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[ CAS No. 4408-64-4 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 4408-64-4
Chemical Structure| 4408-64-4
Structure of 4408-64-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 4408-64-4 ]

CAS No. :4408-64-4 MDL No. :MFCD00004284
Formula : C5H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :XWSGEVNYFYKXCP-UHFFFAOYSA-N
M.W : 147.13 Pubchem ID :20441
Synonyms :

Calculated chemistry of [ 4408-64-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.6
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 32.59
TPSA : 77.84 Ų

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) : -9.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.79
Log Po/w (XLOGP3) : -3.32
Log Po/w (WLOGP) : -0.91
Log Po/w (MLOGP) : -0.96
Log Po/w (SILICOS-IT) : -1.39
Consensus Log Po/w : -1.16

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : 1.6
Solubility : 5900.0 mg/ml ; 40.1 mol/l
Class : Highly soluble
Log S (Ali) : 2.26
Solubility : 26700.0 mg/ml ; 182.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 0.86
Solubility : 1070.0 mg/ml ; 7.24 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.3

Safety of [ 4408-64-4 ]

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 [ 4408-64-4 ]

* 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.

  • Upstream synthesis route of [ 4408-64-4 ]
  • Downstream synthetic route of [ 4408-64-4 ]

[ 4408-64-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 4408-64-4 ]
  • [ 1826-67-1 ]
  • [ 1104636-73-8 ]
YieldReaction ConditionsOperation in experiment
55%
Stage #1: With Trimethyl borate In tetrahydrofuran at -78 - 23℃; for 5.5 h; Inert atmosphere
Stage #2: at 105 - 115℃; for 2.16667 h; Inert atmosphere
To a 3 L three-neck round bottom flask equipped with a stir bar were added B(OMe)3 (94 mL, 840 mmol) and THF (600 mL). The solution was cooled to 78 °C. Vinylmagnesium bromide (1.0 M in THF, 800 mL, 800 mmol) was added dropwise via cannula over 2 h 45 min. The resulting solution was stirred at 78 °C for 15 min, followed by stirring at 23 °C for 2 h 30 min. In a separate 2 L three neckround bottom flask equipped with a stir bar, internal thermometer, and distillation apparatus were added dry MIDA (235.0 g, 1.6 mol) and DMSO (600 mL). The solution was heated with an oil bath to an internal temperature of 110-115 °C. The borate suspension was added dropwise to the hot MIDA solution via a Teflon cannula dropwise over 2 h 10 min, keeping the internal temperature between 105 and 115 °C. After full addition of the borate solution, the reaction solution was cooled to 23 °C. The resulting solution was transferred to a separatory funnel containing H2O (1 L), brine (1 L), EtOAc (1.5 L), and acetone (1 L). The mixture was shaken and the aqueous layer was removed and extracted with EtOAc/acetone (2:1, 2600 mL). The combined organic layers were washed with H2O (2500 mL). The combined water washes were back extracted with EtOAc/acetone (2:1, 2300 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo. The resulting solid was suspended in 300 mL acetone and 4 L Et2O was added to precipitate the product. The resulting solid was collected by vacuum filtration to yield vinyl MIDA boronate 1 as a white solid (81.2 g, 55percent). Spectral data for 1 were consistent with those previously reported from our laboratories.13
Reference: [1] Tetrahedron, 2013, vol. 69, # 36, p. 7732 - 7740
  • 2
  • [ 4408-64-4 ]
  • [ 1104636-73-8 ]
YieldReaction ConditionsOperation in experiment
54% at 95 - 115℃; Example 4Preparation of Vinyl MIDA Boronate from Corresponding Grignard ReagentTo a dry 500 mL Schlenk flask equipped with a stir bar was added THF (100 mL) and B(OMe)3 (11.7 mL, 105 mmol). The solution was cooled via a -78° C. cold bath. To the solution was added via cannula over 5 min. vinylmagnesium bromide as a solution in THF (1.0 M, 100 mL, 100 mmol). The resulting mixture was stirred for 2 h, then the cold bath was removed and the mixture was allowed to warm to room temperature with stirring for 2 h. The beige mixture was transferred to a 250 mL pressure-equalizing addition funnel. A 3-neck 500 mL round bottom flask equipped with a stir bar was charged with DMSO (100 mL), N-methyliminodiacetic acid (29.5 g, 200 mmol) and toluene (50 mL). To the necks of the round bottom were fitted the addition funnel, a thermometer, and a std. distillation apparatus. The mixture was heated to an internal temperature of 115° C. upon which the THF mixture was added via the addition funnel at a rate to maintain an internal temperature between 95-110° C. During this time the THF is distilled away from the hot DMSO mixture. Upon completion of the addition and after the internal temperature had risen to 120° C. the distillation pot was allowed to cool to room temperature.The DMSO mixture was diluted with acetone (300 mL) and the resulting mixture was filtered through a pad of Celite. The collected solids were extracted with acetone (100 mL) and the combined filtrate was concentrated in vacuo to afford a DMSO solution. The DMSO solution was distilled to near dryness (1 Torr, 100° C.). The remaining solids were dissolved in acetone:water (100 mL:100 mL) and were transferred to a 1000 mL separatory funnel. The solution was diluted with brine (100 mL) and EtOAc (200 mL). The mixture was shaken and the phases were separated. The aq. phase was twice extracted with acetone:EtOAc (100 mL:200 mL). The combined organics were washed with brine (3.x.100 mL). The combined brine washes were back-extracted with EtOAc (100 mL). The combined organics were dried over MgSO4, filtered, then concentrated in vacuo to afford an off-white solid which was then recrystallized from acetone (100 mL) diluted with Et2O (2000 mL) to afford the product 7c as an off-white solid (9.95 g, 54percent).
Reference: [1] Patent: US2011/201806, 2011, A1, . Location in patent: Page/Page column 15
  • 3
  • [ 4408-64-4 ]
  • [ 10294-33-4 ]
  • [ 754-05-2 ]
  • [ 1104636-73-8 ]
YieldReaction ConditionsOperation in experiment
48%
Stage #1: at 20℃; for 13 h;
Stage #2: at 23℃; for 0.0833333 h;
Vinyl-MIDA-Boronate (306); To a dry 6 mL vial fitted with a septum cap, equipped with a stir bar, and placed under Ar atmosphere was added BBr3 in CH2Cl2 (1.3 mL, 1.0 M, 1.3 mmol). To the stirred solution was added vinyltrimethylsilane (140 μL, 0.983 mmol). The solution was stirred at room temperature for 13 h. Separately, a dry 25 mL round bottom flask equipped with a stir bar, fitted with a rubber septum, and placed under Ar atm. was charged with sodium N-methyliminodiacetate (478 mg, 2.50 mmol) and DMSO (4 mL). To this stirred suspension was added dropwise by syringe the crude vinylboron dibromide solution. The mixture was stirred for 5 min. The mixture was concentrated in vacuo. The residue was adsorbed onto Florisil gel from an acetone suspension. The resulting powder was dry-loaded onto a silica gel column slurry packed in Et2O. The column was flushed with Et2O (app. 200 mL), then was eluted with Et2O:MeCN (3:1) to afford 306 as a colorless solid, 88 mg (48percent).
Reference: [1] Patent: US2009/30238, 2009, A1, . Location in patent: Page/Page column 23
  • 4
  • [ 4408-64-4 ]
  • [ 754-05-2 ]
  • [ 1104636-73-8 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 16, p. 3130 - 3138
  • 5
  • [ 4408-64-4 ]
  • [ 1104636-73-8 ]
Reference: [1] Journal of Organic Chemistry, 2015, vol. 80, # 11, p. 5428 - 5435
  • 6
  • [ 4363-34-2 ]
  • [ 4408-64-4 ]
  • [ 1104636-73-8 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 17, p. 5300 - 5303
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