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

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 1~54

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 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1175 - 1180.

23
[ 20291-40-1 ]
[ 209608-43-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1175 - 1180.

24
[ 20291-40-1 ]
6-{3-[4-Bromo-2-(3-chloro-propionylamino)-phenylsulfanyl]-phenylcarbamoyl}-hexanoic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1175 - 1180.

25
[ 20291-40-1 ]
[ 209608-46-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1175 - 1180.

26
[ 20291-40-1 ]
6-(3-{4-Bromo-2-[3-(4-methyl-piperazin-1-yl)-propionylamino]-phenylsulfanyl}-phenylcarbamoyl)-hexanoyl fluoride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1175 - 1180.

27
[ 20291-40-1 ]
[ 209608-45-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1175 - 1180.

28
[ 20291-40-1 ]
6-(4,5-Diphenyl-[2,4']bioxazolyl-5'-yl)-hexanoic acid [ No CAS ]

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

29
[ 20291-40-1 ]
[ 148114-12-9 ]

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

30
[ 20291-40-1 ]
[ 148114-10-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1993,p. 2639 - 2650.
[2]Journal of the Chemical Society. Perkin transactions I,1993,p. 2639 - 2650.
[3]Journal of the Chemical Society. Perkin transactions I,1993,p. 2999 - 3006.
[4]Journal of the Chemical Society. Chemical communications,1993,p. 410 - 412.
[5]Journal of the Chemical Society. Chemical communications,1993,p. 410 - 412.

31
[ 20291-40-1 ]
3'-N-(6-carboxy-1-oxohexyl)oxaunomycin [ No CAS ]

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

32
[ 20291-40-1 ]
methyl phenethyl pimelate [ No CAS ]

33
[ 20291-40-1 ]
[ 56188-28-4 ]

References: [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 981 - 985.

34
[ 20291-40-1 ]
[ 74509-52-7 ]

References: [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 981 - 985.

35
[ 20291-40-1 ]
3,6-Epoxytridecandisaeure-dimethylester [ No CAS ]

References: [1]Liebigs Annalen der Chemie,1985,p. 1168 - 1174.

36
[ 20291-40-1 ]
[ 78632-07-2 ]

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

37
[ 20291-40-1 ]
[ 78631-97-7 ]

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

38
[ 20291-40-1 ]
[ 78632-02-7 ]

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

39
[ 20291-40-1 ]
[ 78631-96-6 ]

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

40
[ 20291-40-1 ]
[ 78632-01-6 ]

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

41
[ 20291-40-1 ]
[ 78632-04-9 ]

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

42
[ 20291-40-1 ]
[ 78632-17-4 ]

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

43
[ 20291-40-1 ]
[ 78632-19-6 ]

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

44
[ 20291-40-1 ]
[ 78632-18-5 ]

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

45
[ 20291-40-1 ]
[ 35376-00-2 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 6769 - 6772.

46
[ 20291-40-1 ]
[ 76822-56-5 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 6769 - 6772.

47
[ 20291-40-1 ]
[ 125151-77-1 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 6769 - 6772.

48
[ 20291-40-1 ]
[ 122804-45-9 ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 6769 - 6772.

49
[ 20291-40-1 ]
7-{(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-4-methyl-oct-1-enyl]-5-oxo-cyclopentyl}-7-hydroxy-heptanoic acid methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1988,vol. 29,p. 6769 - 6772.

50
[ 67-56-1 ]
[ 111-16-0 ]
[ 1732-08-7 ]
[ 20291-40-1 ]

References: [1]Patent: US6335443,2002,B1 .Location in patent: Page column 7.

51
[ 79-37-8 ]
1-methyl-3-nitro-1-nitrosoquanidine [ No CAS ]
[ 20291-40-1 ]
[ 436152-30-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With aqueous KOH; conc. HBr; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;	Example 196A methyl 8-bromo-7-oxooctanoate A solution of <strong>[20291-40-1]7-methoxy-7-oxoheptanoic acid</strong> (4.6 g, 26.6 mmol) in dichloromethane at room temperature (200 mL) was treated with oxalyl chloride (2.55 mL) and 1 drop of DMF, stirred for 1 hour, concentrated, and dissolved in diethyl ether (2 mL) to provide solution A. A mixture of diethyl ether (150 mL) and 40% aqueous KOH (45 mL) at 0 C. was treated portionwise with 1-methyl-3-nitro-1-nitrosoquanidine (15 g), and stirred for 10 minutes. The organic phase was dried over KOH, filtered, cooled to 0 C., treated with solution A, stirred at 0 C. for 1.5 hours, treated with conc. HBr (33 mL), warmed to room temperature, and stirred for 30 minutes. The reaction was partitioned between water and ethyl acetate and the organic phase was washed with saturated NaHCO3, dried (Na2SO4), filtered and concentrated to provide 5.69 g (85% yield) of the desired product. MS (DCI) m/e 268, 270 (M+NH4)+.

References: [1]Patent: US2002/177594,2002,A1 .

52
[ 20291-40-1 ]
[ 33513-42-7 ]
[ 53367-58-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With thionyl chloride;	B. Methylpimeloyl chloride (8) Fifty three grams (53 g) of methyl hydrogen pimelate (7) (0.3 mol) from A above was mixed with thionyl chloride (30 mL, 0.4 mol) and dimethyl formamide (0.3 mL) were stirred with heating overnight (oil bath: 52 C.). The excess thionyl chloride was then removed by distillation. The crude oil which resulted was distilled (0.6 mm Hg, 80-90 C.) to provide a clear oil (54.1 g, 92%, purity≅95%. Based on NMR analysis, the clear oil was determined to be methylpimeloyl chloride (8) (1 H NMR)): 1 H NMR (300 MHz, CDCl3) δ3.67 (s, 3 H), 2.90 (t, J=7.8 Hz, 2 H), 2.33 (t, J=7.3 Hz, 2 H), 1.80-1.60 (m, 4 H), 1.45-1.30 (m, 2 H).

References: [1]Patent: US5952492,1999,A .

53
[ 20291-40-1 ]
[ 64-04-0 ]
[ 530-62-1 ]
[ 119627-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; In methanol; dichloromethane; ethyl acetate;	(j) 7-Oxo-7-[2-phenylethylamino]heptanoic acid A solution of monomethylpimelate (5.0 g) and N,N-carbonyldiimidazole (4.9 g) in dry dichloromethane (200 ml) was stirred under nitrogen at 20 for 2 hours and a solution of 2-phenylethylamine (3.22 g) in dry dichloromethane (100 ml) was then added. The mixture was stirred at 20 for 16 hours. The solution was quenched with 2N hydrochloric acid (50 ml) and separated. The organic solution was washed with water, dried (MgSO4), filtered and evaporated to leave the intermediate ester as a solid (7.05 g). A solution of the ester (7.0 g) in methanol (100 ml) and 20% sodium hydroxide solution (15 ml) was heated to reflux temperature for 3 hours. The solution was evaporated and the residue acidified with 2N hydrochloric acid. The solid mass was dissolved in ethyl acetate (400 ml), washed with water (2*100 ml), dried (MgSO4), filtered and evaporated. Crystallisation from ethyl acetate gave the sub-title acid intermediate as colourless prisms (5.7 g), mp 78-79.

References: [1]Patent: US4922022,1990,A .

54
[ 79-37-8 ]
1-hydroxy-2-naphthylhydroxylamine hydrochloride [ No CAS ]
[ 20291-40-1 ]
N-hydroxy-N-(1-hydroxy-2-naphthyl)-6-methoxycarbonylhexanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
738 mg (78%)	With triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;	EXAMPLE 3-5 Synthesis of N-hydroxy-N-(1-hydroxy-2-naphthyl)-6-methoxycarbonylhexanamide STR71 Into a 25 ml methylene chloride solution of 500 mg (2.87 mmol) of <strong>[20291-40-1]6-methoxycarbonylhexanoic acid</strong> and 222 μl (2.87 mmol) of DMF was added 564 μl (6.46 mmol) of oxalyl chloride at 0 C., and the mixture was stirred as such for one hour. The mixture was then added to a solution of 3.17 g (15 mmol) of 1-hydroxy-2-naphthylhydroxylamine hydrochloride, 3.1 ml (23 mmol) of triethylamine in THF (25 ml), and water (5 ml), at 0 C., and after stirring at 0 C. for one hour and at room temperature for one hour, the reaction was completed with aqueous KHSO4, and the mixture was extracted with methylene chloride. The organic layer was washed with 4N HCl and with saturated aqueous NaCl, and then dried over anhydrous magnesium sulfate, and after evaporation of the solvent under a reduced pressure, the residue was subjected to silica gel column chromatography to give 738 mg (78%) of the desired product. NMR (δ ppm, CDCl3) 1.2-2.0 (m, 6H), 2.25-2.6 (m, 4H), 3.7 (s, 3H), 7.05 (d, 1H, J=9 Hz), 7.2-8.0 (m, 5H), 8.4 (m, 1H), 9.7 (m, 1H)

References: [1]Patent: US5149859,1992,A .

Historical Records

Technical Information

• Acyl Group Substitution • Arndt-Eistert Homologation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Heat of Combustion • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Reactions with Organometallic Reagents • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Related Functional Groups of
[ 20291-40-1 ]

Aliphatic Chain Hydrocarbons

A128201 [34957-73-8]

Methyl 9-hydroxynonanoate

Similarity: 1.00

A128898 [1732-09-8]

Dimethyl octanedioate

Similarity: 1.00

A159778 [1501-27-5]

5-Methoxy-5-oxopentanoic acid

Similarity: 1.00

A166537 [1119-40-0]

Dimethyl glutarate

Similarity: 1.00

A277606 [627-91-8]

Monomethyl adipate

Similarity: 1.00

Esters

A128201 [34957-73-8]

Methyl 9-hydroxynonanoate

Similarity: 1.00

A128898 [1732-09-8]

Dimethyl octanedioate

Similarity: 1.00

A159778 [1501-27-5]

5-Methoxy-5-oxopentanoic acid

Similarity: 1.00

A166537 [1119-40-0]

Dimethyl glutarate

Similarity: 1.00

A277606 [627-91-8]

Monomethyl adipate

Similarity: 1.00

Carboxylic Acids

A119151 [3946-32-5]

8-Methoxy-8-oxooctanoic acid

Similarity: 1.00

A159778 [1501-27-5]

5-Methoxy-5-oxopentanoic acid

Similarity: 1.00

A202304 [3903-40-0]

12-Methoxy-12-oxododecanoic acid

Similarity: 1.00

A277606 [627-91-8]

Monomethyl adipate

Similarity: 1.00

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

{[proInfo.proName]}

CAS No.: 20291-40-1

{[proInfo.proName]}

CAS No.: 20291-40-1

Alternative Products

Product Details of [ 20291-40-1 ]

Safety of [ 20291-40-1 ]

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

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 20291-40-1 ]

[ 20291-40-1 ] Synthesis Path-Downstream 1~54

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 20291-40-1 ]

Aliphatic Chain Hydrocarbons

Esters

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

{[proInfo.proName]}

CAS No.: 20291-40-1

{[proInfo.proName]}

CAS No.: 20291-40-1

Alternative Products

Product Details of [ 20291-40-1 ]

Safety of [ 20291-40-1 ]

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

Physicochemical Properties

Lipophilicity

Water Solubility

Pharmacokinetics

Druglikeness

Medicinal Chemistry

Application In Synthesis of [ 20291-40-1 ]

[ 20291-40-1 ] Synthesis Path-Downstream 1~54

Related Products

Historical Records

Technical Information

Categories

Related Functional Groups of [ 20291-40-1 ]

Aliphatic Chain Hydrocarbons

Esters

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator

Related Functional Groups of
[ 20291-40-1 ]