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Chemical Structure| 7598-61-0
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Product Details of [ 7598-61-0 ]

CAS No. :7598-61-0 MDL No. :MFCD00009236
Formula : C10H23O5P Boiling Point : -
Linear Structure Formula :- InChI Key :LUQYELQXRPNKRY-UHFFFAOYSA-N
M.W : 254.26 Pubchem ID :82071
Synonyms :

Calculated chemistry of [ 7598-61-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 10
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.19
TPSA : 63.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.61
Log Po/w (XLOGP3) : 0.69
Log Po/w (WLOGP) : 2.65
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 1.15
Consensus Log Po/w : 1.59

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.19
Solubility : 16.4 mg/ml ; 0.0644 mol/l
Class : Very soluble
Log S (Ali) : -1.61
Solubility : 6.28 mg/ml ; 0.0247 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.49
Solubility : 0.83 mg/ml ; 0.00327 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.21

Safety of [ 7598-61-0 ]

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

Application In Synthesis of [ 7598-61-0 ]

* 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 [ 7598-61-0 ]

[ 7598-61-0 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 7598-61-0 ]
  • (2,2-diethoxy-1-bromo-ethyl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; bromine; calcium carbonate
  • 2
  • [ 7598-61-0 ]
  • [ 1606-75-3 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride In water Inert atmosphere; General procedure for acetal deprotection. General procedure: A solution of the acetal in an aqueous 2M HCl (3 mL/mmole) solution was stirred at room temperature under argon overnight. The reaction mixture was extracted several times with CHCl3. The combined organic layers were dried on anhydrous Na2SO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography. 2-Oxoethylphosphonic acid diethyl ester (18a) (colorless oil, 2.12 g, 11.8 mmol, 99%, RF = 0.26, EtOAc). 1H-NMR (300 MHz, CDCl3): δ (ppm) = 1.26 (6H, t, J = 7.5 Hz, CH3), 3.00 (2H, dd, J = 3.3 Hz, 21 Hz, P-CH2), 4.03-4.14 (4H, m, CH2- CH3), 9.58 (1H, td, J = 0.9 Hz, 3.3 Hz, CHO). 13C-NMR (75.5 MHz, CDCl3): δ (ppm) = 16.3 (d, J = 6.1 Hz), 43.2 (d, J = 127 Hz), 62.7 (d, J = 6.7 Hz), 193.0 (d, J = 6.1 Hz). 31P-NMR (121.5 MHz, CDCl3): δ (ppm) = 20.1. HRMS (EI+) calculated m/z for C6H 13O4PNa [M+Na]+ 203.044, found 203.042.
95% With amberlyst-15 In water; acetone for 18h;
90% With Amberlist-15 In water; acetone at 20℃; for 24h; 1 EXAMPLE 1; Preparation of the compound of formula (III) wherein R9 is Et; 10 mmol of diethylphosphonoacetaldehyde diethyl acetal (compound of formula (II) wherein R2 is Et) and 0.4 g of Amberlist@-15 were added to a solution of 40 ml of acetone containing 0.6 ml of water. The mixture was left under stirring for 24 hours at room temperature, filtered and then evaporated at reduced pressure. The residue purified by flash chromatography using a chloroform methanol mixture 98: 2 as eluent provided the pure aldehyde of formula (III) wherein R2 is Et (yield = 90%).
81% With acid
80% With hydrogenchloride at 90 - 92℃; for 1.5h;
80% With hydrogenchloride In water for 2h; Reflux;
70% With hydrogenchloride for 0.166667h; Heating;
66% With Dowex-50W H+ form In water
55% With hydrogenchloride In water at 20℃; for 20h; Diethyl (2-oxoethyl)-phosphonate: iii Diethyl 2,2-diethoxyethylphosphonate (1.27 g, 5.00 mmol) was dissolved in HCl (2 M, 15 mL) and the reaction mixture was stirred at room temperature for 20 h. The aqueous mixture was extracted with EtOAc(4 x 10 mL), dried (Na2SO4) and the solvent was removed in vacuo. The crude aldehyde could be purified by bulb-to-bulb distillation ( 0.37 mbar/ 65-90°C) to obtain a colourless liquid (495 mg, 2.80 mmol, 55%). The product was stored at -25°C. 1H NMR (CDCl3, 400.27 MHz): δ = 9.64 (td, J = 3.2 Hz, 0.9 Hz, 1H, CHO), 4.22-4.09 (m, 4H, -OCH2), 3.05 (dd, J= 21.9 Hz, 3.2 Hz, 2H, P-CH2), 1.32 (td, J = 7.1 Hz, 0.2 Hz, 6H, CH3). 31P NMR (CDCl3, 162.04 MHz): δ = 18.90 (s, product, 94 mol%), 33.65 (s, P(OEt)3, 6 mol%).
55% With hydrogenchloride In water at 20℃; for 20h;
With hydrogenchloride
With ion-exchange resin + form>
With hydrogenchloride; hydroquinone
With hydrogenchloride
With hydrogenchloride for 0.75h; Heating;
With Amberlist-15 In acetone at 20℃;
33.91 g With 2percent aq. HCl Heating;
With hydrogenchloride In water at 20℃; for 8h;
With water; toluene-4-sulfonic acid In acetone at 20℃; for 96h; Inert atmosphere;
With toluene-4-sulfonic acid In water; acetone at 25℃; for 96h; Inert atmosphere;
With hydrogenchloride In water at 50℃; for 4h; Inert atmosphere; I Diethyl formylmethylphosphonate (Step I) Diethyl formylmethylphosphonate (Step I) A 2-litre, four-necked flask equipped with a mechanical stirrer, an addition funnel and a nitrogen inlet was charged with diethyl 2,2-diethoxyethylphosphonate (150 g) and water (300 mL), and a slight stream of nitrogen was continuously passed through the system. The resulting mixture was heated to 50° C. and hydrochloric acid (5.6 mL) was added. The mixture was then left under stirring for 4 hours after which water was added and the mixture concentrated under reduced pressure. Sodium chloride was added to the resulting mixture which was then extracted with 4 portions of ethyl acetate. The combined organic phases were distilled under reduced pressure.

Reference: [1]Zingle, Catherine; Kuntz, Lionel; Tritsch, Denis; Grosdemange-Billiard, Catherine; Rohmer, Michel [Bioorganic and medicinal chemistry letters, 2012, vol. 22, # 21, p. 6563 - 6567,5] Zinglé, Catherine; Kuntz, Lionel; Tritsch, Denis; Grosdemange-Billiard, Catherine; Rohmer, Michel [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6563 - 6567]
[2]Coppola, Gary M. [Synthesis, 1984, # 12, p. 1021 - 1023]
[3]Current Patent Assignee: UNI DEGLI STUDI DI MESSINA; UNIV CATANIA - WO2005/82896, 2005, A1 Location in patent: Page/Page column 11-12
[4]Collignon, N.; Fabre, G.; Varlet, J. M.; Savignac, Ph. [Phosphorus and Sulfur and the Related Elements, 1981, vol. 10, p. 81 - 86]
[5]Varlet, J. M.; Fabre, G.; Sauveur, F.; Collignon, N.; Savignac, Ph. [Tetrahedron, 1981, vol. 37, p. 1377 - 1384]
[6]Markey, Sophie J.; Lewis, William; Moody, Christopher J. [Organic Letters, 2013, vol. 15, # 24, p. 6306 - 6308]
[7]Lee, Kyung Seok; Kang, Yong Koo; Yoo, Kyung Ho; Kim, Dong Chan; Shin, Kye Jung; Paik, Young-Sook; Kim, Dong Jin [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 1, p. 231 - 234]
[8]Clare, Brian W.; Ferro, Vito; Skelton, Brian W.; Stick, Robert V.; White, Allan H. [Australian Journal of Chemistry, 1993, vol. 46, # 6, p. 805 - 824]
[9]Pallitsch, Katharina; Rogers, Megan P.; Andrews, Forest H.; Hammerschmidt, Friedrich; McLeish, Michael J. [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4368 - 4374]
[10]Pallitsch, Katharina; Happl, Barbara; Stieger, Christian [Chemistry - A European Journal, 2017, vol. 23, # 62, p. 15655 - 15665]
[11]Dawson; Burger [Journal of the American Chemical Society, 1952, vol. 74, p. 5312]
[12]Tavs,P. [Chemische Berichte, 1967, vol. 100, p. 1571 - 1574]
[13]Razumov,A.I.; Moskva,V.V. [Journal of general chemistry of the USSR, 1964, vol. 34, p. 2612 - 2616][Zhurnal Obshchei Khimii, 1964, vol. 34, p. 2589 - 2594]
[14]Halmann,M. et al. [Journal of the Chemical Society. Perkin transactions II, 1976, p. 1210 - 1213]
[15]Olson, Gary L.; Cheung, Ho-Chuen; Chiang, Elliot; Madison, Vincent S.; Sepinwall, Jerry; et al. [Journal of Medicinal Chemistry, 1995, vol. 38, # 15, p. 2866 - 2879]
[16]Chiacchio, Ugo; Balestrieri, Emanuela; Macchi, Beatrice; Iannazzo, Daniela; Piperno, Anna; Rescifina, Antonio; Romeo, Roberto; Saglimbeni, Monica; Sciortino, M. Teresa; Valveri, Vincenza; Mastino, Antonio; Romeo, Giovanni [Journal of Medicinal Chemistry, 2005, vol. 48, # 5, p. 1389 - 1394]
[17]Friese, Anke; Hell-Momeni, Katja; Zündorf, Ilse; Winckler, Thomas; Dingermann, Theodor; Dannhardt, Gerd [Journal of Medicinal Chemistry, 2002, vol. 45, # 7, p. 1535 - 1542]
[18]Location in patent: experimental part Den Hartog, Tim; Jan Van Dijken, Derk; Minnaard, Adriaan J.; Feringa, Ben L. [Tetrahedron Asymmetry, 2010, vol. 21, # 11-12, p. 1574 - 1584]
[19]Location in patent: experimental part Petroski, Richard J. [Synthetic Communications, 2011, vol. 41, # 1, p. 63 - 66]
[20]Location in patent: experimental part Petroski, Richard J.; Vermillion, Karl; Cosse, Allard A. [Molecules, 2011, vol. 16, # 6, p. 5062 - 5078]
[21]Current Patent Assignee: Dynaction; PROD CHIM AUX ET DE SYNTHESE - US2015/246869, 2015, A1 Location in patent: Paragraph 0093
  • 3
  • [ 2032-35-1 ]
  • [ 122-52-1 ]
  • [ 7598-61-0 ]
YieldReaction ConditionsOperation in experiment
91%
89% at 160 - 165℃;
81% for 4h; Inert atmosphere; Heating; neat (no solvent);
77% at 160℃; for 3h;
74% at 170 - 180℃; for 4h;
72% at 180℃; for 4h;
70% at 160℃; for 3h;
58% at 155℃; for 4h; Dean-Stark; Inert atmosphere; Diethyl 2,2-diethoxyethylphosphonate: Bromoacetaldehyde diethylacetal (19.71 g, 100 mmol, 15.04 mL) was added to triethylphosphite (33.23 g,200 mmol, 34.26 mL). A Dean-Stark head was fitted to the reaction flask and the mixture was heated under argon at 155°C for 4 h. The reaction mixture was cooled to room temperature and afterwards distilled under reduced pressure (80-86°C/0.19 mbar) to obtain the pure phosphonoacetal (14.80 g, 58 mmol, 58%) as a colourless oil. 1H NMR (CDCl3, 400.27 MHz): δ = 4.87 (q, J = 5.7 Hz, 1H, CH), 4.12-4.03 (m, 4H,P- OCH2), 3.63 (qd, J = 7.0 Hz,9.3 Hz, 2H, OCH2), 3.58 (ABX-system, A-part: qd, JAX = 7.0 Hz, JAB 9.3 Hz, 2H, OCH2; B-part: qd, JAX = 7.0 Hz, JAB9.3 Hz, 2H, OCH2), 2.17 (dd, J = 5.7 Hz, 18.6 Hz, 2H, CH2-P), 1.29 (td, J = 7.0 Hz, 0.3 Hz, 3H, CH3), 1.18 (t, J =7.0 Hz, 3H, CH3). 31P NMR (CDCl3, 162.04 MHz): δ = 26.36 (s, product, 96 mol%), 33.65 (s, P(OEt)3, 4 mol%)
58% at 155℃; for 4h; Dean-Stark; Inert atmosphere;
57% Heating;
at 160℃;
at 150 - 160℃;
for 3.5h; Heating;

Reference: [1]Collignon, N.; Fabre, G.; Varlet, J. M.; Savignac, Ph. [Phosphorus and Sulfur and the Related Elements, 1981, vol. 10, p. 81 - 86]
[2]Kouno, Ryoji; Okauchi, Tatsuo; Nakamura, Mitsuharu; Ichikawa, Junji; Minami, Toru [Journal of Organic Chemistry, 1998, vol. 63, # 18, p. 6239 - 6246]
[3]Location in patent: experimental part Dayde, Benedicte; Benzaria, Samira; Pierra, Claire; Gosselin, Gilles; Surleraux, Dominique; Volle, Jean-Noel; Pirat, Jean-Luc; Virieux, David [Organic and Biomolecular Chemistry, 2012, vol. 10, # 17, p. 3448 - 3454]
[4]Clare, Brian W.; Ferro, Vito; Skelton, Brian W.; Stick, Robert V.; White, Allan H. [Australian Journal of Chemistry, 1993, vol. 46, # 6, p. 805 - 824]
[5]Burilov; Knyazeva; Sadykova; Pudovik; Habicher; Baier; Konovalov [Russian Chemical Bulletin, 2007, vol. 56, # 6, p. 1144 - 1148]
[6]Burilov; Volodina; Popova; Gazizov; Knyazeva; Pudovik; Habicher; Konovalov [Russian Journal of General Chemistry, 2006, vol. 76, # 3, p. 412 - 416]
[7]Lee, Kyung Seok; Kang, Yong Koo; Yoo, Kyung Ho; Kim, Dong Chan; Shin, Kye Jung; Paik, Young-Sook; Kim, Dong Jin [Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 1, p. 231 - 234]
[8]Pallitsch, Katharina; Rogers, Megan P.; Andrews, Forest H.; Hammerschmidt, Friedrich; McLeish, Michael J. [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4368 - 4374]
[9]Pallitsch, Katharina; Happl, Barbara; Stieger, Christian [Chemistry - A European Journal, 2017, vol. 23, # 62, p. 15655 - 15665]
[10]Jones, Raymond C. F.; Bhalay, Gurdip; Carter, Paul A. [Journal of the Chemical Society. Perkin transactions I, 1993, # 15, p. 1715 - 1716]
[11]Tavs,P. [Chemische Berichte, 1967, vol. 100, p. 1571 - 1574]
[12]Razumov,A.I.; Moskva,V.V. [Journal of general chemistry of the USSR, 1964, vol. 34, p. 2612 - 2616][Zhurnal Obshchei Khimii, 1964, vol. 34, p. 2589 - 2594] Dawson; Burger [Journal of the American Chemical Society, 1952, vol. 74, p. 5312] Sturz, G.; Clement, J. C.; Daniel, A.; Molinier, J.; Lenzi, M. [Bulletin de la Societe Chimique de France, 1981, vol. 1, # 5-6, p. 161 - 172]
[13]Iorga, Bogdan; Eymery, Frederic; Mouries, Virginie; Savignac, Philippe [Tetrahedron, 1998, vol. 54, # 49, p. 14637 - 14677]
[14]Friese, Anke; Hell-Momeni, Katja; Zündorf, Ilse; Winckler, Thomas; Dingermann, Theodor; Dannhardt, Gerd [Journal of Medicinal Chemistry, 2002, vol. 45, # 7, p. 1535 - 1542]
  • 4
  • [ 50-70-4 ]
  • [ 7598-61-0 ]
  • [ 75041-66-6 ]
YieldReaction ConditionsOperation in experiment
97.8% With hydrogenchloride for 192h;
  • 6
  • [ 7598-61-0 ]
  • [ 111-27-3 ]
  • [ 134902-36-6 ]
YieldReaction ConditionsOperation in experiment
30% With 0.5 N Et4NCl4 In acetonitrile at -20℃; cathodic electrolysis (2.00 F/mole, vitreous carbon electrode);
  • 7
  • [ 109-80-8 ]
  • [ 7598-61-0 ]
  • [1,3]Dithian-2-ylmethyl-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With boron trifluoride diethyl etherate In dichloromethane for 12h; Ambient temperature;
  • 8
  • [ 7598-61-0 ]
  • (E)-Diethyl 2-ethoxyethenylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h;
80% With toluene-4-sulfonic acid In toluene for 6h; Inert atmosphere; Reflux;
  • 9
  • [ 7598-61-0 ]
  • [ 108-46-3 ]
  • 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetrakis[((ethoxy)(hydroxy)phosphoryl)methyl]pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With sulfuric acid In ethanol; water at 20 - 50℃;
59% With hydrogenchloride In ethanol; water at 20 - 50℃; for 2h;
56% With hydrogenchloride In ethanol at 20 - 60℃; for 11h;
  • 10
  • [ 7598-61-0 ]
  • [ 107-18-6 ]
  • [ 850255-64-0 ]
YieldReaction ConditionsOperation in experiment
77% With toluene-4-sulfonic acid In benzene for 34.5h; Heating;
  • 11
  • [ 7598-61-0 ]
  • [ 151-10-0 ]
  • [2,2-bis-(2,4-dimethoxy-phenyl)-ethyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 2h;
  • 12
  • [ 7598-61-0 ]
  • [ 10357-84-3 ]
  • 4,6,10,12,16,18,22,24-octahydroxy-2,8,14,20-tetrakis[(dihydroxyphosphoryl)methyl]-5,11,17,23-tetraazapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene tetrahydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With hydrogenchloride In ethanol at 70 - 80℃; for 168h;
  • 13
  • [ 7598-61-0 ]
  • ((E)-2-Allyloxy-vinyl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 77 percent / TsOH / benzene / 34.5 h / Heating 2: 100 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C
  • 14
  • [ 7598-61-0 ]
  • diethyl (Z)-2-allyloxy-1-(iodo)-vinylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 77 percent / TsOH / benzene / 34.5 h / Heating 2.1: 100 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 3.1: LDA / tetrahydrofuran / 0.83 h / -78 °C 3.2: CuBr*SMe2 / tetrahydrofuran / 0.75 h / -78 °C 3.3: 74 percent / I2 / tetrahydrofuran / 3 h / -78 °C
  • 15
  • [ 7598-61-0 ]
  • [ 20061-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 33.91 g / 2percent aq. HCl / Heating 2: 48.52 percent / methanol / 0.17 h / 20 °C
  • 16
  • [ 7598-61-0 ]
  • [ 57415-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 96 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature, 3 h 3: 99 percent / H2 / Pd/C / methanol / 48 h / Ambient temperature 4: 80 percent / NaOEt / tetrahydrofuran / 0.17 h / Ambient temperature
  • 17
  • [ 7598-61-0 ]
  • [ 98934-49-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 1.5 h 3: 83 percent / NH2NH2*H2O / ethanol / Heating
  • 18
  • [ 7598-61-0 ]
  • [ 212701-39-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 91 percent / LDA, I2, CuBr*SMe2 / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature, 1.5 h
  • 19
  • [ 7598-61-0 ]
  • [ 212701-59-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 96 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature, 3 h 3: 99 percent / H2 / Pd/C / methanol / 48 h / Ambient temperature
  • 20
  • [ 7598-61-0 ]
  • {1-[1-Ethoxy-meth-(E)-ylidene]-but-3-enyl}-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 24 h
  • 21
  • [ 7598-61-0 ]
  • [ 212701-31-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 96 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature, 3 h
  • 22
  • [ 7598-61-0 ]
  • (E)-2-(Diethoxy-phosphoryl)-3-ethoxy-acrylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 1.5 h
  • 23
  • [ 7598-61-0 ]
  • [(E)-1-(tert-Butyl-dimethyl-silanyl)-2-ethoxy-vinyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 75 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature, 13 h
  • 24
  • [ 7598-61-0 ]
  • diethyl 1-phenyl-2-ethoxyvinylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 5 h
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 2.5 h
  • 25
  • [ 7598-61-0 ]
  • (3-Phenyl-isoxazol-4-yl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 1.5 h 3: 61 percent / NH2OH*HCl, pyridine / ethanol / Heating
  • 26
  • [ 7598-61-0 ]
  • (2-Oxy-isoquinolin-4-yl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 4 h 3: 85 percent / NH2OH*HCl, Et3N / ethanol / 60 h / Ambient temperature
  • 27
  • [ 7598-61-0 ]
  • [(E)-2-Ethoxy-1-(2-formyl-phenyl)-vinyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 4 h
  • 28
  • [ 7598-61-0 ]
  • {1-[1-Ethoxy-meth-(E)-ylidene]-3-phenyl-prop-2-ynyl}-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 91 percent / LDA, I2, CuBr*SMe2 / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature, 1.5 h 3: 79 percent / PdCl2, PPh3, CuI, Et3N / tetrahydrofuran / 12 h / Ambient temperature
  • 29
  • [ 7598-61-0 ]
  • [ 212701-53-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 1.5 h
  • 30
  • [ 7598-61-0 ]
  • [(E)-1-(2-Acetyl-phenyl)-2-ethoxy-vinyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 1.) LDA, Bu3SnCl, 2.) Pd(PPh3)4, CuCN / 1.) THF, -78 deg C, 1 h; -78 deg C to room temperature, 5 h, 2.) toluene, reflux, 10 h
  • 31
  • [ 7598-61-0 ]
  • ((Z)-2-Ethylsulfanyl-1-trimethylsilanyl-vinyl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 96 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature, 3 h 3: 20 percent / EtSLi / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) -78 deg C to room temperature, 3 h
  • 32
  • [ 7598-61-0 ]
  • ((E)-2-Ethylsulfanyl-1-trimethylsilanyl-vinyl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 97 percent / LDA / tetrahydrofuran / 1 h / -78 °C 2: 96 percent / LDA / tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C to room temperature, 3 h 3: 76 percent / EtSLi / tetrahydrofuran / 1.) -78 deg C, 10 min, 2.) -78 deg C to room temperature, 3 h
  • 33
  • [ 7598-61-0 ]
  • [ 79782-60-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq. HCl / 0.75 h / Heating 2: 38.6 g / methanol / 1 h / 0 °C
  • 34
  • [ 7598-61-0 ]
  • [ 67264-30-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / acid 2: 28 percent / NaBH3CN, 4 M HCl / ethanol; methanol / 84 h / 25 °C
Multi-step reaction with 2 steps 1: hydrogenchloride / water / Inert atmosphere 2: sodium cyanoborohydride / methanol / 20 °C / Inert atmosphere
  • 35
  • [ 7598-61-0 ]
  • [ 995-32-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: ion-exchange resin + form> 2: NEt3 3: 1 h / 130 °C 4: NaNH2 / liquid ammonia / 2 h / -35 °C 5: H2 / Raney-Ni / ethanol / 70 °C
  • 36
  • [ 7598-61-0 ]
  • [ 14437-88-8 ]
  • TRANS-4-(BROMOMETHYL)-2-(DIETHYLOXY PHOSPHINOYLMETHYL)-1,3-DIOXOLANE [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With PTSA; sodium hydrogencarbonate In toluene 92 (2R,4R) and (2S,4R)-4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane STR131 EXAMPLE 92 (2R,4R) and (2S,4R)-4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane STR131 To a solution of diethylphosphonoacetaldehyde diethylacetal (4.20 g, 16.5 mmol) and (2R)-3-bromo-1,2-propanediol (example 90) (3.00 g, 19.4 mmol, 1.2 eq.) in toluene (30 mL) was added pTSA (few crystals). The mixture was stirred at reflux for 50 hr. After, the solution was cooled to room temperature, and a saturated solution of sodium bicarbonate was added, and the aqueous phase was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude material was pure by TLC and NMR, and gave 5.06 g of the compound in a 97% yield. 1 H NMR (300 MHz, CDCl3) δ: 1.33 (t, 6H, J=7.0 Hz, CH3), 2.20 (dd, 0.66H, J=5.4 Hz, 2 JHP =18 Hz, CH2 P for trans), 2.25 (dd, 1.33H, J=5.2 Hz, 2 JHP =18.7 Hz, CH2 P for cis), 3.32 (2dd, 1H, J=7.9 Hz, 10.2 Hz, CHA HB Br), 3.42 and 3.48 (2dd, 1H, J=4.8 Hz, 10.2 Hz, CHA HB Br), 3.74 (dd, 0.33H, J=6.4 Hz, 8.8 Hz, H-5a for trans), 3.99 (d, 1.33H, J=5.2 Hz, H-5 for cis), 4.13 (m, 4H, CH2), 4.26 (dd, 0.33H, J=6.4 Hz, 8.8 Hz, H-5b for trans), 4.35 (m, 1H, H-4), 5.24 (dt, 0.66H, J=5.2 Hz, 3 JHP =4.7 Hz, H-2 for cis), 5.37 (dt, 0.33H, J=5.2 Hz, 3 JHP =5.2 Hz, H-2 for trans).
  • 37
  • [ 7598-61-0 ]
  • [ 191859-34-4 ]
  • [ 211038-24-3 ]
YieldReaction ConditionsOperation in experiment
87% With PTSA; sodium hydrogencarbonate In toluene 129 Cis and Trans 5-(t-Butyldiphenylsilyloxymethyl)-2-(Diethyloxyphosphinoylmethyl)-1,3-Oxathiolane STR176 EXAMPLE 129 Cis and Trans 5-(t-Butyldiphenylsilyloxymethyl)-2-(Diethyloxyphosphinoylmethyl)-1,3-Oxathiolane STR176 To a solution of diethylphosphonoacetaldehyde diethylacetal (12.23 g, 48.1 mmol, 1.2 eq.) and t-butyldiphenylsilyloxy-3-mercapto-2-propanol (13.63 g, 38.1 mmol, 1.2 eq.) in toluene (500 mL) was added PTSA (0.73 g, 3.8 mmol, 0.1 eq.). The mixture was stirred at reflux for 72 hr and was cooled to room temperature. A saturated solution of sodium bicarbonate was added and the aqueous phase was extracted with dichloromethane. The organic phase was dried with anhydrous magnesium sulphate and evaporated under reduced pressure. The crude material was purified by flash chromatography with ethyl acetate:hexane (2:1), and gave 16.31 g of the compound in a 87% yield. 1 H NMR (300 MHz, CDCl3) δ: 7.64 (m, 4H, Ar-H), 7.38 (m, 6H, Ar-H), 5.43 (dd, 0.35H, J=12 Hz, J=6 Hz, H-2), 5.34 (dd, 0.65H, J=12 Hz, J=6 Hz, H-2), 4.39 (q, 0.35H, J=6 Hz, H-5), 4.09 (m, 4H, CH2 and 0.65H, H-5), 3.86 (dd, 0.65H, J=11 Hz, J=5 Hz, CHA CHB O), 3.75(dd, 0.65H, J=11 Hz, J=6 Hz, CHA CHB O), 3.72 (d, 0.35H, J=5 Hz, CHA CHB O), 3.71 (d, 0.35H, J=6 Hz, CHA CHB O), 3.09 (m, 1.35H, H-4), 2.92 (dd, 0.65H, J=10 Hz, J=9 Hz, H-4), 2.44 (m, 1H, CH2 P), 2.25 (m, 1H, CH2 P), 1.28 (m, 6H, CH3), 1.03 (s, 9H, 3 t-butyl).
  • 38
  • [ 4704-77-2 ]
  • [ 7598-61-0 ]
  • [ 211037-75-1 ]
YieldReaction ConditionsOperation in experiment
96% With PTSA; sodium hydrogencarbonate In toluene 83 Cis and Trans 4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane STR116 EXAMPLE 83 Cis and Trans 4-(Bromomethyl)-2-(Diethoxyphosphinoylmethyl)-1,3-Dioxolane STR116 To a solution of diethylphosphonoacetaldehyde diethylacetal (15.00 g, 59.0 mmol) and 3-bromo-1,2-propanediol (11.00 g, 71.0 mmol, 1.2 eq.) in toluene (60 mL) was added pTSA (few cristals). The mixture was stirred at reflux for 72 hr and was cooled to room temperature. A saturated solution of sodium bicarbonate was added and the aqueous phase was extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulphate and evaporated under reduced pressure. The crude material was pure by TLC and NMR and gave 17.93 g of the compound in a 96% yield. 1 H NMR (300 MHz, CDCl3) δ: 1.33 (t, 6H, J=7.0 Hz, CH3), 2.20 (dd, 0.66H, J=5.4 Hz, 2 JHP =17 Hz, CH2 P for trans), 2.25 (dd, 1.33H, J=5.2 Hz, 2 JHP =18.7 Hz, CH2 P for cis), 3.32 (dd, 1H, J=7.9 Hz, 10.2 Hz, CHA HB Br), 3.42 and 3.48 (2dd, 1H, J=4.8 Hz, 10.2 Hz, CHA HB Br), 3.74 (dd, 0.33H, J=6.4 Hz, 8.8 Hz, H-5a for trans), 3.98 (d, 1.33H, J=5.2 Hz, H-5 for cis), 4.13 (m, 4H, CH2), 4.26 (dd, 0.33H, J=6.2 Hz, 8.7 Hz, H-5b for trans), 4.35 (m, 1H, H-4), 5.24 (dt, 0.66H, J=5.2 Hz, 3 JHP =4.7 Hz, H-2 for cis), 5.37 (dt, 0.33H, J=5.2 Hz, 3 JHP =5.2 Hz, H-2 for trans).
  • 39
  • [ 7598-61-0 ]
  • [ 1576-35-8 ]
  • [ 591235-28-8 ]
YieldReaction ConditionsOperation in experiment
81% With hydrogenchloride; water at 75℃; for 2h; 113.113a Example 113; rac-(2R,3S)-2-methyl-3-phenyl-2-(1H-pyrazol-5-yl)-2,3-dihydro-1H-indene-5-carbonitrile; (113a) A solution of diethylphosphorylacetalaldehyde diethylacetal (11.30 mL, 1.05 eq) and p-toluenesulfonyl hydrazide (8.27 g, 44.4 mmol) in 0.1 N aqueous HCl (20 mL) was heated at 75° C. for 2 h then cooled to room temperature. A crystalline solid was formed and collected by filtration. The solid was washed with cold water and ether to give the desired hydrazone intermediate (12.58 g, 81%).
  • 40
  • [ 102-54-5 ]
  • [ 7598-61-0 ]
  • diethyl (E)-ferrocenylvinylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With methanesulfonic acid In further solvent(s) ligand (2 equiv.) added in one portion at room temp. to stirred soln. offerrocene in MeSO3H; stirred for 2 h; poured onto water; extd. with CH2Cl2; isolated by column chromy.; elem. anal.;
58% With triflic acid In dichloromethane triflic acid added at room temp. to stirred soln. of ferrocene in CH2Cl2; stirred for 2 min; ligand (2 equiv.) added in one portion; stirred for2 h; poured onto ice-water; extd. with CH2Cl2; evapd. to dryness; treated with water; extd. with hexanes; column chromd.; elem. anal.;
  • 41
  • [ 7598-61-0 ]
  • [ 131286-55-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / water; acetone / 96 h / 25 °C / Inert atmosphere 2: magnesium sulfate / 48 h / 25 °C / Inert atmosphere
  • 42
  • [ 7598-61-0 ]
  • [ 1369960-64-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / toluene / 6 h / Inert atmosphere; Reflux 2: toluene-4-sulfonic acid / toluene / Inert atmosphere; Reflux 3: iodine / dichloromethane / -30 - 20 °C / Inert atmosphere 4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 5 h / 70 °C / Inert atmosphere
  • 43
  • [ 7598-61-0 ]
  • [ 1369960-65-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / toluene / 6 h / Inert atmosphere; Reflux 2: toluene-4-sulfonic acid / toluene / Inert atmosphere; Reflux 3: iodine / dichloromethane / -30 - 20 °C / Inert atmosphere 4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 5 h / 70 °C / Inert atmosphere
  • 44
  • [ 7598-61-0 ]
  • [ 1369960-66-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / toluene / 6 h / Inert atmosphere; Reflux 2: toluene-4-sulfonic acid / toluene / Inert atmosphere; Reflux 3: iodine / dichloromethane / -30 - 20 °C / Inert atmosphere 4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 5 h / 70 °C / Inert atmosphere
  • 45
  • [ 1445-75-6 ]
  • [ 7598-61-0 ]
  • [ 1420879-41-9 ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: diisopropyl methanephosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: diethyl phosphonoacetaldehyde diethyl acetal In tetrahydrofuran; hexane at -78 - 20℃; for 3h; Inert atmosphere; General procedure for the preparation of 1,1­-bisphosphorus compounds General procedure: A solution of methylphosphonate (2 mmol, 2 equiv) in anhydrous THF (3 ml) is cooled down to -­78°C under nitrogen and n-­BuLi (2.2 mmol, 2.5 M in hexane, 0.9 mL, 2.2 equiv) is added dropwise. The solution is stirred at -­78°C for 1 hour then the phosphorus electrophile P(O)(OR) (1 mmol, 1 equiv) in THF (1 ml) is added via a syringe. After 1 hour, the solution is warmed up to rt then stirred for an additional 2 hours.
  • 46
  • [ 7598-61-0 ]
  • [ 135-77-3 ]
  • [ 1431862-17-7 ]
YieldReaction ConditionsOperation in experiment
60% With trifluorormethanesulfonic acid In acetonitrile at 0 - 20℃; for 24h;
  • 47
  • [ 7598-61-0 ]
  • [ 1497420-33-3 ]
  • [ 1497420-34-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 2 h / Reflux 2: pyridine / dichloromethane / 2 h / 20 °C
  • 48
  • diphenyl(trifluoromethanesulfonato)-λ3-iodane [ No CAS ]
  • [ 7598-61-0 ]
  • [ 1616475-91-2 ]
YieldReaction ConditionsOperation in experiment
86% With 2,6-di-tert-butyl-pyridine; copper(l) chloride In dichloromethane at 40℃; Schlenk technique; Inert atmosphere;
  • 49
  • [ 7598-61-0 ]
  • mesitylstyrenyliodonium triflate [ No CAS ]
  • (E)-ethyl styryl (2,2-diethoxyethyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With 2,6-di-tert-butyl-pyridine; copper(I) thiophene-2-carboxylate In dichloromethane at 50℃; for 10h; Inert atmosphere; Sealed tube; 3. General procedure for the copper-catalyzed oxygen-alkenylation of dialkyl phosphonates General procedure: CuTC (0.02 mmol, 0.10 equiv), the corresponding alkenyl(aryl)iodonium salt 2 (0.6 mmol, 2 equiv) and a stirring bar were charged in a sealed tube. A solution of phosphonate 1 (0.2 mmol, 1 equiv) in dry dichloromethane (2 ml) and 2,6-di-tert-butylpyridine (0.22 mmol, 1 equiv) was added and the resulting mixture was stirred at 50 °C under an argon atmosphere for 16 h. After this time, the reaction was quenched by addition of saturated aqueous solution of NH4Cl (10 ml) and extracted with CH2Cl (2 × 10 ml). The organic layer was dried over Na2SO4, filtered and solvent was removed under vacuum. The final product was purified by column chromatography on silica gel using n-hexane/AcOEt (1:1) as eluent. 4
  • 50
  • [ 7598-61-0 ]
  • mesitylstyrenyliodonium triflate [ No CAS ]
  • (E)-ethyl styryl (2,2-diethoxyethyl)phosphonate [ No CAS ]
  • ethyl (E)-styryl ((E)-2-ethoxyvinyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,6-di-tert-butyl-pyridine; copper(I) thiophene-2-carboxylate In dichloromethane at 50℃; for 18h; Inert atmosphere; Sealed tube; 3. General procedure for the copper-catalyzed oxygen-alkenylation of dialkyl phosphonates General procedure: CuTC (0.02 mmol, 0.10 equiv), the corresponding alkenyl(aryl)iodonium salt 2 (0.6 mmol, 2 equiv) and a stirring bar were charged in a sealed tube. A solution of phosphonate 1 (0.2 mmol, 1 equiv) in dry dichloromethane (2 ml) and 2,6-di-tert-butylpyridine (0.22 mmol, 1 equiv) was added and the resulting mixture was stirred at 50 °C under an argon atmosphere for 16 h. After this time, the reaction was quenched by addition of saturated aqueous solution of NH4Cl (10 ml) and extracted with CH2Cl (2 × 10 ml). The organic layer was dried over Na2SO4, filtered and solvent was removed under vacuum. The final product was purified by column chromatography on silica gel using n-hexane/AcOEt (1:1) as eluent. 4
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