67442-07-3|2-Chloro-N-methoxy-N-methylacetamide| Ambeed

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Quality Control of [ 67442-07-3 ] Purity: 98% SDS Specification

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Product Details of [ 67442-07-3 ]

CAS No. :	67442-07-3
Formula :	C₄H₈ClNO₂
M.W :	137.56
SMILES Code :	CON(C)C(=O)CCl
MDL No. :	MFCD00134232
InChI Key :	SCOJKGRNQDKFRP-UHFFFAOYSA-N
Pubchem ID :	2734716

Safety of [ 67442-07-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P280

Computational Chemistry of [ 67442-07-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	8
Num. arom. heavy atoms	0
Fraction Csp3	0.75
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	30.32
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	29.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.32
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	0.39
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.24
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.	0.42
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	-0.13
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.45

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.74
Solubility	25.0 mg/ml ; 0.182 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.	-0.58
Solubility	36.5 mg/ml ; 0.265 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	-0.67
Solubility	29.3 mg/ml ; 0.213 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	No
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.	-6.86 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	2.0
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	2.0 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)	2.0

Application In Synthesis of [ 67442-07-3 ]

* 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 [ 67442-07-3 ]

[ 67442-07-3 ] Synthesis Path-Downstream 1~35

1
[ 67442-07-3 ]
[ 133372-44-8 ]
Isopropylidene Derivative of Methyl 2-(N-Methoxy-N-methylaminocarbonylmethyl)-7,8-exo,exo-dihydroxy-6-exo-(indol-2-yl)-2-azabicyclo<2.2.2>octane-6-endo-carboxylate [ No CAS ]

References: [1]Tetrahedron,1991,vol. 47,p. 5673 - 5680.

2
[ 67442-07-3 ]
[ 133372-16-4 ]
Methyl 2-(N-Methoxy-N-methylaminocarbonylmethyl)-8,8-dimethoxy-6-exo-(indol-2-yl)-2-azabicyclo<2.2.2>octane-6-endo-carboxylate [ No CAS ]

References: [1]Tetrahedron,1991,vol. 47,p. 5673 - 5680.

3
[ 6638-79-5 ]
[ 79-04-9 ]
[ 67442-07-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; In tert-butyl methyl ether; water; at -5 - 20℃; for 3.5h;	Example 139 N-methoxy-N-methylchloroacetamide A solution of N,O-dimethylhydroxylamine hydrochloride (200 g, 2.05 mol) and tert-butyl methyl ether (2 L) was added to a cooled (0°C) solution of potassium carbonate (624 g, 4.1 mol) in water (2 L). The mixture was cooled to -5°C and chloroacetyl chloride added such that the temperature remained below 5°C. The vigorously stirred mixture was allowed to warm to room temperature and stirred for an additional 3.5 hours. The phases were separated and the aqueous phase was extracted with tert-butyl methyl ether (3 x 1 L). The combined organic phase was washed with saturated aqueous sodium chloride solution (2 x 1 L), dried (MgSO4), and concentrated. The residue was dried in vacuo to yield a white solid (257 g, 92percent). Mp 39-40.5°C; 1H NMR (CDCl3, 300 MHz) delta 4.24 (s, 2 H), 3.74 (s, 3 H), 3.22 (s, 3 H); MS (CI) 138 (MH+); Anal. calcd for C4H8ClNO2: C, 34.92; H, 5.86; N, 10.18. Found: C, 35.06; H, 5.88; N, 10.23.
92%	With potassium carbonate; In tert-butyl methyl ether; water;	EXAMPLE 139 STR92 N-methoxy-N-methylchloroacetamide A solution of N,O-dimethylhydroxylamine hydrochloride (200 g, 2.05 mol) and tert-butyl methyl ether (2 L) was added to a cooled (0° C.) solution of potassium carbonate (624 g, 4.1 mol) in water (2 L). The mixture was cooled to -5° C. and chloroacetyl chloride added such that the temperature remained below 5° C. The vigorously stirred mixture was allowed to warm to room temperature and stirred for an additional 3.5 hours. The phases were separated and the aqueous phase was extracted with tert-butyl methyl ether (31 L). The combined organic phase was washed with saturated aqueous sodium chloride solution (21 L), dried (MgSO4), and concentrated. The residue was dried in vacuo to yield a white solid (257 g, 92percent). Mp 39-40.5° C.; 1 H NMR (CDCl3, 300 MHz) delta 4.24 (s, 2 H), 3.74 (s, 3 H), 3.22 (s, 3 H); MS (CI) 138 (MH+); Anal. calcd for C4 H8 ClNO2: C, 34.92; H, 5.86; N, 10.18. Found: C, 35.06; H, 5.88; N, 10.23.
90%	With potassium carbonate; In tert-butyl methyl ether; water; at -5 - 0℃; for 2h;	A 3 L four necked flask equipped with Teflon-blade stirrer, reflux condenser and thermo-pocket was charged with N-methoxymethanamine hydrochloride (345g), water (1 .6 litre) and the resulting reaction mixture was cooled to 0 to -5 °C. Then potassium carbonate (1466 g) was added in lots to the above reaction mixture followed by the addition of methyl tert-butyl ether (1 .4 litre). The chloroacetyl chloride (400 g) was dissolved in tert-butyl methyl ether (0.2 litre) and added dropwise in to the above kept reaction mixture at - 5°C to 0°C and the reaction mixture was stirred for 2 h at 0°C. The reaction mixture was allowed to come to ambient temperature and two phases were separated. The organic layer was dried over sodium sulfate, filtered and evaporated to provide 2-chloro-N-methoxy-N-methyl-acetamide as white solid (440 g, 90percent yield and 98.0percent area purity by HPLC).

With potassium carbonate; In water; at -5 - 20℃; for 2h;

2-Chloro-N-methoxy-N-methylacetamide To a solution of potassium carbonate (93 g, 750 mmol) in H2O (300 mL) was added N,O-dimethylhydroxylamine hydrochloride (30 g, 300 mmol) at 0° C. The mixture was further cooled to -5° C., and 2-chloroacetyl chloride (40.6 g, 360 mmol) was added. The solution was stirred at room temperature for 2 h. The aqueous mixture was extracted with toluene (3*300 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to give the crude product (35 g, 85percent) as a white solid. LC/MS: m/e=138 (M+H)+.

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 1077 - 1091.
[2]European Journal of Organic Chemistry,2017,vol. 2017,p. 3917 - 3920.
[3]RSC Advances,2013,vol. 3,p. 10158 - 10162.
[4]Patent: EP1054881,2008,B1 .Location in patent: Page/Page column 57.
[5]Patent: US6051586,2000,A .
[6]Patent: WO2018/177970,2018,A1 .Location in patent: Page/Page column 70; 73.
[7]Journal of the American Chemical Society,2010,vol. 132,p. 17511 - 17515.
[8]Journal of the American Chemical Society,1990,vol. 112,p. 7001 - 7031.
[9]Tetrahedron Letters,1989,vol. 30,p. 3779 - 3780.
[10]Journal of the American Chemical Society,2008,vol. 130,p. 2916 - 2917.
[11]Journal of Molecular Structure,2010,vol. 977,p. 106 - 116.
[12]Journal of Organic Chemistry,2014,vol. 79,p. 8917 - 8925.
[13]Dalton Transactions,2015,vol. 44,p. 19464 - 19468.
[14]Patent: US2016/83391,2016,A1 .Location in patent: Paragraph 0595.
[15]Angewandte Chemie - International Edition,2017,vol. 56,p. 11594 - 11598.
Angew. Chem.,2017,vol. 129,p. 11752 - 11756,5.

4
[ 67442-07-3 ]
[ 603-35-0 ]
[ 129986-67-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	In acetonitrile; at 80℃; for 20h;	Step 1: N-Methoxy-N-methyl-2-(triphenyl-15-phosphanylidene)acetamide A mixture of (<strong>[67442-07-3]2-chloro-N-methoxy-N-methylacetamide</strong> (13.7 g, 0.1 mol) and triphenylphosphane (26.2 g, 0.1 mol) in acetonitrile (200 mL) was heated to 80° C. and held for 20 h. The mixture was cooled and concentrated to remove the solvent below 40° C. The residue was dissolved in dichloromethane (200 mL), followed by 2 N KOH (100 mL). The resulting mixture was stirred at 20° C. for 1 h. Phase separation, the organic layer was washed with brine (200 mL*3), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuum to afford N-methoxy-N-methyl-2-(triphenyl-15-phosphanylidene) acetamide (36 g, 0.1 mol, 98percent) as a yellow solid. ESI-MS (EI+, m/z): 364.4 [M+H]+.
98%	In acetonitrile; at 80℃; for 20h;	A mixture of (<strong>[67442-07-3]2-chloro-N-methoxy-N-methylacetamide</strong> (13.7 g, 0.1 mol) and triphenylphosphane (26.2 g, 0.1 mol) in acetonitrile (200 mL) was heated to 80 °C and held for 20 h. The mixture was cooled and concentrated to remove the solvent below 40 °C. The residue was dissolved in dichloromethane (200 mL), followed by 2 N KOH (100 mL). The resulting mixture was stirred at 20 °C for lh. Phase separation, the organic layer was washed with brine (200 mL*3), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuum to afford N-methoxy-N-methyl-2-(triphenyl-15-phosphanylidene) acetamide (36 g, 0.1 mol, 98percent) as a yellow solid. ESI-MS (EI, m/z): 364.4 [M+H] .
	In acetonitrile; for 18h;Heating / reflux;	Synthesis of ylide 21. To a solution of N-methoxy-N-methylhydroxylamine hydrochloride (48.52 g, 500 mmol, 1.0 equiv) in CH2Cl2 (1.0 L) at 0°C were added pyridine (80.63 mL, 1.0 mol) and chloroacetic anhydride (85.14 g, 500 mmol, 1.0 equiv). The resulting mixture was stirred for 15 min at 00C, then warm up to 23°C and stirred overnight. The reaction mixture was then poured carefully into sat. NaHCpsi3aq solution (1.0 L) and stirred 1 hour, after which the layers were separated, the aqueous phase was extracted with CHaCl2 (400 mL) and the combined organic layers were washed with IN HCl (200 mL x 2), brine (200 mL x 2), dried over Na2SO4 (10 g) and filtered. Evaporation of the solvents under reduced pressure afforded the corresponding acetamide (N-rnethoxy-N-methyl acetamide-2-chloride) as a green oil which was used in the next step without further purification. To a solution of this acetamide in CH3CN (800 mL) was added Ph3P (107.98 g, 411.7 mmol, 0.82 equiv) and the resulting mixture was refluxed for 18 hours. Then the solvents were removed under vacuum and the resulting viscous oil was dissolved in CH2Cl2 (1.0 L), washed with 2N KOH (400 mL x 2), brine (400 mL) and dried over Na2SO4 (10.0 g). Filtration and evaporation of the solvents under reduced pressure afforded ylide 21 as a thick oil which solidified by standing (146.5 g, 80percent over two steps). This compound was used in the next step without further purification. Rf = 0.85 (Hexane/EtOAc 3/1); 1H NMR (CDCl3, 400 MHz, 25 0C) 57.71-7.65 (m, 6H), 7.55-7.50 (m, 3H), 7.48-7.42 (m, 6H), 3.74 (s, 3H), 3.08 (s, 3H), 1.86 (s, IH); 13C NMR <n="150"/>(CDCl3, 100 MHz, 25 0C) 133.3 (x 3), 133,2 (x 3), 131.9 (x 3), 128.9 (x 3), 128.8 (x 3), 127.9, 61.3, 35.9.

In toluene; at 20℃; for 15h;

Dissolve N-methyl-N'-methoxy-chloroacetamide (132 g, 959 mmol) and triphenylphosphine (239 g, 911mmol) in toluene, stir at room temperature for 15 hours, and wash with 2N aqueous potassium hydroxidesolution ( 1L*2), washed with brine, dried over anhydrous sodium sulfate and evaporated

References: [1]Patent: US2017/114080,2017,A1 .Location in patent: Paragraph 0505.
[2]Patent: WO2018/200625,2018,A1 .Location in patent: Paragraph 00397; 00398; 00399; 00548; 00549; 00550.
[3]Journal of the American Chemical Society,1990,vol. 112,p. 7001 - 7031.
[4]European Journal of Organic Chemistry,2017,vol. 2017,p. 3917 - 3920.
[5]Patent: WO2008/21213,2008,A1 .Location in patent: Page/Page column 148-149.
[6]Patent: CN108658956,2018,A .Location in patent: Paragraph 0165; 0166.

5
[ 67442-07-3 ]
[ 122-52-1 ]
[ 124931-12-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	at 100℃; for 18h;	A solution of <strong>[67442-07-3]2-chloro-N-methoxy-N-methylacetamide</strong> (2.48 g,17.7 mmol) and triethyl phosphite (3.00 mL, 17.7 mmol) was heated to 100 °C for 18 h. The crude product was purified by flash column chromatography (0?2percent MeOH in CH2Cl2) to give 1 as a colorless oil; yield: 3.31 g (13.8 mmol; 78percent); Rf = 0.42 (2percent MeOH in CH2Cl2); HPLC purity (method b): >95percent (210 nm), >95percent (254 nm). IR (ATR): 2985, 2940, 2908, 1659, 1381, 1253, 1050, 1020, 998, 961 cm?1. 1H NMR (400 MHz, CDCl3): delta = 4.26?4.07 (m, 4 H, 2 × OCH2CH3), 3.76(s, 3 H, OCH3), 3.20 (s, 3 H, NCH3), 3.15 (d, J = 22.1 Hz, 2 H, 1-H), 1.33(td, J = 7.1, 0.6 Hz, 6 H, 2 × OCH2CH3). 13C NMR (101 MHz, CDCl3): delta = 166.2 (C-2), 62.7 (2 × OCH2CH3), 61.6(OCH3), 32.3 (NCH3), 30.9 (C-1), 16.5 (2 × OCH2CH3). HRMS (ESI): m/z [M + H]+ calcd for C8H19NO5P+: 240.0995; found: 240.0996.

References: [1]Tetrahedron Letters,1992,vol. 33,p. 1957 - 1958.
[2]Synthesis,2019,vol. 51,p. 757 - 768.
[3]Tetrahedron Letters,1989,vol. 30,p. 3779 - 3780.

6
[ 67442-07-3 ]
[ 4244-84-2 ]
3-[(Methoxy-methyl-carbamoyl)-methyl]-amino}-propionic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1995,vol. 36,p. 6209 - 6212.

7
[ 79-04-9 ]
[ 1117-97-1 ]
[ 67442-07-3 ]

Yield	Reaction Conditions	Operation in experiment
5.1 kg		To a solution of 21.2 kg potassium carbonate K2CO3 (153.7 mol, 3.0 eq) in 30 L H20 was added, Nu,Omicron-dimethylhydroxylamine 9 (CAS Reg. No. 1117-97-1) (5.0 kg, 51.3 mol, 1.0 eq) at 15-20 C. The reaction was stirred at rt for 30min and 30 L methyl tert-butyl ether (TBME) was added. After stirred for 30min, the mixture was cooled to 5C, and 11.6 kg of 2-Chloroacetyl chloride 8 (CAS Reg. No. 79-04-9 (102.7 mol, 2.0 eq) were added slowly. The reaction was stirred at rt overnight. Organics were separated from aqueous, and aqueous was extracted with TBME (30 L). The combined organics were washed with H20 (50 L), brine (50 L) and dried over Na2S04. Filtered and concentrated under vacuum afforded 5.1 kg of 2-chloro-N-methoxy- N-methylacetamide 10 (CAS Reg. No. 67442-07-3) as a white solid.
	With triethylamine; In dichloromethane; at 0 - 20℃;	1.2.17.1. Illustrative synthesis of Intermediate Gen-13-o : 2-Chloro-N-methoxy-N-methylacetamide [00444] To a solution of chloroacetyl chloride (0.195 mL, 1.21 mmol, 1 eq.) and TEA (0.253 mL, 1.81 mmol, 1.5 eq.) in 3 mL of DCM at 0C was added the Nu,Omicron-dimethylhydroxylamine (0.081 g, 1.33 mmol, 1.1 eq.). The reaction mixture was stirred overnight at r.t., then concentrated in vacuo. The residue was suspended in acetone and stirred vigorously for 20 min, filtered and the filtrate was concentrated in vacuo to afford Intermediate Gen-13-o which was used directly without further purification. [00445] LC-MS: MW (calcd): 137 (35C1) 139 (37C1); m/z MW (obsd): 138 (35C1 M+l), 140 (37C1 M+l)

References: [1]Tetrahedron Letters,1995,vol. 36,p. 6209 - 6212.
[2]Tetrahedron Letters,1998,vol. 39,p. 1509 - 1512.
[3]Chemical Communications,2014,vol. 50,p. 3619 - 3622.
[4]Patent: WO2014/140073,2014,A1 .Location in patent: Page/Page column 10; 25.
[5]Patent: WO2014/139882,2014,A1 .Location in patent: Paragraph 00444-00445.
[6]Angewandte Chemie - International Edition,2015,vol. 54,p. 6236 - 6240.
Angew. Chem.,2015,vol. 54,p. 6334 - 6338.
[7]Organic Process Research and Development,2019,vol. 23,p. 775 - 782.

8
[ 67442-07-3 ]
dimethyl cis-2-(2-indolyl)-4-piperidinemalonate [ No CAS ]
2-{(2S,4R)-2-(1H-Indol-2-yl)-1-[(methoxy-methyl-carbamoyl)-methyl]-piperidin-4-yl}-malonic acid dimethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 3071 - 3074.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 3158 - 3175.

9
[ 13891-87-7 ]
[ 67442-07-3 ]
[ 209806-34-8 ]