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[ CAS No. 5927-18-4 ] {[proInfo.proName]}

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Chemical Structure| 5927-18-4
Chemical Structure| 5927-18-4
Structure of 5927-18-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 5927-18-4 ]

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Product Details of [ 5927-18-4 ]

CAS No. :5927-18-4 MDL No. :MFCD00008452
Formula : C5H11O5P Boiling Point : -
Linear Structure Formula :(CH3O)2P(O)CH2CO2CH3 InChI Key :SIGOIUCRXKUEIG-UHFFFAOYSA-N
M.W : 182.11 Pubchem ID :80029
Synonyms :
Chemical Name :Methyl 2-(dimethoxyphosphoryl)acetate

Calculated chemistry of [ 5927-18-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.27
TPSA : 71.64 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : -0.61
Log Po/w (WLOGP) : 0.65
Log Po/w (MLOGP) : -0.55
Log Po/w (SILICOS-IT) : -0.57
Consensus Log Po/w : 0.11

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.25
Solubility : 101.0 mg/ml ; 0.556 mol/l
Class : Very soluble
Log S (Ali) : -0.42
Solubility : 68.8 mg/ml ; 0.378 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.63
Solubility : 42.3 mg/ml ; 0.232 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.37

Safety of [ 5927-18-4 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P362+P364-P403+P233-P501 UN#:3082
Hazard Statements:H302-H315-H318-H335-H411 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 5927-18-4 ]

* 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 [ 5927-18-4 ]

[ 5927-18-4 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 5927-18-4 ]
  • [ 5077-67-8 ]
  • [ 1575-44-6 ]
  • 2
  • [ 5927-18-4 ]
  • [ 51716-63-3 ]
  • 7-((methoxycarbonyl)methylene)-cis-bicyclo<3.3.0>octan-3-one [ No CAS ]
  • 3
  • [ 870837-70-0 ]
  • [ 5927-18-4 ]
  • (E)-3-[4-(1H-imidazol-1-yl)-3-methoxyphenyl)acrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Dimethylphosphonoacetic acid methyl ester (3.80 mL) and lithium hydroxide monohydrate (1.20 g) were added one by one to a THF (20 mL) solution of the crude aldehyde compound (4.76 g) obtained above, and the reaction solution was agitated overnight at the room temperature. 2N sodium hydroxide solution was added to the reaction solution after confirming disappearance of the starting materials (20 mL), and the reaction solution was agitated at 50 C. for 2 hours. The reaction solution was cooled to 0 C., 2N hydrochloric acid was added to the reaction solution (20 mL), and deposited precipitation was separated by filtering with Kiriyama funnel. The obtained precipitation was washed with water and ethyl acetate, and 4.2 g of the title compound was obtained. The physical properties of the compound are as follows. 1H-NMR (DMSO-d6) delta (ppm): 7.96 (s, 1H), 7.63 (d, J=16 Hz, 1H), 7.60 (d, J=1.6 Hz, 1H), 7.48 (s, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.39 (dd, J=1.6, 8.0 Hz, 1H), 7.06 (s, 1H), 6.68 (d, J=16 Hz, 1H), 3.90 (s, 3H).
  • 4
  • [ 5927-18-4 ]
  • [ 17429-02-6 ]
  • [ 1108195-95-4 ]
YieldReaction ConditionsOperation in experiment
69% (4-Methoxy-4 methyl-cyclohexylidene)-acetic acid methyl ester A mixture of trimethyl phosphonoacetate (9.11 mL, 56 mmol) and (40 mL, 64 mmol) of n-BuLi (1.6N) in DME (60 mL) is stirred for 10 minutes at 0 C. <strong>[17429-02-6]4-Hydroxy-4-methyl-cyclohexanon</strong>e (8 g, 56 mmol) was added and the mixture stirred 2.5 hours at 0 C. until TCL indicated complexion of the reaction. Product was obtained after extraction with dichloromethane (7.71 g, 69%).
  • 5
  • [ 5927-18-4 ]
  • [ 865-47-4 ]
  • [ 62327-21-3 ]
YieldReaction ConditionsOperation in experiment
In 2-MeTHF; at 5 - 20℃; Intermediate 64-8: Methyl 2-fn r.4rWU4-f4A5.5-tetramethyl-T .3.2-rtioxahorolan-2- vDnhenylkvclohexyDacetateTrimethylphosphonoacetate (1.05X-1.06X) was added dropwise to a suspended solution of t-BuOK (0.70X-0.71X) in 2-MeTHF (10 vol) at 5-1O0C. The resulting solution was stirred at 15-2O0C for 3.5-4.0 hours. The reaction mixture was cooled to 5-1O0C and DIPEA (0.81-0.82X) was added to the reaction at 10-150C. 4-(4-Hydroxyphenyl)cyclohexanone (1.0 X) was added in portions to the above reaction mixture at 10-150C and the resulting solution was stirred at 15-2O0C for 3-6 hours and then sampled for HPLC analysis. NH4C1- sol (5.0X-6.0X) was added to the reaction mixture at 0-150C, and the reaction was quenched. The organic layer was separated and the aqueous layer was extracted with 2- MeTHF (2.5X-3.0X). The two organic extracts were combined and washed with NaHSO3 aq. and then NaCl-solution (2.5X-3.0X) twice. The organic layer was concentrated to 2~3 vol and n-heptane was added to give a suspended solution, and the above mixture was <n="163"/>concentrated to below 3percent of 2-MeTHF residue to give a suspended solution. The mixture was cooled to 0-5 0C, stirred for 1.0-2.0 h, filtered and the cake washed with n-heptane (2 vol X2). Dry in vacuum at below 450C to give the desired phenoxyacrylate product.
  • 6
  • [ 5927-18-4 ]
  • [ 14615-72-6 ]
  • [ 64793-98-2 ]
  • 7
  • [ 5927-18-4 ]
  • [ 156866-52-3 ]
  • 3-[4-(tert-butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% To a solution of trimethyl phosphino acetate (4.64 mL, 23.5 mmol) in dry DMF (20 mL) was added potassium tert-butoxide (2.14 g, 19.13 mmol) at 0° C. and the mixture was stirred at same temperature over a period of 15 min.To the above mixture a solution of <strong>[156866-52-3](4-Formyl-benzyl)-carbamic acid tert-butyl ester</strong> (3.0 g, 12.75 mmol) in DMF (10 mL) was added drop wise at ice temperature.The reaction mixture was stirred at ice temperature over a period of 45 min.The resulting reaction mixture diluted with ethyl acetate, washed with water, brine and dried over sodium sulfate.The residue obtained upon evaporation of volatiles was purified by column chromatography to give 3-[4-(tert-Butoxycarbonylamino-methyl)-phenyl]-acrylic acid methyl ester as colourless solid (1.5 g, 40percent).
  • 8
  • [ 5927-18-4 ]
  • [ 35344-95-7 ]
  • [ 1295583-21-9 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In 1,4-dioxane; dimethyl sulfoxide; at 20 - 100℃; (E)-methyl 3-(l -methyl- lH-pyrazol-4-yl)acrylateCs2C03 (1.304g, 4 mmol) was added to a solution of lH-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong> (0.192 g, 2 mmol) in dioxane (8 mL) at room temperature. Trimethylphosphonoacetate (0.364g, 0.40 mmol) was added to this suspension, followed by DMSO (2 mL). The reaction mixture was heated to 100°C overnight. It was then diluted with EtOAc (40 mL), and washed with water (40 mL) and brine (20 mL). The organic layer was concentrated under vacuum. The crude was purified by silica gel column chromatography using a 0-100percent gradient of EtOAc in hexanes to provide (E)-methyl 3 -(1 -methyl- lH-pyrazol-4- yl)acrylate (0.278 g). ES+ (M+H)+ 167
0.278 g With caesium carbonate; In 1,4-dioxane; dimethyl sulfoxide; at 20 - 100℃; Cs2CO3 (1.304 g, 4 mmol) was added to a solution of <strong>[35344-95-7]1H-<strong>[35344-95-7]pyrazole-4-carbaldehyde</strong></strong> (0.192 g, 2 mmol) in dioxane (8 mL) at room temperature. Trimethylphosphonoacetate (0.364 g, 0.40 mmol) was added to this suspension, followed by DMSO (2 mL). The reaction mixture was heated to 100° C. overnight. It was then diluted with EtOAc (40 mL), and washed with water (40 mL) and brine (20 mL). The organic layer was concentrated under vacuum. The crude was purified by silica gel column chromatography using a 0-100percent gradient of EtOAc in hexanes to provide (E)-methyl 3-(1-methyl-1H-pyrazol-4-yl)acrylate (0.278 g). ES+(M+H)+167
  • 9
  • [ 790667-49-1 ]
  • [ 5927-18-4 ]
  • [ 1338821-09-2 ]
YieldReaction ConditionsOperation in experiment
Step 2. Synthesis of tert-butyl (2S,4E)- and tert-butyl (2S,4Z)-4-(2-methoxy-2-oxoethylidene)-2-methylpiperidine-1-carboxylate (C20) Sodium hydride (60% in mineral oil, 1.35 g, 33.6 mmol) was washed with hexanes (2*5 mL), suspended in N,N-dimethylformamide (40 mL) and cooled to 0 C. Methyl (dimethoxyphosphoryl)acetate (4.66 mL, 32.3 mmol) was added to the reaction in a drop-wise manner, and the mixture was held at 0 C. with vigorous stirring for 20 minutes. A solution of <strong>[790667-49-1]ter<strong>[790667-49-1]t-butyl (2S)-2-methyl-4-oxopiperidine-1-carboxylate</strong></strong> (C19) (5.52 g from the previous experiment, ?24.3 mmol) in N,N-dimethylformamide (10 mL) was added drop-wise, and the resulting solution was allowed to warm to room temperature over 16 hours. The reaction was then diluted with diethyl ether (400 mL) and washed with water (300 mL). The aqueous layer was extracted with diethyl ether (200 mL) and the combined organic layers were washed with water (4*200 mL) and saturated aqueous sodium chloride solution (200 mL), then dried over magnesium sulfate, filtered and concentrated under reduced pressure. The product was obtained as a colorless oil, composed of a roughly 1:1 mixture of olefin isomers. Yield: 6.63 g, 24.6 mmol, quantitative. 1H NMR (400 MHz, CDCl3) delta 5.83 and 5.72 (2 br s, 1H), 4.44-4.61 (m, 1H), 3.98-4.14 (m, 1H), 3.71 and 3.70 (2 s, 3H), 3.58-3.70 (m, 1H), 2.93-3.03 (m, 1H), 2.06-2.11, 2.18-2.33 and 2.53-2.59 (multiplets, total 3H), 1.47 (2 s, 9H), 1.08 (d, J=6.7 Hz) and 1.07 (d, J=6.9 Hz, total 3H).
  • 10
  • [ 5927-18-4 ]
  • [ 24078-12-4 ]
  • methyl (E)-3-(4-bromo-2-methylphenyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; at 20℃; for 19h; To a mixture of <strong>[24078-12-4]4-bromo-2-methylbenzaldehyde</strong> (5.87 mL, 44 mmol, 1 equiv.) and trimethyl phosphonoacetate (7.62 mL, 53 mL, 1.2 equiv.) was added potassium carbonate (12.1 g, 88 mmol, 2 equiv.) and DBU (0.2 mL, 1.3 mmol, 0.03 equiv.). The reaction was stirred at room temperature for 19 h before being quenched with water. It was extracted three times with ether, the combined organic extracts were dried over sodium sulfate and the solvent was evaporated. The residue was purified by bulb-to-bulb distillation (135-140C, 0.15 mbar) to afford methyl (E)-3-(4-bromo-2-methylphenyl)acrylate (10.3 g, 92 % yield).1H NMR: 2.40 (s, 3H), 3.81 (s, 3H), 6.34 (d, / = 15.9, 1H), 7.32.7.40 (m, 3H), 7.87 (d, / =15.9, 1H). 13C NMR: 167.2 (s), 141.3 (d), 139.6 (s), 133.6 (d), 132.4 (s), 129.6 (d), 127.8 (d), 124.1 (s), 119.5 (d), 51.8 (q), 19.6 (q).
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[ 5927-18-4 ]

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Chemical Structure| 163487-10-3

[ 163487-10-3 ]

Methyl (E)-3-(3-aminophenyl)acrylate

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