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[ CAS No. 184429-84-3 ] {[proInfo.proName]}

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Chemical Structure| 184429-84-3
Chemical Structure| 184429-84-3
Structure of 184429-84-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 184429-84-3 ]

CAS No. :184429-84-3 MDL No. :MFCD24466259
Formula : C14H29NO4Si Boiling Point : -
Linear Structure Formula :- InChI Key :GPCWVDDNSMMEGI-UHFFFAOYSA-N
M.W : 303.47 Pubchem ID :11709260
Synonyms :

Calculated chemistry of [ 184429-84-3 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.86
Num. rotatable bonds : 9
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 83.08
TPSA : 64.63 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) : -5.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.48
Log Po/w (XLOGP3) : 3.35
Log Po/w (WLOGP) : 3.1
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 0.93
Consensus Log Po/w : 2.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.24
Solubility : 0.175 mg/ml ; 0.000578 mol/l
Class : Soluble
Log S (Ali) : -4.38
Solubility : 0.0125 mg/ml ; 0.0000412 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.41
Solubility : 0.119 mg/ml ; 0.000392 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.93

Safety of [ 184429-84-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 184429-84-3 ]

* 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 [ 184429-84-3 ]
  • Downstream synthetic route of [ 184429-84-3 ]

[ 184429-84-3 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 195197-94-5 ]
  • [ 184429-84-3 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With oxalyl dichloride; dimethyl sulfoxide In dichloromethane for 1.33333 h; Inert atmosphere; Cooling with ice
Stage #2: With triethylamine In dichloromethane at 20℃; Inert atmosphere
To a stirring solution of oxalyl chloride (13.6 mL, 0.16 mol) in dry CH2Cl2 (150 mL) at -78°C under N2 was added DMSO (15.2 mL, 0.21 mol) dropwise over 30 min. After complete addition the resulting solution was stirred at -78°C for 1 h. A solution of tert-butyl 3-(rt-butyldimethyl-silyloxy)-2-hydroxypropylcarbamate (32.6 g, 0.1 1 mol) in CH2Cl2 (50 mL) was then added dropwise over 20 min. Stirring was continued for a further 1 hour at which time triethylamine (59.6 mL, 0.43 mol) was added. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The reaction mixture was partitioned between water (100 mL) and CH2Cl2 (70 mL) and the aqueous layer was extracted with further CH2Cl2 (2 x 70 mL); the combined organics were dried over Na2SO4 and concentrated under a stream of nitrogen gas. The crude residue was purified over silica gel eluting with 5percent ethylacetate in n-hexane to give tert- butyl 3-(tert-butyldimethylsilyloxy)-2-oxopropylcarbamate (29.8 g, 92percent) as a pale yellow oil. 1H-NMR (300 MHz; CDCl3) ppm: 0.11 (6 H, s), 0.94 (9 H, s), 1.47 (9 H, s), 3.92 (2 H, s), 4.26 (2 H, d, J4.6 Hz), 5.22 (1 H, br s).
Reference: [1] Patent: WO2013/163675, 2013, A1, . Location in patent: Paragraph 00182
[2] Canadian Journal of Chemistry, 1997, vol. 75, # 7, p. 942 - 948
[3] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1191 - 1197
[4] Journal of Pharmacology and Experimental Therapeutics, 2013, vol. 347, # 2, p. 365 - 374
  • 2
  • [ 24424-99-5 ]
  • [ 184429-84-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1191 - 1197
[2] Canadian Journal of Chemistry, 1997, vol. 75, # 7, p. 942 - 948
[3] Patent: WO2013/163675, 2013, A1,
  • 3
  • [ 137618-48-5 ]
  • [ 184429-84-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1191 - 1197
[2] Canadian Journal of Chemistry, 1997, vol. 75, # 7, p. 942 - 948
[3] Patent: WO2013/163675, 2013, A1,
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