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CAS No. : | 3842-86-2 | MDL No. : | MFCD30474919 |
Formula : | C8H18NO4P | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | P(=O)(OCC)(OCC)CC(=O)N(C)C |
M.W : | 223.21 g/mol | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | at 165℃; for 5.5h; | |
76% | at 110 - 115℃; Inert atmosphere; | 7 Example 7: Diethyl f2-fdimethylamino)-2-oxoethyl)phosphonate To a 500-ml 3-neck RB flask was charged triethylphosphite (284.0 g, 1674 mmol), heated to 110°C - 115°C with N2 swept through head space. 2-Chloro-N,N- dimethylacetamide was added dropwise over 3 h to 4 h at 110-115°C. The reaction mixture was aged 2 h at this temperature then concentrated under vacuum to yield desired product (313.4 g, AY=76%) as yellow oil. |
20% | at 150℃; | 8.1 8.1 Synthesis of Intermediate 21 8.1 Synthesis of Intermediate 21A mixture of 2-chloro-N,N-dimethylacetamide (300 mg, 2.47 mmol) and triethyl phosphite (820 mg, 4.94 mmol) was stirred at 150° C. overnight. The reaction mixture was cooled to room temperature and was purified by Prep HPLC to give intermediate 21 (105 mg, 20%). |
at 140 - 190℃; | ||
4.5 g | at 160℃; for 8h; Inert atmosphere; | A mixture of 2-chloro-N,N-dimethylacetamide (5.0 g, 41.1 mmol) and triethyl phosphite (6.83 g, 41.1 mmol) was degassed and purged with N2 for 3 times. The mixture was stirred at 160 °C for 8 h under N2atmosphere. The mixture was concentrated and purified by column chromatography to provide diethyl (2-(dimethylamino)-2- oxoethyl)phosphonate (I-35) (4.5 g) as a yellow oil. LCMS m/z 224.3 (M+1)+.1H NMR (400 MHz, CDCl3) ^ 4.20-4.12 (m, 4H), 3.11 (s, 3H), 3.07-3.01 (d, J = 22 Hz, 2H), 2.97 (s, 3H), 1.35-1.31 (t, J = 7.2 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium diisopropyl amide 1.) THF, hexane, 12-15 deg C, 2.) THF, hexane, RT,; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With calcium chloride for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With n-butyllithium; lithium diisopropyl amide In tetrahydrofuran; hexane at -60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With n-butyllithium In tetrahydrofuran |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 33.5% 2: 52.5% | Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 3-[(E)-3-tert-butyldimethylsilyloxy-7-phenyl-1-hepten-1-yl]cyclohexanone In tetrahydrofuran at 60℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium hydroxide In tetrahydrofuran at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: (S)-5-acetoxymethyl-3-formyl-1-(4,5-methylenedioxy-2-nitrobenzoyl)-2-pyrroline In tetrahydrofuran; hexane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With sodium hydride In diethyl ether for 0.0833333h; Stage #2: 1-vinylcyclohexanecarboxaldehyde In diethyl ether at 20℃; for 15h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With sodium hydride In tetrahydrofuran at -40 - 0℃; Stage #2: 3-formyl-1-<(4-methylphenyl)sulfonyl>pyrrole In tetrahydrofuran at 0 - 5℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With sodium hydride In benzene for 0.75h; Stage #2: pentan-3-one In benzene for 21h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 95 percent / CaCl2 / 2 h / Heating 2: 71 percent Spectr. / 3M HCl / H2O; diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 95 percent / CaCl2 / 2 h / Heating 2: 29 percent Spectr. / 3M HCl / H2O; diethyl ether / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.1% | With dimethyl sulfoxide; triethylamine | R.6.1 (E)-3-[(2S,4S)-N-Allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]-N,N-dimethylacrylamide STR371 REFERENCE EXAMPLE 6-1) (E)-3-[(2S,4S)-N-Allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]-N,N-dimethylacrylamide STR371 The same operation as in Reference Example 4-1) was carried out by using (2S,4S)-N-allyloxycarbonyl-2-hydroxymethyl-4-tritylthiopyrrolidine (the compound obtained in Reference Example 3-1); 2.00 g, 4.35 mmol), dimethyl sulfoxide (0.87 ml, 12.2 mmol), oxalyl chloride (0.56 ml, 6.5 mmol), triethylamine (3.03 ml, 21 8 mmol), 2-(diethylphosphono)-N,N-dimethylacetamide (1.17 g, 5.22 mmol) and 60% sodium hydride (174 mg, 4.35 mmol), followed by flash column chromatographic purification on silica gel (Wakogel C-300, 40 ml, elution with hexane-ethyl acetate 1 1) to give the title compound (2.02 g, 88.1% yield) NMR(CDCl3) δ: 1.6(1H,m), 2.1(1H,m), 2.7-3.4(3H,m), 2.96(3H,s), 3.0(3H,s), 4.18(1H,q,J=7 Hz), 4.46(2H,m), 5.1-5.3(2H,m), 5.82(1H,m), 6.28(1H,m), 6.6(1H,m), 7.1-7.5(15H,m) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; water | 60 EXAMPLE 60 EXAMPLE 60 This Example illustrates the synthesis of N,N-dimethyl-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenamide (compound K). To a suspension of 5 g of 55% sodium hydride in anhydrous tetrahydrofuran was added 28.5 g of N,N-dimethyldiethylphosphonoacetamide, and 16.8 g of farnesylacetone was further added and the mixture was stirred at 50° C. for 2 hours. To the liquid reaction mixture was added 100 ml of water, and the mixture was extracted with n-hexane. The extract was washed with water and dried. The solvent was removed by distillation and the residue was purified by column chromatography using silica gel to obtain 16 g of the intended compound in the form of an oil. Infrared absorption spectrum (cm-1, neat): 1650 Mass spectrum: 331 (M+) Elementary analysis values as C22 H37 ON: Calculated: C=79.70%, H=11.25%, N=4.23% Found: C=79.61%, H=11.31%, N=4.35% NMR spectrum (δ, CDCl3): 1.64 (9H, s), 1.72 (3H, s), 1.92 (3H, s) 2.0-2.2 (12H, m), 2.98 (3H, s), 3.02 (3H,s), 5.0-5.2 (3H,m), 5.8 (1H, s) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With sodium hydride In tetrahydrofuran for 0.0833333h; Stage #2: 2,2,4-trimethylpent-4-enal In tetrahydrofuran at 20℃; for 16h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With sodium hydride In tetrahydrofuran for 0.0833333h; Stage #2: 2,2,3,3-tetramethylpent-4-enal In tetrahydrofuran at 20℃; for 16h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In ethanol soln. (EtO)2POCH2CON(CH3)2 (EtOH) added to MoO2Cl2; stirring for 60 min at 25°C; liaving for 20 h at 25°C;; ppt. filtered; washed with cold EtOH/Et2O (1:4); dried for 2 h at 60°C; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol N2-atmosphere; dissoln. of NH4UCl4 in soln. of ligand, addn. of NH4PF6 soln.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol N2-atmosphere; dissoln. of NH4UCl4 in soln. of ligand, addn. of NaBPh4 soln.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium hydride In tetrahydrofuran at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
493 mg | Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1.16667h; Stage #2: 3-dimethylamino-butyraldehyde In tetrahydrofuran at 20℃; for 0.833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With sodium hydride In tetrahydrofuran at 0 - 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With sodium hydride In tetrahydrofuran at 0 - 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With sodium hydride In tetrahydrofuran at 0 - 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With sodium hydride In tetrahydrofuran at 0 - 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | Stage #1: diethyl N,N-dimethylcarbamoylmethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil Inert atmosphere; Stage #2: 4-bromo-pent-4-enal In tetrahydrofuran; mineral oil at 20℃; for 16h; Inert atmosphere; |