20291-40-1|7-Methoxy-7-oxoheptanoic acid| Ambeed

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Quality Control of [ 20291-40-1 ] Purity: 95% SDS Specification

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Product Details of [ 20291-40-1 ]

CAS No. :	20291-40-1
Formula :	C₈H₁₄O₄
M.W :	174.19
SMILES Code :	O=C(O)CCCCCC(OC)=O
MDL No. :	MFCD00040445
InChI Key :	YOLQOHRXBGFZED-UHFFFAOYSA-N
Pubchem ID :	88467

Safety of [ 20291-40-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P272-P280-P301+P312+P330-P302+P352-P333+P313-P363-P501

Computational Chemistry of [ 20291-40-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	0
Fraction Csp3	0.75
Num. rotatable bonds	7
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	43.63
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	63.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.83
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	1.05
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.19
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.	0.93
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	1.02
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.	-1.12
Solubility	13.2 mg/ml ; 0.0759 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.	-1.98
Solubility	1.84 mg/ml ; 0.0106 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	-1.35
Solubility	7.76 mg/ml ; 0.0446 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.	-6.62 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)	1.58

Application In Synthesis of [ 20291-40-1 ]

* 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.

Downstream synthetic route of [ 20291-40-1 ]

[ 20291-40-1 ] Synthesis Path-Downstream 1~35

1
[ 111-16-0 ]
[ 1732-08-7 ]
[ 20291-40-1 ]

Yield	Reaction Conditions	Operation in experiment
68%	With hydrogenchloride; In methanol; ethyl acetate;	A. Methyl hydrogen pimelate (7) A mixture of pimelic acid (15) (75.1 g, 0.47 mol), dimethyl pimelate (50.1 g, 0.27 mol), hydrochloric acid (8 mL, 0.1 mol), methanol (25 mL, 0.62 mol) and di-n-butyl ether (20 mL) was heated (oil bath: 100-110 C.) under N2 overnight. After cooling to room temperature, EtOAc (200 mL) was added and the mixture was washed with water (2100 mL), saturated NaCl (2100 mL) and dried (Na2 SO4). The crude oil was fractionally distilled (vigreux, 125-130 C., 0.7 mm Hg) to provide a clear oil (55.5 g, 68%, purity≅95%. Based on NMR analysis, the clear oil was determined to be methyl hydrogen pimelate (7) (1 H NMR)): TLC (SiO2, MeOH/EtOAc/hexane (2:8:15, v/v)) Rf =0.25-0.34; 1 H NMR (300 MHz, CDCl3) δ3.67 (s, 3 H), 2.40-2.28 (m, 4 H), 1.72-1.58 (m, 4 H), 1.45-1.32 (m, 2 H).

References: [1]Patent: US5952492,1999,A .
[2]Chemische Berichte,1939,vol. 72,p. 455.
[3]Journal of the Chemical Society. Perkin transactions I,1980,p. 2346 - 2352.

2
[ 1732-08-7 ]
[ 20291-40-1 ]

Yield	Reaction Conditions	Operation in experiment
40%		General procedure: A solution of KOH (5.87 g, 104.65 mmol) in MeOH (150 ml) was added to dimethyl glutarate (13.15 g, 90 mmol), and the mixture was stirred for 4 h at rt. The solvent was then removed, and Et2O (100 ml) and H2O (200 ml) were added. The organic layer was separated, washed with brine, dried (MgSO4), and concentrated under reduced pressure to afford 3a as a yellow oil (4.61 g, 32%). The aqueous layer was acidified with concentrated HCl to pH 3, and extracted with Et2O (3 × 100 ml). The combined organic phase was washed with brine (3 × 100 ml) and dried (MgSO4). The solvent was removed to give a mixture of a white solid and an oil. Filtration and concentration in vacuum and purification with silica gel column chromatography gave 5.79 g (44%) of 4a as a colorless oil.
38%	With potassium hydroxide; In methanol; at 0 - 20℃; for 4h;	5.1.2 7-Methoxy-7-oxoheptanoic acid (84) A solution of KOH (5.87 g, 104.65 mmol) in CH3OH (150 ml) was added dropwise to dimethyl heptanedioate 82 (16.94 g, 90 mmol) at 0 C. The reaction mixture was allowed to be stirred for 4 h at room temperature. After removal of the solvent under reduced pressure, Et2O (100 ml) and H2O (200 ml) were added and the organic phase was concentrated to give 82 as yellow oil (5.08 g, 30%). The aqueous phase was acidified to pH 3 by concentrated HCl and extracted with Et2O (100 ml * 3). The combined organic layer was washed with brine (100 ml * 3) and dried over MgSO4. The solvent was concentrated in vacuum. Filtration and purification with silica gel column chromatography gave 5.96 g (38%) of compound 84 as colorless oil. ESI-MS m/z: 173.3 [M-H]-; 1H NMR (DMSO-d6) δ 1.23-1.31 (m, 4H), 1.44-1.57 (m, 4H), 2.19 (t, J = 7.2 Hz, 2H), 2.29 (t, J = 7.2 Hz, 2H), 3.58 (s, 3H), 11.97 (s, 1H). The synthetic procedures of compounds 85 were the same as that described above.

References: [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 1713 - 1714.
[2]Tetrahedron Letters,2020,vol. 61.
[3]Chemistry - A European Journal,2022,vol. 28.
[4]Chemische Berichte,1983,vol. 116,p. 761 - 776.
[5]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 3865 - 3872.
[6]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5766 - 5775.
[7]Journal of the Chemical Society,1935,p. 290,291.

3
[ 20291-40-1 ]
[ 35444-47-4 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; for 1h;Reflux;	General procedure: A soln of 4a (1.46 g, 10 mmol) in SOCl2 (4 ml) was refluxed for 1 h. The SOCl2 was removed under reduced pressure to afford an orange oil, which was added dropwise to a stirred solution of 2a (1.42 g, 8 mmol) and Et3N (3.5 ml, 25 mmol) in anhydrous tetrahydrofuran (65 ml) at 0 C. The reaction mixture was allowed to be stirred overnight at room temperature. The solvent was removed in vacuum and the residue was diluted with dichloromethane (150 ml), washed with 1 M H3PO4 (3 × 80 ml) and brine (3 × 80 ml) and dried over with MgSO4. Filtration and concentration in vacuum and recrystallization from AcOEt gave 1.29 g of 5a as a white crystal.
	With thionyl chloride; In benzene; for 3h;Reflux;	General procedure: A solution of monomethyl alkanoic acid (n = 3-7) (1.2 eq) and thionyl chloride (1.4 eq) in benzene (5 mL) was refluxed for 3 h. Subsequently, the majority of the SOCl2 and benzene were removed by distillation. The mixture was cooled down to room temperature and dried under a vacuum to give a crude chlorocarbonyl-alkanoic acid methyl ester. A solution of chlorocarbonyl-alkanonic acid methyl ester in dichloromethane (5 mL) was added to a round flask containing 14 (1 eq) by cannula, and subsequently added pyridine (3.5 eq). The resulting solution was stirred at room temperature overnight, and quenched by adding water. The solution was extracted with ethyl acetate, dried (MgSO4), and evaporated to give a residue which was purified by column chromatography (Al2O3), eluting by ethyl acetate /hexane (1:15) to provide 15-19.
	With thionyl chloride; for 2h;Reflux;	5.1.3 Methyl 7-((5-(4-morpholinophenyl)-1,3,4-thiadiazol-2-yl)amino)-7-oxoheptanoate (86) A soln of 84 (1.74 g, 10 mmol) in SOCl2 (4 ml) was refluxed for 2 h. The removal of SOCl2 under reduced pressure yielded orange oil, which was dissolved in dichloromethane.

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 4h;

General procedure: The oxalyl chloride (0.91 mL, 10.8 mmol) was added into thesolution of methyl 8-chloro-8-oxooctanoate (9, 680 mg, 3.6 mmol)and dry DMF (0.15 mL) in dry DCM (20 mL), then the mixturestirred at room temperature for 4 h. The excess oxalyl chloride andsolvent were evaporated under vacuum. The crude product (10) ofmonomethyl acid chloride was directly used for further reactionwithout any purification.

References: [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1175 - 1180.
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 2346 - 2352.
[3]Tetrahedron Letters,1988,vol. 29,p. 6769 - 6772.
[4]Liebigs Annalen der Chemie,1985,p. 1168 - 1174.
[5]Journal of Medicinal Chemistry,1980,vol. 23,p. 981 - 985.
[6]Patent: US6335443,2002,B1 .Location in patent: Page column 7.
[7]Tetrahedron,1977,vol. 33,p. 1105 - 1112.
[8]Chemische Berichte,1983,vol. 116,p. 761 - 776.
[9]Journal of the Chemical Society. Chemical communications,1993,p. 410 - 412.
[10]Journal of the Chemical Society. Perkin transactions I,1993,p. 2639 - 2650.
[11]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 3865 - 3872.
[12]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 5247 - 5250.
[13]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 5766 - 5775.
[14]Chemistry and Physics of Lipids,2014,vol. 184,p. 105 - 118.
[15]Chemistry - A European Journal,2017,vol. 23,p. 3107 - 3116.
[16]Tetrahedron Letters,2020,vol. 61.
[17]European Journal of Medicinal Chemistry,2020,vol. 192.
[18]Journal of the American Chemical Society,2021,vol. 143,p. 5166 - 5171.
[19]Angewandte Chemie - International Edition,2021,vol. 60,p. 23743 - 23749.
Angew. Chem.,2021,vol. 133,p. 23936 - 23942.

4
[ 108-22-5 ]
[ 20291-40-1 ]
[ 148114-06-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 2639 - 2650.
[2]Journal of the Chemical Society. Chemical communications,1993,p. 410 - 412.

5
[ 20291-40-1 ]
[ 136768-27-9 ]
[ 136768-26-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1991,p. 1981 - 1991.

6
[ 20291-40-1 ]
[ 120167-80-8 ]
[ 1731-79-9 ]
[ 120167-89-7 ]
[ 120167-84-2 ]

References: [1]Bulletin de la Societe Chimique de France,1988,p. 571 - 578.

7
[ 20291-40-1 ]
[ 120167-80-8 ]
[ 1731-79-9 ]
[ 120181-43-3 ]
[ 120167-85-3 ]

References: [1]Bulletin de la Societe Chimique de France,1988,p. 571 - 578.

8
[ 20291-40-1 ]
[ 152575-82-1 ]
6-(4,5-Diphenyl-[2,4']bioxazolyl-5'-yl)-hexanoic acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 3884 - 3903.

9
[ 20291-40-1 ]
[ 502-44-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 329 - 330.

10
[ 20291-40-1 ]
[ 1731-79-9 ]
[ 120181-43-3 ]
[ 120167-85-3 ]

References: [1]Bulletin de la Societe Chimique de France,1988,p. 571 - 578.

11
[ 20291-40-1 ]
[ 120-20-7 ]
[ 78632-03-8 ]

References: [1]Chemische Berichte,1981,vol. 114,p. 2158 - 2185.

12
[ 20291-40-1 ]
[ 75-05-8 ]
[ 83516-38-5 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 329 - 330.

13
[ 20291-40-1 ]
[ 927-80-0 ]
[ 149142-48-3 ]
C₁₆H₂₆O₇ [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 2999 - 3006.

14
[ 20291-40-1 ]
[ 174501-66-7 ]
[ 174591-15-2 ]
2,3,4,6-Tetra-O-acetyl-1,5-anhydro-1-deoxy-1-C-ethyl-α-D-glucopyranose [ No CAS ]
2,3,4,6-Tetra-O-acetyl-1,5-anhydro-1-deoxy-1-C-<7-(methoxycarbonyl)heptyl>-α-D-glucopyranose [ No CAS ]

References: [1]Liebigs Annalen,1996,p. 55 - 62.

15
[ 109-65-9 ]
[ 20291-40-1 ]
heptanedioic acid butyl ester methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 9245 - 9248.

16
[ 20291-40-1 ]
[ 100-39-0 ]
Heptanedioic acid benzyl ester methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 9245 - 9248.

17
[ 20291-40-1 ]
[ 193276-49-2 ]
methyl (+)-4-(3,10-dibromo-8-chloro-6,11-dihydro-5H-benzo[5,6]cyclo-hepta[1,2-b]pyridin-11(R)-yl)-ω-oxo-1-piperidinine-heptanoate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 139 - 143.

18
[ 20291-40-1 ]
[ 193276-77-6 ]
[ 259528-12-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 139 - 143.

19
[ 4971-56-6 ]
[ 20291-40-1 ]
[ 375374-83-7 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 998 - 1009.

20
[ 20291-40-1 ]
[ 84465-82-7 ]
[ 662151-98-6 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 998 - 1009.

21
[ 20291-40-1 ]
[ 5457-19-2 ]
[ 662151-96-4 ]

References: [1]Russian Journal of Organic Chemistry,2003,vol. 39,p. 998 - 1009.

22
[ 20291-40-1 ]
[ 209608-44-6 ]