

References: [1]Journal of the Chemical Society,1926,p. 1484.
[2]Journal of the Chemical Society,1926,p. 1484.
[3]Journal of the Chemical Society,1926,p. 1484.

5
[ 2409-52-1 ]
[ 105-53-3 ]
[ 5400-79-3 ]

References: [1]Journal of the Chemical Society,1926,p. 1484.
[2]Journal of the Chemical Society,1926,p. 1484.
[3]Journal of the Chemical Society,1926,p. 1484.

6
[ 83832-60-4 ]
[ 5400-79-3 ]

References: [1]Journal of the American Chemical Society,1981,vol. 103,p. 5917 - 5919.

7
[ 83844-81-9 ]
[ 5400-79-3 ]

References: [1]Journal of the American Chemical Society,1981,vol. 103,p. 5917 - 5919.

8
[ 5400-79-3 ]
6-methoxy-<2>naphthyl magnesium iodide [ No CAS ]
1-(6-methoxy-[2]naphthyl)-2-oxa-norbornan-3-one [ No CAS ]

References: [1]Journal of the Chemical Society,1941,p. 376,380.

Yield	Reaction Conditions	Operation in experiment
81%	With sulfuric acid; at 80℃; for 1h;	General procedure: A catalytic amount of concentrated sulfuric acid (10 drops) was added dropwise to a solution of 3-oxocyclopentanecarboxylic acid (5.0 g, 39.1 mmol) in methanol (50 ml). After 1 hour at 80 C, it was cooled to room temperature. The solvent was concentrated under reduced pressure and removed. To the resulting residue, a small amount of water was added. After adjusting the pH to 8 with saturated aqueous sodium bicarbonate, the mixture was extracted with ethyl acetate (30 ml × 3 times). The organic phases were combined, dried and concentrated to give the title compound (4.5 g, 81%).

11
[ 5400-79-3 ]
[ 81159-21-9 ]

References: [1]Bulletin of the Chemical Society of Japan,1957,vol. 30,p. 450,452 31<1958>333.

12
[ 691-83-8 ]
[ 5400-79-3 ]

References: [1]Journal of the Chemical Society,1926,p. 1484.

13
[ 38230-84-1 ]
[ 5400-79-3 ]

References: [1]Journal of the Chemical Society,1908,vol. 93,p. 575.

14
[ 667939-87-9 ]
[ 5400-79-3 ]
ethyl 7'-methoxy-3'-methyl-6'-(1,3-oxazol-5-yl)-4'-oxo-3',4'-dihydro-1'H-spiro[cyclopentane-1,2'-quinazoline]-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In acetic acid; at 70℃; for 2h;	Intermediate 1 (123mg), acetic acid (10ml) and ethyl [3-OXOCYCLOPENTANE-1-] carboxylate (135mg) were combined and heated to [70C] under a slight vacuum for 2 hours. After cooling to room temperature the solvent was removed in vacuo and the residue purified by column chromatography on silica to afford the title compound as an off-white solid (154mg, 81%). TLC Rf 0.525 (20% [ETOH/ETOAC).] LCMS [386] [M+H] +, RT 2.95 [MINS. 1H] NMR [300MHZ] (d6-DMSO) 8.35 (1 H, s), 7.95 [(1 H,] 2 x s), 7.35 (2H, s), 6.45 (1 H, d), 4.1 (2H, m), 3.9 (3H, 2 x s), 3.1-2. 9 (4H, m), 2.4-1. 8 (4H, m), 1.4-1. 1 (5H, m).

References: [1]Patent: WO2004/22554,2004,A1 .Location in patent: Page 56.

15
[ 5400-79-3 ]
[ 52068-30-1 ]
[ 159188-73-5 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In water; ethyl acetate;	EXAMPLE 5 1,2,3,4-Tetrahydro-7-phenylmethoxycyclopent[b]indole-2-carboxylic acid ethyl ester To 250 ml of 80% acetic acid in water, were added 4-phenylmethoxyphenylhydrazine hydrochloride (30 g, 0.12 mole) and 3-oxocyclopentane carboxylic acid ethyl ester (20 g, 0.13 mole). After stirring at ambient temperature for one hour and then at 100 C. for four hours, the mixture was cooled and poured into one liter of water. After stirring for five minutes, the mixture was extracted with ethyl acetate (3). The organic layer was washed successively with water (2) and saturated sodium chloride solution, and thereafter dried over anhydrous MgSO4. After filtering, the solution was concentrated to a dark oil (~48 g), which was eluted on a silica gel column with 5% ethyl acetate/dichloromethane via HPLC. The desired fractions were combined and concentrated to give the product as a thick brown oil (24.1 g). Analysis: Calculated for C21 H21 NO3: 75.20%C 6.31%H 4.18%N Found: 74.94%C 6.22%H 4.13%N

References: [1]Patent: US5350762,1994,A .

16
[ 98-78-2 ]
[ 75-03-6 ]
[ 5400-79-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;	A solution of cyclopentanone-3-carboxylic acid (5.00 g, 39 mmol), caesium carbonate (12.82 g, 39 mmol) and ethyl iodide (9.12 g, 4.75 ml, 58.5 mmol) in DMF (50 ml) was stirred at RT for 18 h. The mixture was then concentrated i. vac., the residue was taken up in toluene, the mixture was concentrated again and 2 N hydrochloric acid and EtOAc were then added. The aq. phase was extracted with EtOAc (3×30 ml) and the combined organic phases were washed with aq. sodium thiosulfate soln. The organic phase was dried with Na2SO4 and concentrated i. vac.Yield: 4.34 g (71%)

References: [1]Patent: US2008/306084,2008,A1 .Location in patent: Page/Page column 48.

17
[ 5400-79-3 ]
[ 1042153-25-2 ]

Yield	Reaction Conditions	Operation in experiment
61%	With diethylamino-sulfur trifluoride; In dichloromethane; for 72h;Reflux;	To a solution of DAST (45.1g, 37.0mL, 282mmol) in CH2Cl2 (450mL) a solution of 22 (11.0g, 70.4mmol) in CH2Cl2 (150mL) was added at rt. The reaction mixture was refluxed until the starting material had disappeared (ca. 72h, monitored by 1H NMR probe), then cooled, and saturated aq NaHCO3 was added to pH=7. The aqueous phase was extracted with CH2Cl2 (2×100mL), the combined organic extracts were dried over Na2SO4 and evaporated in vacuo. The residue was distilled under reduced pressure. Yield 7.71g, 61%. Colorless oil. Bp 31-32C/1.8mbar. 1H NMR (CDCl3, 400MHz): delta=4.17 (q, J=7.1Hz, 2H), 3.05-2.93 (m, 1H), 2.47-2.31 (m, 2H), 2.28-1.97 (m, 4H), 1.27 (t, J=7.1Hz, 3H). 13C NMR (CDCl3, 101MHz): delta=173.3, 131.2 (dd, J=250, 246Hz), 60.6, 40.6 (dd, J=5.4, 2.9Hz), 38.1 (t, J=26.6Hz), 34.7 (t, J=25.2Hz), 26.2 (dd, J=4.4, 3.5Hz), 13.9. 19F NMR (CDCl3, 376MHz): delta=-92.0 (dquint, J=229, 16.4Hz), -93.2 (dquint, J=229, 16.4Hz). MS (EI): m/z=178 (M+), 158 (M+-HF). Anal. Calcd for C8H12F2O2: C, 53.93; H, 6.79. Found: C, 53.89; H, 6.39.
	With diethylamino-sulfur trifluoride; In dichloromethane; at 20℃; for 50h;Inert atmosphere; Cooling with ice;	In a Teflon flask and under argon, 1.0 g of <strong>[5400-79-3]ethyl 3-oxocyclopentanecarboxylate</strong> is dissolved in 1 ml of dichloromethane. With ice cooling, 0.84 ml of diethylaminosulfur trifluoride are added. The reaction mixture is allowed to slowly warm to room temperature over a period of two hours and stirred at room temperature for another two days. The reaction mixture is then diluted by addition of 100 ml of dichloromethane, washed twice with in each case 50 ml of water, dried over MgSO4 and concentrated under reduced pressure. This gives 1.12 g of ethyl 3,3-difluoro-cyclopentanecarboxylate. C8H12F2O2 (178.20), GC-MS: 178.0 (M+).

References: [1]Journal of Fluorine Chemistry,2017,vol. 199,p. 60 - 66.
[2]Patent: US2009/325942,2009,A1 .Location in patent: Page/Page column 54.

18
[ 5400-79-3 ]
[ 107-21-1 ]
[ 6947-04-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With toluene-4-sulfonic acid; In toluene; at 80℃; for 3h;	1 L three-necked flask was charged with 100. 0 g of the compound 1,127. 6 g of ethylene glycol, 5 g of p-toluenesulfonic acid, 300 ml of toluene,Heat to 80 C for 3 h, and work up to give 112 g of pale yellow liquid. Compound 2, GC: 96.2%. Yield: 87%.
	With p-toluenesulfonic acid monohydrate; In toluene; for 4h;Reflux;	A solution of 9.9 g of <strong>[5400-79-3]ethyl 3-oxocyclopentanecarboxylate</strong>, 600 mg of p-toluenesulfonic acid monohydrate and 3.5 ml of ethylene glycol in 100 ml of toluene is heated at the boil under reflux in a water separator for four hours. The solvent is removed under reduced pressure and the residue is taken up in 250 ml of ethyl acetate and washed with 150 ml of water. The organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate as a linear gradient of n-heptane to n-heptane:ethyl acetate=7:10. This gives 8.65 g of ethyl 1,4-dioxaspiro[4.4]nonane-7-carboxylate as an oil. C10H16O4 (200.24), Rf (n-heptane:ethyl acetate=2:1)=0.38.

References: [1]Patent: CN103553872,2016,B .Location in patent: Paragraph 0065; 0068; 0069; 0070.
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3056 - 3065.
[3]Patent: US2009/325942,2009,A1 .Location in patent: Page/Page column 44; 45.

19
[ 5400-79-3 ]
[ 1187933-07-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a 0 C solution of ethyl-3-oxo-cyclopentane-l- carboxylate (2.0 g) in THF (50 mL) was added NaBH4 (970 mg). The reaction mixture was maintained at 0 C for 30 min, and then overnight at ambient temperature. The reaction was then treated with H20 and diluted with Et20. The resulting layers were separated, and the aqueous layer was further extracted with Et20. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The resulting crude product (a mixture of cis/trans isomers) was used in the next step without further purification.
	With sodium tetrahydroborate; ethanol; at 20℃;	Preparation No.39: 3-Hydroxy-cyclopentanecarboxylic acid ethyl ester; A solution of <strong>[5400-79-3]ethyl 3-oxocyclopentanecarboxylate</strong> (2.00 g, 12.81 mmol) in EtOH (20 mL) was treated with sodium borohydride (0.451 mL, 12.81 mmol) portionwise at RT (RT water bath to control exotherm) and the reaction was stirred overnight. The reaction was quenched with 2N HC1 to about pH=2 and extracted with CH2CI2, washed with water, dried over sodium sulfate, filtered and concentrated to oil. The crude product was further purified on silica gel using a gradient of 20-40% ethyl acetate in heptane. Pure product fractions and concentrate were combined to constant weight. NMR indicates an approximately 3:7 ratio of isomers. .H NMR (400 MHz, DMSO-d6) delta ppm 4.52-4.50 (m, 1H), 4.19-4.15 (m, 0.3H), 4.08-4.02 (m, 2.7H), 2.94-2.86 (m, 0.3H), 2.74-2.66 (m, 0.7H), 2.08-1.46 (m, 6H), 1.19-1.15 (m, 3H).

References: [1]Patent: WO2011/106273,2011,A1 .Location in patent: Page/Page column 71.
[2]Patent: WO2011/71570,2011,A1 .Location in patent: Page/Page column 163.

20
[ 5400-79-3 ]
[ 1332707-11-5 ]