14112-98-2|7-Oxooctanoic acid| Ambeed

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Quality Control of [ 14112-98-2 ] Purity: 96% SDS Specification

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Product Details of [ 14112-98-2 ]

CAS No. :	14112-98-2
Formula :	C₈H₁₄O₃
M.W :	158.20
SMILES Code :	CC(CCCCCC(O)=O)=O
MDL No. :	MFCD00075271
InChI Key :	OSAHCBHKCKPJGI-UHFFFAOYSA-N
Pubchem ID :	26464

Safety of [ 14112-98-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P302+P352-P305+P351+P338

Computational Chemistry of [ 14112-98-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	0
Fraction Csp3	0.75
Num. rotatable bonds	6
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	42.54
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.37 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.45
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	0.63
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.61
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.	0.97
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	1.4
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.21

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.82
Solubility	23.8 mg/ml ; 0.151 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.	-1.35
Solubility	7.12 mg/ml ; 0.045 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	-1.6
Solubility	3.96 mg/ml ; 0.0251 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.	-6.82 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.	0.56

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)	1.44

Application In Synthesis of [ 14112-98-2 ]

* 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.

Downstream synthetic route of [ 14112-98-2 ]

[ 14112-98-2 ] Synthesis Path-Downstream 1~35

1
[ 758-08-7 ]
[ 14112-98-2 ]
[ 6501-93-5 ]

References: [1]Journal of the American Chemical Society,1953,vol. 75,p. 109,111.

2
[ 932-56-9 ]
[ 14112-98-2 ]

References: [1]Organic Letters,2021,vol. 23,p. 6525 - 6529.
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1929,vol. 188,p. 796.

3
[ 14112-98-2 ]
[ 64-17-5 ]
[ 36651-36-2 ]

Yield	Reaction Conditions	Operation in experiment
180 mg	With sulfuric acid; for 17h;Reflux;	(1) A mixture of <strong>[14112-98-2]7-oxooctanoic acid</strong> (158 mg), ethanol (35 mL), and concentrated sulfuric acid (500 μL) was refluxed for 17 hours. The solvent was distilled off under reduced pressure, and then, a saturated aqueous solution of sodium bicarbonate and dichloromethane were added to the residue. The organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain compound (W1) (180 mg). MS (ESI, m/z): 187.2 [M+H]+
180 mg	With sulfuric acid; for 17h;Reflux;	(1)<strong>[14112-98-2]7-oxooctanoic acid</strong> (158 mg),A mixture of ethanol (35 mL) and concentrated sulfuric acid (500 μL) was refluxed for 17 h.After distilling off the solvent under reduced pressure,Saturated aqueous sodium hydrogen carbonate solution and dichloromethane were added.The organic layer was separated, dried with anhydrous sodium sulfate,The solvent was distilled off under reduced pressure to obtain (W1) (180 mg).

References: [1]Synthesis,2007,p. 3489 - 3496.
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1936,vol. 242,p. 186.
[3]Journal of the American Chemical Society,1933,vol. 55,p. 807.
[4]Advanced Synthesis and Catalysis,2015,vol. 357,p. 4063 - 4068.
[5]Patent: US2016/199520,2016,A1 .Location in patent: Paragraph 0384; 0385.
[6]Patent: JP2016/183151,2016,A .Location in patent: Paragraph 0432-0434.

4
[ 874-23-7 ]
[ 14112-98-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iron(III) trifluoromethanesulfonate; In water; at 80℃; for 12h;	7-Oxooctanoic acid (1d) To a solution of 2-acetylcyclohexanone (1.0 g, 10 mmol) in H2O (10 mL), Fe(OTf)3 (0.25 g, 0.5 mmol) was added. The reaction mixture was vigorously stirred at 80 C for 12 h and the progress of reaction was monitored by TLC. The resulting mixture was warmed to room temperature and extracted with EtOAc (100 mL). The collected organic layer was washed with H2O (100 mL) and brine solution (100 mL).The combined organic layers were dried over MgSO4, filtered, and concentrated under reduced pressure. Purification was performed with flash chromatography on silica gel (petroleum ether: diethyl ether 6:4, Rf = 0.3) to afford keto carboxylic acid 1d as a colorless oil. Yield: 0.85 g, 85%; IR (cm-1): 3296 (O-H); 2948 (C-H); 2871 (C-H); 1702 (C=O). 1H NMR (ppm): 1.40-1.32 (m, 2H, CH2); 1.70-1.57 (m, 4H, CH2); 2.16 (s, 3H, CH3); 2.37 (t, 2H, J = 7.5 Hz, CH2); 2.46 (t, 2H, J = 7.4 Hz, CH2). 13C NMR (ppm): 23.4 (CH2); 24.5 (CH2); 28.5 (CH3); 30.0 (CH2); 33.8 (CH2); 43.5 (CH2); 177.4 (C=O); 209.0 (C=O). HRMS (ESI-) m/z calcd for C8H14O3H+ 157.0870, found 157.0874.

References: [1]European Journal of Organic Chemistry,2010,p. 2861 - 2866.
[2]Chemical Papers,2021,vol. 75,p. 3575 - 3586.
[3]Journal of the Chemical Society. Perkin transactions I,1990,p. 1423 - 1427.
[4]Journal of Medicinal Chemistry,1983,vol. 26,p. 492 - 499.
[5]Advanced Synthesis and Catalysis,2015,vol. 357,p. 4063 - 4068.
[6]Journal of the American Chemical Society,1948,vol. 70,p. 4023,4025.
[7]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1905,vol. 141,p. 1033.
Annales de Chimie (Cachan, France),1912,vol. <8> 26,p. 234.
[8]Journal of the American Chemical Society,1963,vol. 85,p. 3752 - 3753.
[9]Journal of the American Chemical Society,1988,vol. 110,p. 5203 - 5205.
[10]Tetrahedron Asymmetry,1992,vol. 3,p. 1523 - 1524.

5
[ 14112-98-2 ]
octane-1,7-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 4h;	A solution of <strong>[14112-98-2]7-oxooctanoic acid</strong> (4 g, 25.29 mmol) in THF (10 mL) was added to a stirred solution of LAH in THF (70 mL) under N2 at 0 C The mixture was allowed to warm to rt and stir at rt for 4 h, after which time 10 mL of sat. Na2SO4.10H2O (aq) was added to the solution slowly. White solid crashed out. Additional solid Na2SC>4.10H2O was added and the mixture was filtered through a plug of celite. The filtrate was diluted with EtOAc and washed with brine. The organic layer was separated, dried over Na2SC>4, filtered, and evaporated under vacuum. The residue was purified by silica gel chromatography with (0-40%) EtOAc in hexanes to obtain octane-l,7-diol (2.97 g, 20.31 mmol, 80%). XH NMR (300 MHz, CDC13) δ: ppm 3.81 (m, 1H); 3.66 (t, 2H); 1.66-1.31 (m, 12H); 1.22 (d, 3H).
80%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 4h;Inert atmosphere;	[00106] A solution of <strong>[14112-98-2]7-oxooctanoic acid</strong> (4 g, 25.29 mmol) in THF (10 mL) was added to a stirred solution of LAH in THF (70 mL) under N2 at 0 C. The mixture was allowed to warm to rt and stir at rt for 4 h, after which time 10 mL of sat. Na2S04. IOH2O (aq) was added to the solution slowly. White solid crashed out. Additional solid Na2S04. IOH2O was added and the mixture was filtered through a plug of celite. The filtrate was diluted with EtOAc and washed with brine. The organic layer was separated, dried over Na2S04, filtered, and evaporated under vacuum. The residue was purified by silica gel chromatography with (0-40%) EtOAc in hexanes to obtain octane- 1,7-diol (2.97 g, 20.31 mmol, 80%). NMR (300 MHz, CDC) δ: ppm 3.81 (m, 1H); 3.66 (t, 2H); 1.66-1.31 (m, 12H); 1.22 (d, 3H).

References: [1]European Journal of Organic Chemistry,2008,p. 4104 - 4108.
[2]Patent: WO2017/49245,2017,A2 .Location in patent: Paragraph 00480.
[3]Patent: WO2018/170306,2018,A1 .Location in patent: Paragraph 00106.
[4]Angewandte Chemie - International Edition,2019,vol. 58,p. 173 - 177.
Angew. Chem.,2019,vol. 131,p. 179 - 183,5.
[5]Journal of the American Chemical Society,1963,vol. 85,p. 3752 - 3753.

6
[ 14112-98-2 ]
[ 17173-14-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1990,p. 1423 - 1427.
[2]Journal of Organic Chemistry,2014,vol. 79,p. 11674 - 11689.
[3]Bulletin of the Chemical Society of Japan,1967,vol. 40,p. 2713 - 2714.

7
[ 1453-25-4 ]
[ 14112-98-2 ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: An ozone/oxygen mixture was bubbled througha solution of 7.34 mmol of olefin 5-8 (0.81 g of 5 [11]or 1.00 g of 6, 7, or 8 [12]) in a mixture of 50 mL ofmethylene chloride and 4 mL of acetic acid, cooled to 0(5, 6, 8) or -15C (7), until the initial compound disappeared(TLC). The mixture was purged with argon, and2 mL of 30% aqueous hydrogen peroxide and 0.2 g(1.8 mmol) of selenium dioxide were added withstirring at the same temperature as during the ozonolysis.The mixture was then stirred for at roomtemperature for 48 h and refluxed for 1 h, methylenechloride was evaporated, the residue was dissolved in50 mL of diethyl ether, and a saturated aqueous solution of NaHCO3 was added to pH 8-9. The aqueouslayer was separated, washed with diethyl ether (3×20 mL), acidified with concentrated aqueous HCl topH 4-5, and extracted with diethyl ether (3×50 mL).The combined extracts were washed over MgSO4 andevaporated.7-Oxooctanoic acid (1). Yield 0.59 g (71%),Rf 0.32 (hereinafter, petroleum ether-tert-butyl methylether, 1:1). The IR and 1H NMR spectra were identicalto those reported previously [14].

References: [1]Russian Journal of Organic Chemistry,2022,vol. 58,p. 163 - 166.
Zh. Org. Khim.,2022,vol. 58,p. 107 - 110.
[2]Bulletin de la Societe Chimique de France,1961,p. 951 - 954.
[3]Agricultural and Biological Chemistry,1981,vol. 45,p. 1029 - 1033.
[4]Canadian Journal of Chemistry,1966,vol. 44,p. 2819 - 2824.

8
[ 14112-98-2 ]
[ 138-65-8 ]
7-[2-(3,4-Dihydroxy-phenyl)-2-hydroxy-ethylamino]-octanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 492 - 499.

9
[ 14112-98-2 ]
7-Isocyanato-heptan-2-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 634 - 642.

10
[ 1453-25-4 ]
[ 14112-98-2 ]
[ 14525-83-8 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1986,vol. 35,p. 1947 - 1949.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1986,p. 2134 - 2136.

11
[ 14112-98-2 ]
[ 100-39-0 ]
[ 77128-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	Benzyl 7-oxooctanoate Benzyl 7-oxooctanoate was prepared by benzylation of <strong>[14112-98-2]7-oxooctanoic acid</strong> with benzyl bromide and potassium carbonate in dimethyl formamide.

References: [1]Tetrahedron Letters,1980,vol. 21,p. 3885 - 3888.
[2]Patent: US5248810,1993,A .

12
[ 14112-98-2 ]
[ 75-65-0 ]
[ 1003885-34-4 ]

References: [1]Synthesis,2007,p. 3489 - 3496.
[2]Tetrahedron Letters,1988,vol. 29,p. 6129 - 6132.

13
[ 67-56-1 ]
[ 14112-98-2 ]
[ 16493-42-8 ]

References: [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2527 - 2534.
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2463 - 2465.

14
[ 251922-70-0 ]
[ 14112-98-2 ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 7329 - 7332.

15
[ 14112-98-2 ]
[ 74-88-4 ]
[ 16493-42-8 ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 7329 - 7332.

16
2-acetyl-pimelic acid diethyl ester [ No CAS ]
[ 14112-98-2 ]

References: [1]Journal of the American Chemical Society,1933,vol. 55,p. 807.

17
[ 14112-98-2 ]
(E) n-Bu₃SnCH=CHCH₂CH₂OH [ No CAS ]
(E)-8-Methylene-oxacyclododec-9-en-2-one [ No CAS ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 3785 - 3786.

18
[ 14112-98-2 ]
[ 177275-01-3 ]
7-{(E)-Cyclohexyl-[4-(quinolin-2-ylmethoxy)-phenyl]-methoxyimino}-octanoic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 690 - 705.

19
[ 6066-82-6 ]
[ 14112-98-2 ]
7-oxo-octanoic acid 2,5-dioxo-pyrrolidin-1-yl ester [ No CAS ]

References: [1]Pharmazie,2001,vol. 56,p. 295 - 297.

20
[ 14112-98-2 ]
diphenyl (1-aminoethyl)phosphonate hydrobromide [ No CAS ]
diphenyl DL-1-[(7-oxooctanoyl)amino]ethylphosphonate [ No CAS ]

References: [1]Pharmazie,2001,vol. 56,p. 295 - 297.

21
[ 14112-98-2 ]
[ 100-52-7 ]
[ 13159-14-3 ]
[ 64-19-7 ]

References: [1]European Journal of Organic Chemistry,2003,p. 1631 - 1634.

22
[ 14112-98-2 ]
[ 764658-26-6 ]
5-[1-(4-butoxy-benzoyl)-5-methoxy-2-methyl-1<i>H</i>-indol-3-yl]-pentanoic acid [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 505 - 519.
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 4557 - 4562.

23
[ 14112-98-2 ]
[ 72915-12-9 ]
C₁₅H₁₆F₅NO₃ [ No CAS ]

References: [1]Analytical Chemistry,2006,vol. 78,p. 5086 - 5093.

24
[ 14112-98-2 ]
6-[1,8]naphthyridin-2-yl-hexanoic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2463 - 2465.

25
[ 14112-98-2 ]
6-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-hexanoic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2463 - 2465.

26
[ 14112-98-2 ]
6-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-hexanoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2463 - 2465.

27
[ 14112-98-2 ]
(S)-3-Quinolin-3-yl-3-(6-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl-hexanoylamino)-propionic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2463 - 2465.

28
[ 14112-98-2 ]
(S)-3-Quinolin-3-yl-3-(6-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl-hexanoylamino)-propionic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 2463 - 2465.

29
[ 14112-98-2 ]
dimethyl DL-1-[(7-oxooctanoyl)amino]ethylphosphonate [ No CAS ]

References: [1]Pharmazie,2001,vol. 56,p. 295 - 297.

30
[ 14112-98-2 ]
(E) n-Bu₃SnCH=CHCH₂CH₂OH [ No CAS ]
[ 10244-16-3 ]