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[ CAS No. 16001-93-7 ] {[proInfo.proName]}

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Product Details of [ 16001-93-7 ]

CAS No. :16001-93-7 MDL No. :MFCD00014884
Formula : C5H14O6P2 Boiling Point : -
Linear Structure Formula :- InChI Key :XAVFZUKFLWOSOS-UHFFFAOYSA-N
M.W : 232.11 Pubchem ID :519206
Synonyms :

Safety of [ 16001-93-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16001-93-7 ]

* 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 [ 16001-93-7 ]

[ 16001-93-7 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 186581-53-3 ]
  • [ 1984-15-2 ]
  • [ 16001-93-7 ]
  • 2
  • [ 617-35-6 ]
  • [ 16001-93-7 ]
  • [ 86242-49-1 ]
  • 3
  • [ 16001-93-7 ]
  • [ 53044-26-1 ]
  • 4
  • [ 16001-93-7 ]
  • [ 17107-42-5 ]
  • 5
  • [ 1660-95-3 ]
  • [ 149-73-5 ]
  • [ 16001-93-7 ]
  • 7
  • [ 50-00-0 ]
  • [ 16001-93-7 ]
  • [ 109425-46-9 ]
YieldReaction ConditionsOperation in experiment
With diethylamine; Compound 2 was prepared as described in J. Org. Chem. 1986, 51, 3488-3490.2 was obtained as a clear liquid in 74% overall yield. 1H NMR (400 MHz, CDCl3) delta 3.78-3.81 (m, 12H), 6.94-7.12 (m, 2H).
  • 8
  • [ 141-27-5 ]
  • [ 16001-93-7 ]
  • [ 131569-48-7 ]
  • [ 115705-24-3 ]
  • 9
  • [ 141-27-5 ]
  • [ 16001-93-7 ]
  • [ 115705-24-3 ]
  • 10
  • [ 502-67-0 ]
  • [ 16001-93-7 ]
  • [ 131569-47-6 ]
  • [ 115705-17-4 ]
  • 11
  • [ 502-67-0 ]
  • [ 16001-93-7 ]
  • [ 115705-17-4 ]
  • 12
  • [ 16001-93-7 ]
  • [ 138638-39-8 ]
  • [(2R,4S)-2,4-Bis-benzyloxy-cyclohex-(E)-ylidenemethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 13
  • [ 16001-93-7 ]
  • [ 54503-64-9 ]
  • [ 90481-99-5 ]
  • [ 90482-00-1 ]
  • 14
  • [ 16001-93-7 ]
  • [ 125214-73-5 ]
  • [ 125214-74-6 ]
  • 15
  • [ 16001-93-7 ]
  • (1S,2R,4S)-2,4-Bis-benzyloxy-cyclohexanecarbaldehyde [ No CAS ]
  • [(E)-2-((1R,2R,4S)-2,4-Bis-benzyloxy-cyclohexyl)-vinyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 16
  • [ 16001-93-7 ]
  • (2R,4R,5S,6S)-4,5-Diacetoxy-6-formyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester [ No CAS ]
  • [ 118893-86-0 ]
  • 17
  • [ 16001-93-7 ]
  • [ 118892-78-7 ]
  • [ 118892-80-1 ]
  • [ 118892-79-8 ]
  • 18
  • [ 16001-93-7 ]
  • [ 45118-17-0 ]
  • [ 19929-29-4 ]
  • 21
  • [ 16001-93-7 ]
  • [ 19929-29-4 ]
  • dimethyl dichloromethanediphosphonate [ No CAS ]
  • 23
  • [ 16001-93-7 ]
  • dimethyl dichloromethanediphosphonate [ No CAS ]
  • 25
  • [ 16001-93-7 ]
  • [ 762-42-5 ]
  • [ 73574-43-3 ]
  • 26
  • [ 16001-93-7 ]
  • [ 3138-83-8 ]
  • <<3-(bromomethyl)-2-quinoxalinyl>ethenyl>phosphonic acid dimethyl ester [ No CAS ]
  • 27
  • [ 16001-93-7 ]
  • [ 19929-29-4 ]
  • tetramethyl(chloromethanediyl)bis(phosphonate) [ No CAS ]
  • 28
  • [ 16001-93-7 ]
  • [ 68363-43-9 ]
  • (E)-3-(Dimethoxy-phosphoryl)-2-[2-(trityl-amino)-thiazol-4-yl]-acrylic acid ethyl ester [ No CAS ]
  • (Z)-3-(Dimethoxy-phosphoryl)-2-[2-(trityl-amino)-thiazol-4-yl]-acrylic acid ethyl ester [ No CAS ]
  • 29
  • [ 16001-93-7 ]
  • [ 1027993-56-1 ]
  • (E)-(dimethoxy-phosphoryl)-2-<2-(trityl-amino)-thiazol-4-yl>-acrylic acid 2,3,4,5,6-pentafluoro-phenyl ester [ No CAS ]
  • [ 161722-31-2 ]
  • 30
  • [ 16001-93-7 ]
  • [ 1027993-56-1 ]
  • [ 161722-31-2 ]
  • 31
  • [ 16001-93-7 ]
  • Sodium; oxo-[2-(trityl-amino)-thiazol-4-yl]-acetate [ No CAS ]
  • Sodium; (Z)-3-(dimethoxy-phosphoryl)-2-[2-(trityl-amino)-thiazol-4-yl]-acrylate [ No CAS ]
  • 32
  • [ 16001-93-7 ]
  • 5-(t-butyldimethylsilyl)-3-(t-butyl-diphenylsilyl)-2-deoxy-D-ribose [ No CAS ]
  • [(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-ylmethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 33
  • [ 16001-93-7 ]
  • [ 183474-88-6 ]
  • [ 183475-02-7 ]
  • 34
  • [ 16001-93-7 ]
  • (2R,3R,4aS,6S,8aR)-6-Hydroxy-2,3-dimethoxy-2,3-dimethyl-8-oxo-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester [ No CAS ]
  • (2S,3S,4aR,6S,8aR)-8-[1-(Dimethoxy-phosphoryl)-meth-(E)-ylidene]-6-hydroxy-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester [ No CAS ]
  • 35
  • [ 16001-93-7 ]
  • [ 121-44-8 ]
  • [(dimethoxyphosphino)methyl]phosphonic acid monomethyl ester N,N,N-triethyl-N-methyl ammonium salt [ No CAS ]
  • 36
  • [ 16001-93-7 ]
  • [ 2215-76-1 ]
  • [(E)-2-(4-{4-[(E)-2-(Dimethoxy-phosphoryl)-vinyl]-phenoxy}-phenyl)-vinyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 37
  • [ 18997-19-8 ]
  • [ 16001-93-7 ]
  • [ 134606-34-1 ]
YieldReaction ConditionsOperation in experiment
45% With sodium iodide; In acetonitrile;Reflux; Tetramethyl methylenebisphosphonate (120 g, 0.51 mol), Nal (308 g, 2 mol), chloromethyl pivalate (387 g, 2.5 mol) and acetonitrile (400 ml) were mixed and refluxed overnight. TLC (thin-layer chromatography) in EtOAc with 5 % methanol confirmed the formation of product. The reaction mixture was diluted with ether (1000 ml) and washed with water (2 x 1000 ml), dried with Na2S03and evaporated. The solid residue was washed with cold hexane and dried in vacuum to give 148 g (45 %) of X as a pale yellow solid. NM (500 MHz, CDCI3): d 5.73-5.63 (m, 8H), 2.65 (t, 2H), 1.22 (s, 36H);31P NM (500 MHz, CDCI3): d 18.61.
  • 38
  • [ 16001-93-7 ]
  • [ 100-44-7 ]
  • [ 133918-47-5 ]
  • 40
  • [ 16001-93-7 ]
  • [ 135159-24-9 ]
  • [ 345295-12-7 ]
  • 41
  • [ 16001-93-7 ]
  • [ 4132-28-9 ]
  • [ 4291-69-4 ]
  • ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid dimethyl ester [ No CAS ]
  • 42
  • [ 16001-93-7 ]
  • [ 4132-28-9 ]
  • ((1E,3Z)-(5S,6R)-3,5,7-Tris-benzyloxy-6-hydroxy-hepta-1,3-dienyl)-phosphonic acid dimethyl ester [ No CAS ]
  • 43
  • [ 16001-93-7 ]
  • [ 357604-61-6 ]
  • [ 363619-53-8 ]
  • ((3aS,4S,5aR,9aR,9bS)-2,2,8,8-Tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-4-ylmethyl)-phosphonic acid dimethyl ester [ No CAS ]
  • 44
  • [ 16001-93-7 ]
  • 2,3-O-Isopropylidene-4,6-di-O-benzyl-D-mannopyranose [ No CAS ]
  • ((3aS,4R,6R,7R,7aS)-7-Benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl)-phosphonic acid dimethyl ester [ No CAS ]
  • [ 363619-54-9 ]
  • 45
  • [ 502-55-6 ]
  • [ 16001-93-7 ]
  • [ 545442-71-5 ]
  • 46
  • [ 16001-93-7 ]
  • methylenebis(methyl hydrogen phosphonate) [ No CAS ]
  • [ 129121-58-0 ]
  • 47
  • [ 16001-93-7 ]
  • methylenebis(methyl hydrogen phosphonate) [ No CAS ]
  • 48
  • [ 16001-93-7 ]
  • [ 1053626-17-7 ]
  • [ 753020-09-6 ]
  • 49
  • [ 2564-83-2 ]
  • [ 16001-93-7 ]
  • [ 853886-60-9 ]
  • 50
  • 3,4-di-O-benzyl-2-O-p-methoxybenzyl-L-rhamnopyranose [ No CAS ]
  • [ 16001-93-7 ]
  • [ 871116-41-5 ]
  • 51
  • [ 6138-90-5 ]
  • [ 16001-93-7 ]
  • [ 855793-00-9 ]
  • 52
  • [ 16001-93-7 ]
  • [ 117661-89-9 ]
  • [ 877760-75-3 ]
  • 53
  • [ 24280-92-0 ]
  • [ 16001-93-7 ]
  • [ 790701-36-9 ]
  • 54
  • 3-(3-phenylphenyl)benzyl bromide [ No CAS ]
  • [ 16001-93-7 ]
  • [ 950816-91-8 ]
  • 55
  • [ 16001-93-7 ]
  • [ 64382-93-0 ]
  • [2-(3,4-dibromo-phenyl)-1-(dimethoxy-phosphoryl)-ethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 56
  • [ 16001-93-7 ]
  • [ 28188-41-2 ]
  • [2-(3-cyano-phenyl)-1-(dimethoxy-phosphoryl)-ethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 57
  • [ 16001-93-7 ]
  • [ 85118-01-0 ]
  • [2-(3,4-difluoro-phenyl)-1-(dimethoxy-phosphoryl)-ethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 58
  • [ 16001-93-7 ]
  • [ 18880-04-1 ]
  • [2-(3,4-dichloro-phenyl)-1-(dimethoxy-phosphoryl)-ethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 59
  • [ 16001-93-7 ]
  • [ 64382-93-0 ]
  • (2-(3,4-dibromophenyl)ethane-1,1-diyl)bis(phosphonic acid) [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Compound 491 was prepared from 3,4-dibromobenzyl bromide (1 mmol) following general method C, followed by hydrolysis with bromotrimethylsilane as a white powder (275 mg, 65% overall yield). Anal. (C8Hi0Br2O6P2) C, H; 1H NMR (400 MHz, D2O): delta 2.78 (tt, J = 20.8 Hz, 6.8Hz, 1 H, ArCH2CH), 3.12 (td, J = 17.2Hz, 6.8Hz, 2H, ArCH2), 7.10 (d, J = 8.4Hz, 1 H, aromatic), 7.43 (d, J = 8.4Hz, 1 H, aromatic), 7.56 (s, 1 H, aromatic); 31P NMR (162 MHz, CDCI3): delta 19.87.; Tetramethyl methylenebisphosphonate (2 mmol) in dry DMF (2 ml_) was treated with NaH (2.2 mmol) in ice bath. A benzyl bromide (2 mmol) was added to the resulting solution. The reaction mixture was stirred at room temperature for 1 h before quenched with saturated NH4CI. The product was extracted with diethyl ether and purified by column chromatography.
  • 60
  • [ 945621-65-8 ]
  • [ 16001-93-7 ]
  • [ 945621-32-9 ]
  • 61
  • [ 16001-93-7 ]
  • [ 1591-95-3 ]
  • C12H14F5NO7P2 [ No CAS ]
  • 62
  • [ 16001-93-7 ]
  • [ 1795-48-8 ]
  • C9H21NO7P2 [ No CAS ]
  • 63
  • [ 16001-93-7 ]
  • [ 1609-86-5 ]
  • C10H23NO7P2 [ No CAS ]
  • 64
  • [ 16001-93-7 ]
  • [ 5416-93-3 ]
  • C13H21NO8P2 [ No CAS ]
  • 65
  • [ 16001-93-7 ]
  • [ 103-71-9 ]
  • C12H19NO7P2 [ No CAS ]
  • 66
  • [ 16001-93-7 ]
  • tetrakis-isopropoxycarbonyloxymethyl 2-(3-cyanophenyl)ethylidene-1,1-bisphosphonate [ No CAS ]
  • 67
  • [ 16001-93-7 ]
  • tetrakis-isopropoxycarbonyloxymethyl 2-(3,4-difluorophenyl)ethylidene-1,1-bisphosphonate [ No CAS ]
  • 68
  • [ 16001-93-7 ]
  • tetrakis-isopropoxycarbonyloxymethyl 2-(3,4-dichlorophenyl)ethylidene-1,1-bisphosphonate [ No CAS ]
  • 69
  • [ 16001-93-7 ]
  • tetrakis-pivaloyloxymethyl 2-(3,4-dichlorophenyl)ethylidene-1,1-bisphosphonate [ No CAS ]
  • 70
  • [ 16001-93-7 ]
  • tetrakis-pivaloyloxymethyl 2-(3,4-dibromophenyl)ethylidene-1,1-bisphosphonate [ No CAS ]
  • 71
  • [ 16001-93-7 ]
  • tetrakis-pivaloyloxymethyl 2-[3-(3-phenylphenyl)phenyl]ethylidene-1,1-bisphosphonate [ No CAS ]
  • 72
  • [ 16001-93-7 ]
  • [2-((2R,3R,4R)-3-Benzyloxy-4,5-dihydroxy-tetrahydro-furan-2-yl)-1-(dimethoxy-phosphoryl)-ethyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 73
  • [ 16001-93-7 ]
  • [(3E,7E)-1-(Dimethoxy-phosphoryl)-4,8-dimethyl-9-oxo-nona-3,7-dienyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 74
  • [ 16001-93-7 ]
  • [ 855793-01-0 ]
  • 75
  • [ 16001-93-7 ]
  • tetramethyl 4,8-dimethyl-9-phenyl-nona-3,7-dienyl-1,1-bisphosphonate [ No CAS ]
  • 76
  • [ 16001-93-7 ]
  • [ 855793-02-1 ]
  • 77
  • [ 16001-93-7 ]
  • [1-(dimethoxyphosphoryl)-3-(2,2,6,6-tetramethyl-piperidin-1-yloxy)-nonyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 78
  • [ 16001-93-7 ]
  • [4-cyano-1-(dimethoxy-phosphoryl)-3-ethoxythiocarbonylsulfanyl-butyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 79
  • [ 16001-93-7 ]
  • acetic acid 4,4-bis-(dimethoxy-phosphoryl)-2-ethoxythiocarbonylsulfanyl-butyl ester [ No CAS ]
  • 80
  • [ 16001-93-7 ]
  • [1-(dimethoxy-phosphoryl)-3-ethoxythiocarbonylsulfanyl-6-oxo-heptyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 81
  • [ 16001-93-7 ]
  • [1-(dimethoxy-phosphoryl)-3-ethoxythiocarbonylsulfanyl-4-trimethylsilanyl-butyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 82
  • [ 16001-93-7 ]
  • [4-(4-chloro-phenoxy)-1-(dimethoxy-phosphoryl)-3-ethoxythiocarbonylsulfanyl-butyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 83
  • [ 16001-93-7 ]
  • [4-[(4-bromo-phenyl)-methanesulfonyl-amino]-1-(dimethoxy-phosphoryl)-3-ethoxythiocarbonylsulfanyl-butyl]-phosphonic acid dimethyl ester [ No CAS ]
  • 84
  • [ 16001-93-7 ]
  • [ 134606-32-9 ]
  • 86
  • [ 16001-93-7 ]
  • [ 138090-80-9 ]
  • 87
  • [ 16001-93-7 ]
  • (1R,5R,6R)-5-[Bis-(dimethoxy-phosphoryl)-methoxy]-7-oxa-bicyclo[4.1.0]hept-3-ene-3-carboxylic acid methyl ester [ No CAS ]
  • 88
  • [ 16001-93-7 ]
  • 2-(Dimethoxyphosphinyl)-ethyliden-diphosphonsaeure-tetramethylester [ No CAS ]
  • 89
  • [ 675144-07-7 ]
  • [ 16001-93-7 ]
  • [ 675144-80-6 ]
YieldReaction ConditionsOperation in experiment
79% With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 15h; Example 144 To a mixture of 3-[(4-[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazole-4-carbaldehyde (0.60 g), <strong>[16001-93-7]tetramethyl methylenediphosphonate</strong> (0.32 g) and N,N-dimethylformamide (20 mL) was added sodium hydride (60% in oil, 0.05 g) at room temperature, and the mixture was stirred at the same temperature for 15 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give dimethyl (E)-2-{3-[(4-[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-methoxybenzyl)oxy]-1-phenyl-1H-pyrazol-4-yl}ethenylphosphonate as colorless crystals (0.56 g, yield 79%) from a fraction eluted with ethyl acetate-hexane (3:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 107-108C.
  • 90
  • [ 109-02-4 ]
  • [ 58844-17-0 ]
  • [ 16001-93-7 ]
  • [ 134787-45-4 ]
YieldReaction ConditionsOperation in experiment
0.72 g (16%) titanium tetrachloride; In tetrahydrofuran; EXAMPLE 7 Tetramethyl 2-(3-tert-butyl-4-hydroxy-5,6,7,8-tetrahydronaphthyl)-ethenylidene-1,1-diphosphonate Titanium tetrachloride (4.55 g, 0.024 mole) was added slowly to dry tetrahydrofuran (30 ml) which was stirred at -56. The solution was warmed to 0 and 3-tert-butyl-4-hydroxy-5,6,7,8-tetrahydro-1-naphthaldehyde (2.33 q, 0.01 mole) was added, followed by tetramethyl methylene 1,1-diphosphonate (2.78 g, 0.012 mole). N-methyl-morpholine (4.8 g, 0.048 mole) was added dropwise at 0-5. The mixture was stirred for 5 hours and then poured into ice water and extracted with diethyl ether. The ethereal extracts were washed with water until the aqueous layer attained a neutral pH and the ethereal solution was washed with aqueous saturated sodium chloride solution and dried over anhydrous sodium sulphate. The solvent was removed in vacuo to give a residue which was chromatographed on silica gel using ethyl acetate as an eluant. The chromatographed material was triturated with n-pentane: dichloromethane (10:1) to give a crystalline solid which was filtered and dried to yield 0.72 g (16%), m.p. 149-51. Microanalysis: Found C, 53.51; H, 6.98; C20 H32 O7 P2 requires C, 53.61; H, 7.23.
  • 91
  • tributyl methyl ammonium salt of trimethyl methylenebisphosphonate [ No CAS ]
  • [ 102-82-9 ]
  • [ 16001-93-7 ]
  • [ 767597-42-2 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 16 Trimethyl (monobromomethylene)bisphosphonate and its litium salt 1.04 g (2.5 moles) of the tributyl methyl ammonium salt of trimethyl methylenebisphosphonate (prepared as described in the Example 1 from tetramethyl methylenebisphosphonate and tributyl amine (31 P-NMR (CDCl3): 30.51 ppm (P), 9.54 ppm (P'), 2 JPP =6.9 Hz)) are dissolved in 40 ml of anhydrous THF and the mixture is cooled to -70 C and while stirring 4.0 ml (5.0 moles) of a 2.5 M hexane solution of BuLi is added at about -70 C. and stirring is continued for a further 10 minutes. To the mixture is added while stirring at about -60 C. 0.80 g (5.0 mmoles) of bromine in 20 ml of anhydrous THF within 10 minutes, whereafter stirring is continued for 15 minutes at about -60 C. and the mixture is heated to room temperature. The mixture is filtered and the filtrate is evaporated in a vacuum, whereby about 0.6 g (80% of theor.) of trimethyl (monobromomethylene)bisphosphonate, litium salt is obtained (31 P-NMR (CDCl3): delta 25.03 ppm (P), 11.59 (P'), 2 JPP =15.4 Hz), which by treatment with an acid may be converted to the corresponding acid.
  • 92
  • [ 16001-93-7 ]
  • [ 20057-77-6 ]
  • [ 151425-93-3 ]
YieldReaction ConditionsOperation in experiment
25% EXAMPLE 4 tetramethyl (4-methylthiophenyl)thiomethanediphosphonate STR14 3.87 g of the target compound was obtained in the form of a pale yellow oily substance by reacting 9.28 g (40 mmol) of <strong>[16001-93-7]tetramethyl methylenediphosphonate</strong> with 12.42 g (40 mmol) of bis(4-methylthiophenyl)disulfide, according to the same method as Example 1-(b). Yield: 25% 1 H-NMR (CDCl3) [ppm]: delta2.47 (s,3H), 3.36 (t,J=22 Hz,1H), 3.75-4.00 (m, 12H), 7.09-7.30 (m, 2H), 7.44-7.65 (m, 2H) IR (KBr) [cm- ]: 2960, 2858, 1576, 1479, 1446, 1392, 1259, 1185, 1106, 1029, 853 MASS (FAB) m/z: 387 (M+H)+ Elementary Analysis (as C12 H20 O6 P2 S2) Calculated values (%): C 37.31 H 5.23 Observed values (%): C 37.33 H 5.30
  • 93
  • [ 16001-93-7 ]
  • [ 109-89-7 ]
  • [ 67293-68-9 ]
YieldReaction ConditionsOperation in experiment
With paraformaldehyde; EXAMPLE II Tetramethyl ethenylidenebisphosphonate was synthesised via following general synthetic procedure. STR12 Specifically, 4.03 g (17.4 mmol) of tetramethyl methylenebisphosphonate, 2.60 g (86.7 mmol) of paraformaldehyde and 1.27 g (17.4 mmol) diethylamine were combined with the same reactants and at the same conditions as described above in Example 1 and refluxed for 2 hours. After the methanol was eliminated as described in Example I, 3.05 g of tetramethyl ethenylidenebisphosphonate was produced as a clear liquid with the following spectral characteristics: 1 H NMR (CDCl3) 6.99 (distorted dd, 2H H2 C=, J=33.9 and 37.7), (distorted dd, 12H, --OCH3, J=5.1 and 6.1); 13 C NMR (CDCl3) 150.2 (s, H2 C=), 130.2 (t, PCP, J=168), 53.2 (s, --OCH3); 31 P NMR (CDCl3) +15.5. Anal. Calcd. for C5 H14 O6 P2: C, 29.52; H, 5.78; P, 25.38. Found: C, 29.36; H, 6.01; P, 25.19.
  • 94
  • [ 941-55-9 ]
  • [ 16001-93-7 ]
  • [ 54148-00-4 ]
YieldReaction ConditionsOperation in experiment
In water; dimethyl sulfoxide; benzene; Step A Tetramethyl diazomethylenediphosphonate To potassium t-butoxide (360 mg.) in benzene (10 ml.) in an ice bath (10-15 C.) under an atmosphere of nitrogen is added <strong>[16001-93-7]tetramethyl methylene diphosphonate</strong> (696 mg.) in 2 ml. of dry dimethylsulfoxide. The solution is stirred for 15 minutes at 10-15 C., then tosyl azide (600 mg./l ml. of dimethylsulfoxide) is added. The reaction mixture is stirred at room temperature for two hours. The reaction mixture is treated with cold water. The aqueous layer is separated and extracted with methylene chloride. The organic layers are dried over magnesium sulfate, filtered and evaporated under reduced pressure to yield tetramethyl diazomethylenediphosphonate.
  • 95
  • [ 6138-90-5 ]
  • [ 16001-93-7 ]
  • [ 855793-00-9 ]
  • tetramethyl (E)-1,1-bis(4,8-dimethylnona-3,7-dienyl)-1,1-bisphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45%; 15% Synthesis of tetramethyl (E)-1,1-bis(4,8-dimethyl-nona-3,7-dienyl)-1,1-bisphosphonate (7) To a stirred suspension of NaH (0.37 g, 9.35 mmol, washed with hexanes (3×20 mL) and dried in vacuo) in THF (10 mL), 15-crown-5 (0.17 mL, 0.84 mmol) was added via syringe at 0 C. over 15 minutes. Tetramethylmethylene bisphosphonate (2.04 mL, 8.78 mmol) was added as a neat liquid to the NaH suspension over 10 minutes, and the reac0tion mixture was allowed to stir for 30 minutes. Geranyl bromide (1.8 mL, 9.45 mmol) was added dropwise as a neat liquid and the resulting solution was stirred for 2 h, and then filtered through celite and concentrated in vacuo. The resulting yellow oil was purified by flash chromatography (gradient, 0-5% methanol in Et2O) affording compound (7). 0.65 g, 15%; 1H NMR delta 5.37 (t, J=6.7 Hz, 2H), 5.11 (t, J=6.5 Hz, 2H), 3.80 (d, J=10.8 Hz, 12H), 2.62 (td, J=15.9, 7.0 Hz, 4H), 2.11-2.02 (m, 8H), 1.67 (s, 6H), 1.62 (s, 6H), 1.60 (s, 6H); 13C NMR delta 127.4 (2C), 131.1 (2C), 124.2 (2C), 118.8 (t, J=7.4 Hz, 2C), 53.1-53.0 (m, 4C), 46.3 (t, J=131.4 Hz), 39.9 (2C), 28.9 (t, J=4.4 Hz, 2C), 26.5 (2C), 25.5 (2C), 17.5 (2C), 16.1 (2C); 31P NMR +28.8 ppm. Anal. Calcd for C25H46O6P2·0.5 H2O: C, 58.47; H, 9.22. Found: C, 58.52; H, 9.18. Compound (5) Tetramethyl (E)-4,8-dimethyl-nona-3,7-dienyl-1,1-bisphosphonate was also isolated from the reaction mixture. (1.43 g, 45%): 1H NMR delta 5.27 (t, J=6.8 Hz, 1H), 5.09 (t, J=6.7 Hz, 1H), 3.83 (d, J=1.7 Hz, 6H), 3.79 (d, J=1.7 Hz, 6H), 2.64 (tt, J=17.2, 7.0 Hz, 2H), 2.38 (tt, J=24.0, 5.7 Hz, 1H), 2.16-1.16 (m, 4H), 1.68 (s, 3H), 1.65 (s, 3H), 1.60 (s, 3H); 13C NMR delta 137.1, 131.2, 123.9, 121.2 (t, J=7.2 Hz), 53.1-52.9 (m, 4C), 39.5, 36.5 (t, J=133.1 Hz), 26.4, 25.5, 23.8 (t, J=5.0 Hz), 17.5, 15.9; 31P NMR +25.7 ppm. Anal. Calcd for C15H30O6P2: C, 48.91; H, 8.21. Found: C, 48.74; H, 8.31.
  • 96
  • [ 25996-10-5 ]
  • [ 16001-93-7 ]
  • [ 1008761-11-2 ]
  • [ 1032331-69-3 ]
  • 97
  • [ 56881-57-3 ]
  • [ 16001-93-7 ]
  • [ 1008761-20-3 ]
  • C35H62O6P2 [ No CAS ]
  • 98
  • [ 24163-93-7 ]
  • [ 16001-93-7 ]
  • [ 1008761-23-6 ]
  • C35H62O6P2 [ No CAS ]
  • 99
  • [ 16001-93-7 ]
  • [ 24163-94-8 ]
  • [ 1008761-17-8 ]
  • C35H62O6P2 [ No CAS ]
  • 100
  • [ 16001-93-7 ]
  • [ 100-11-8 ]
  • [ 925684-64-6 ]
YieldReaction ConditionsOperation in experiment
30% Sodium hydride (1.02 g, 25.4 mmol) was added in portions to a stirring solution of <strong>[16001-93-7]tetramethyl methylenediphosphonate</strong> in DMF (40 mL). After 30 min a solution of 4-nitrobenzylbromide (5.00 g, 23.1 mmol) in THF (5 mL) was added and the resulting mixture was stirred at room temperature for 4.5 hr. The reaction was quenched by the addition of saturated aqueous NH4Cl (20 mL). After the addition of water (100 mL) the product was extracted with EtOAc and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated at reduced pressure. The crude product was purified by silica gel chromatography (0% to 10% MeOH in EtOAc) resulting in 58a as a colorless solid (2.55 g, 30%). 1H NMR (400 MHz, CDCl3) delta 2.65 (tt, J=6.5, 23.8, 1H), 3.31 (dt, J=6.5, 16.5, 2H), 3.73 (d, J=7.0, 6H), 3.75 (d, J=7.0, 6H), 7.42 (d, J=8.9, 2H), 8.15 (d, J=8.9, 2H).
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