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Journal articles on the topic 'Dimethyl phosphoramidate'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Shtamburg, V. G., E. A. Klots, V. V. Shtamburg, et al. "Dialkyl-N-alkoxy-N-(4-toluenesulfonyl)phosphoramidates: synthesis and structure." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 2 (April 2025): 33–44. https://doi.org/10.32434/0321-4095-2025-159-2-33-44.

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This study investigates the reaction between N-alkoxy-N-chloro-4-toluenesulfonamides and N-chloro-N-(methoxy)methanesulfonamide with trialkyl phosphites, resulting in the formation of dialkyl N-alkoxy-N-(4-toluenesulfonyl)phosphoroamidates and dialkyl N-methoxy-N-methanesulfonylphosphoroamidates, respectively. The resulting dialkyl N-alkoxy-N-(4-toluenesulfonyl)phosphoramidates and N-alkoxy-N-methanesulfonylphosphoramidates are identified as products of nucleophilic substitution at the amide nitrogen atom. The structures of these compounds have been confirmed by ¹H, ³¹P, and ¹³C NMR spectrosco

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2

Seyda, Aydogdu, and Hatipoglu Arzu. "Theoretical investigation on the kinetics of dimethyl phosphoramidate with hydroxyl radicals." Journal of Indian Chemical Society Vol. 96, Sep 2019 (2019): 1117–22. https://doi.org/10.5281/zenodo.5643205.

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Department of Chemistry, Yildiz Technical University, 34220 Istanbul, Turkey <em>E-mail</em>: hatiparzu@yahoo.com <em>Manuscript received online 26 April 2019, revised and accepted 20 July 2019</em> In this paper the reaction kinetics of dimethyl phosphoramidate with hydroxyl radical was investigated with Density Functional Theory. Geometry optimization and energy calculations of the reactants, the pre-reactive complexes, the transition states and the products were performed at the B3LYP/6-31G(d) basis set. The water effect was computed by using CPCM as the solvation model. Rate constants of a

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3

Gholivand, Khodayar, Azadeh Tadjarodi, and Seik Weng Ng. "N,N-Dimethyl-N′,N′′-bis(4-methylphenyl)phosphoramidate." Acta Crystallographica Section E Structure Reports Online 58, no. 2 (2002): o200—o201. http://dx.doi.org/10.1107/s1600536802001587.

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4

Plessis, Michael P., Tomasz A. Modro, and Luigi R. Nassimbeni. "Crystal and molecular structures of two polymorphic forms of dimethyl-N-(2-ethylphenyl)-phosphoramidate (I) and dimethyl-N-(2,6-dimethylphenyl)-phosphoramidate (II)." Journal of Crystallographic and Spectroscopic Research 15, no. 6 (1985): 663–78. http://dx.doi.org/10.1007/bf01164779.

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5

Struhatska, Mariia B., Nataliia S. Kariaka, Vladimir M. Amirkhanov, Viktoriya V. Dyakonenko, and Maksym Seredyuk. "Crystal structure and Hirshfeld surface analysis of the anionic tetrakis-complex of lanthanum(III) NMe₄LaL ₄ with the CAPh-ligand dimethyl (2,2,2-trichloroacetyl)phosphoramidate." Acta Crystallographica Section E Crystallographic Communications 77, no. 12 (2021): 1307–10. http://dx.doi.org/10.1107/s2056989021011750.

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The anionic tetrakis-complex of lanthanum(III) NMe4LaL 4 with the CAPh-ligand dimethyl (2,2,2-trichloroacetyl)phosphoramidate (HL), namely, tetramethylammonium tetrakis{2,2,2-trichloro-1-[(dimethoxyphosphoryl)imino]ethanolato}lanthanum(III), (C4H12N)[La(C4H6Cl3NO4P)4], has been synthesized, crystallized and structurally characterized by X-ray diffraction. The lanthanide ion is surrounded by four anionic, bis-chelating CAPh ligands forming the complex anion with a coordination number of eight for La3+ and NMe4 + as the counter-ion. The coordination polyhedron of the La3+ ion was interpreted as

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6

Kahn, Brian A., John P. Damicone, Kenneth E. Jackson, James E. Motes, and Mark E. Payton. "Comparing Chitin-urea to Other Materials for Control of Northern Root-knot Nematode on Paprika Pepper." HortScience 37, no. 6 (2002): 948–49. http://dx.doi.org/10.21273/hortsci.37.6.948.

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Nine nematicide treatments were evaluated from 1993 through 1995 in field experiments on paprika pepper (Capsicum annuum L.). Materials tested included a chitinurea soil amendment and six chemicals: fosthiazate, carbofuran, aldicarb, oxamyl, fenamiphos, and 1,3-dichloropropene (1,3-D). Stands at harvest were increased relative to the control by chitin-urea, fosthiazate, and 1,3-D, but only fosthiazate increased marketable fruit yield relative to the control. Aldicarb reduced preharvest nematode populations relative to the control, but aldicarb did not result in a significant fruit yield increa

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7

Wang, Huaifang, Yingli Cai, Zhiming Jiang, Shengnan Guo, and Ping Zhu. "Synthesis of a phosphoramidate flame retardant and its flame retardancy on cotton fabrics." e-Polymers 20, no. 1 (2020): 550–60. http://dx.doi.org/10.1515/epoly-2020-0059.

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AbstractA phosphoramidate flame retardant (dimethyl N,N-bis(2-hydroxyletheyl)phosphoramidate, DMBHP) was synthesized and applied to cotton fabrics for enhancing the flame retardancy. The structure of DMBHP was characterized by FT-IR and NMR. The flame retardancy and combustion behavior of the treated cotton fabrics were evaluated using the vertical flammability test (VFT), limiting oxygen index (LOI), and the cone calorimetric test. Moreover, to further analyze the flame retardant action of DMBHP in cotton fabrics, thermal degradability of the treated fabrics, as well as the chemical structure

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8

Ko, Seongjae, Ayaka Matsuoka, Wenting Chen, et al. "Multifunctional Cyclic Phosphoramidate Solvent for Safe Lithium-Ion Batteries." ECS Meeting Abstracts MA2024-02, no. 10 (2024): 4911. https://doi.org/10.1149/ma2024-02104911mtgabs.

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To enhance the overall safety of electronic devices and energy storage systems, the development of functional electrolytes that improve the thermal stability of rechargeable batteries is of utmost importance. Here, we report a novel cyclic phosphoramidate, 2-(N,N-dimethylamino)-1,3,2-dioxaphospholane-2-oxide (DMAP), which has been newly designed and synthesized as a multifunctional solvent for safe Li-ion batteries.1 Its unique molecular structure, incorporating an amine moiety into a five-membered cyclic phosphate, provides both high electrochemical and thermal benefits: (i) a stable DMAP-der

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9

Liang, Shuyu, Patrick Hemberger, Joëlle Levalois‐Grützmacher, Hansjörg Grützmacher, and Sabyasachi Gaan. "Probing Phosphorus Nitride (P≡N) and Other Elusive Species Formed upon Pyrolysis of Dimethyl Phosphoramidate." Chemistry – A European Journal 23, no. 23 (2017): 5595–601. http://dx.doi.org/10.1002/chem.201700402.

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10

Vilanova, E., M. K. Johnson, and J. L. Vicedo. "Interaction of some unsubstituted phosphoramidate analogs of methamidophos (O,S-dimethyl phosphorothioamidate) with acetylcholinesterase and neuropathy target esterase of hen brain." Pesticide Biochemistry and Physiology 28, no. 2 (1987): 224–38. http://dx.doi.org/10.1016/0048-3575(87)90021-6.

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11

Johnson, M. K., E. Vilanova, and D. J. Read. "Biochemical and clinical tests of the delayed neuropathic potential of some O-alkylO-dichlorophenyl phosphoramidate analogues of methamidophos (O,S-dimethyl phosphorothioamidate)." Toxicology 54, no. 1 (1989): 89–100. http://dx.doi.org/10.1016/0300-483x(89)90081-4.

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12

Zamani, Hassan Ali, Mohammad Reza Ganjali, Parviz Norouzi, Azadeh Tadjarodi, and Encyeh Shahsavani. "Determination of terbium(III) ions in phosphate rock samples by a Tb3+–PVC membrane sensor based on N, N-Dimethyl-N′, N″-bis(4-methoxyphenyl)phosphoramidate." Materials Science and Engineering: C 28, no. 8 (2008): 1489–94. http://dx.doi.org/10.1016/j.msec.2008.04.002.

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13

Ovchynnikov, Vladimir. "N,N′-Dimethyl-N′′-(trichloroacetyl)phosphoramide." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (2013): o1759. http://dx.doi.org/10.1107/s1600536813030389.

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In the title compound, C4H9Cl3N3O2P or CCl3C(O)NHP(O)(NHCH3)2, the P atom has a strongly distorted tetrahedral geometry due to the formation of intermolecular strong hydrogen bonds involving the N atoms. In the crystal, N—H...O=P and N—H...O=C hydrogen bonds connect the molecules into a two-dimensional array parallel to (100). An intramolecular P...O contact [P...O = 2.975 (3) Å] is observed. The CCl3group is rotationally disordered, with occupancies of 0.60 (3) and 0.40 (3)

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14

Wu, Jian, Lee Bishop, Jiatong Guo, and Zhongwu Guo. "An Investigation of the Reactions between Azido Alcohols and Phosphoramidites." Synlett 30, no. 03 (2019): 348–52. http://dx.doi.org/10.1055/s-0037-1611461.

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The reactions of several β-, γ-, and δ-azido alcohols with dibenzyl and dimethyl N,N-diisopropylphosphoramidites were examined. Detailed analysis of the intermediates and products formed from the reactions under different conditions provided useful information to gain insights into their mechanisms involving intramolecular Staudinger reaction, as well as the structure–reactivity relationships of both substrates. The reactions of γ- and δ-azido alcohols with dibenzyl N,N-diisopropylphosphoramidite could produce 6- and 7-membered cyclic phosphoramidates, thereby providing a new synthetic method

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15

Krasheninina, Olga A., Veniamin S. Fishman, Alexander A. Lomzov, Alexey V. Ustinov, and Alya G. Venyaminova. "Postsynthetic On-Column 2′ Functionalization of RNA by Convenient Versatile Method." International Journal of Molecular Sciences 21, no. 14 (2020): 5127. http://dx.doi.org/10.3390/ijms21145127.

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We report a universal straightforward strategy for the chemical synthesis of modified oligoribonucleotides containing functional groups of different structures at the 2′ position of ribose. The on-column synthetic concept is based on the incorporation of two types of commercial nucleotide phosphoramidites containing orthogonal 2′-O-protecting groups, namely 2′-O-thiomorpholine-carbothioate (TC, as “permanent”) and 2′-O-tert-butyl(dimethyl)silyl (tBDMS, as “temporary”), to RNA during solid-phase synthesis. Subsequently, the support-bound RNA undergoes selective deprotection and follows postsynt

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16

Sontakke, Vyankat A., Harri Lönnberg, and Mikko Ora. "4-(Acetylthio)-2,2-dimethyl-3-oxobutyl and 4-(tert-Butyldisulfanyl)-2,2-dimethyl-3-oxobutyl as Protecting Groups for Nucleoside 5′-Phosphoramidates Derived fromL-Alanine Methyl Ester." European Journal of Organic Chemistry 2015, no. 22 (2015): 5004–12. http://dx.doi.org/10.1002/ejoc.201500531.

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17

Kurihara, Kazunori, Yasunori Yamamoto та Norio Miyaura. "A chiral bidentate phosphoramidite (Me-BIPAM) for Rh-catalyzed asymmetric hydrogenation of α-dehydroamino esters, enamides, and dimethyl itaconate". Tetrahedron Letters 50, № 26 (2009): 3158–60. http://dx.doi.org/10.1016/j.tetlet.2008.12.086.

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18

Jiang, Yongying, and Longqin Hu. "N-(2,2-Dimethyl-2-(2-nitrophenyl)acetyl)-4-aminocyclophosphamide as a potential bioreductively activated prodrug of phosphoramide mustard." Bioorganic & Medicinal Chemistry Letters 18, no. 14 (2008): 4059–63. http://dx.doi.org/10.1016/j.bmcl.2008.05.099.

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19

Sontakke, Vyankat A., Harri Loennberg, and Mikko Ora. "ChemInform Abstract: 4-(Acetylthio)-2,2-dimethyl-3-oxobutyl and 4-(tert-Butyldisulfanyl)-2,2-dimethyl-3-oxobutyl as Protecting Groups for Nucleoside 5′-Phosphoramidates Derived from L-Alanine Methyl Ester." ChemInform 46, no. 47 (2015): no. http://dx.doi.org/10.1002/chin.201547196.

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20

Rosenberry, Terrone L. "Solvent Deuterium Oxide Isotope Effects on the Reactions of Organophosphorylated Acetylcholinesterase." Molecules 25, no. 19 (2020): 4412. http://dx.doi.org/10.3390/molecules25194412.

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Organophosphates (OPs) are esters of substituted phosphates, phosphonates or phosphoramidates that react with acetylcholinesterase (AChE) by initially transferring the organophosphityl group to a serine residue in the enzyme active site, concomitant with loss of an alcohol or halide leaving group. With substituted phosphates, this transfer is followed by relatively slow hydrolysis of the organophosphoryl AChE, or dephosphorylation, that is often accompanied by an aging reaction that renders the enzyme irreversibly inactivated. Aging is a dealkylation that converts the phosphate triester to a d

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21

Kruck, Matthias, M. Paz Munoz, Hannah L Bishop, et al. "BINOL-3,3′-TrifloneN,N-Dimethyl Phosphoramidites: Through-Space19F,31P Spin-Spin Coupling with a Remarkable Dependency on Temperature and Solvent Internal Pressure." Chemistry - A European Journal 14, no. 26 (2008): 7808–12. http://dx.doi.org/10.1002/chem.200800825.

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22

Sopchik, Alan E., S. Matthew Cairns, and Wesley G. Bentrude. "17O NMR of diastereomeric 3′,5′-cyclic thymidine methyl phosphates, methylphosphonates, and N,N-dimethyl phosphoramidates. Phosphorus configuration of P-chiral [17O, 18O]-nucleoside phosphate diesters." Tetrahedron Letters 30, no. 10 (1989): 1221–24. http://dx.doi.org/10.1016/s0040-4039(00)72720-1.

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23

Bhattacharya, B. K., та G. R. Revankar. "A Facile Synthesis of the Phosphoramidites of 2-N-Methyl-2′-deoxy (or 2′-O-allyl)-ψ-isocytidine, 1, 3-Dimethyl-2′-deoxy-ψ-uridine andN1-Methyl-2′-O-allyl-ψ-uridine as Synthons Suitable for Oligonucleotide Synthesis". Nucleosides and Nucleotides 13, № 8 (1994): 1721–38. http://dx.doi.org/10.1080/15257779408009476.

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24

BHATTACHARYA, B. K., та G. R. REVANKAR. "ChemInform Abstract: A Facile Synthesis of the Phosphoramidites of 2-N-Methyl-2′-deoxy (or 2′-O-allyl)-ψ-isocytidine, 1,3-Dimethyl-2′-deoxy-ψ-uridine and N1-Methyl-2′-O-allyl-ψ-uridine as Synthons Suitable for Oligonucleotide Synthesis." ChemInform 26, № 2 (2010): no. http://dx.doi.org/10.1002/chin.199502221.

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25

Struhatska, Mariia B., Vladimir A. Ovchynnikov, Nataliia S. Kariaka, Paula Gawryszewska, and Volodymyr M. Amirkhanov. "Crystal structure of tetraphenyl phosphate tetrakis[dimethyl (2,2,2-trichloroacetyl)phosphoramidato]lutetium(III), PPh₄[LuL ₄]." Acta Crystallographica Section E Crystallographic Communications 80, no. 4 (2024). http://dx.doi.org/10.1107/s205698902400210x.

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A lutetium(III) complex based on the anion of the ligand dimethyl (2,2,2-trichloroacetyl)phosphoramidate (HL) and tetraphenylphosphonium, of composition PPh4[LuL 4] (L = CAPh = carbacylamidophosphate), or (C24H20)[Lu(C4H6Cl3NO4P)4], has been synthesized and structurally characterized. The X-ray diffraction study of the compound revealed that the lutetium ion is surrounded by four bis-chelating CAPh ligands, forming the complex anion [LuL 4]− with a coordination number of 8[O] for LuIII, while PPh4 + serves as a counter-ion. The coordination geometry around the Lu3+ ion was determined to be a n

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26

REWCASTLE, G. W., G. J. ATWELL, B. C. BAGULEY, and W. A. DENNY. "ChemInform Abstract: POTENTIAL ANTITUMOR AGENTS. 42. STRUCTURE-ACTIVITY RELATIONSHIPS FOR ACRIDINE-SUBSTITUTED DIMETHYL PHOSPHORAMIDATE DERIVATIVES OF 9-ANILINOACRIDINE." Chemischer Informationsdienst 16, no. 3 (1985). http://dx.doi.org/10.1002/chin.198503228.

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27

Gavrilov, K. N., I. V. Chuchelkin, V. M. Trunina, et al. "P,S-Bidentate Phosphoramidites with (Ra)-BINOL Core in Palladium-Catalyzed Asymmetric Allylic Substitution." Russian Journal of General Chemistry, December 22, 2022. http://dx.doi.org/10.1134/s1070363222120088.

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Abstract New P,S-bidentate phosphoramidite ligands, including these having a stereogenic phosphorus atom in the 1,3,2-dioxaphosphepine ring, have been synthesized on the basis of (Ra)-BINOL and its adamantanyl derivatives. With their participation in the Pd-catalyzed asymmetric allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate and the amination with pyrrolidine involving these ligands have afforded selectivity up to 84 and 75% ee, respectively.

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28

Kurihara, Kazunori, Yasunori Yamamoto та Norio Miyaura. "ChemInform Abstract: A Chiral Bidentate Phosphoramidite (Me-BIPAM) for Rh-Catalyzed Asymmetric Hydrogenation of α-Dehydroamino Esters, Enamides, and Dimethyl Itaconate." ChemInform 40, № 41 (2009). http://dx.doi.org/10.1002/chin.200941023.

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