Home Cart 0 Sign in  
X

[ CAS No. 126430-46-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 126430-46-4
Chemical Structure| 126430-46-4
Chemical Structure| 126430-46-4
Structure of 126430-46-4 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 126430-46-4 ]

Related Doc. of [ 126430-46-4 ]

Alternatived Products of [ 126430-46-4 ]

Product Details of [ 126430-46-4 ]

CAS No. :126430-46-4 MDL No. :MFCD00143681
Formula : C11H13BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JJUJDJNFXYNOKI-UHFFFAOYSA-N
M.W : 257.12 Pubchem ID :3832489
Synonyms :

Calculated chemistry of [ 126430-46-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 6
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 59.79
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 3.05
Log Po/w (WLOGP) : 2.75
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 3.3
Consensus Log Po/w : 2.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.28
Solubility : 0.136 mg/ml ; 0.000529 mol/l
Class : Soluble
Log S (Ali) : -3.27
Solubility : 0.139 mg/ml ; 0.000539 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.56
Solubility : 0.00707 mg/ml ; 0.0000275 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.94

Safety of [ 126430-46-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P305+P351+P338-P312-P337+P313 UN#:N/A
Hazard Statements:H302-H312-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 126430-46-4 ]

* 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 [ 126430-46-4 ]
  • Downstream synthetic route of [ 126430-46-4 ]

[ 126430-46-4 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 927-58-2 ]
  • [ 100-51-6 ]
  • [ 126430-46-4 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In dichloromethane for 2 h; To a solution of 4-bromobutyryl chloride (Aldrich Chemical Company, Wisconsin), (10.27 g, 55.4 mmol) in 100 mL of dichloromethane was added benzyl alcohol (Aldrich Chemical Company, Wisconsin), (6.29 g, 58.1 mmol), followed by potassium carbonate (8.3 g, 60 mmol) in four portions. After 2 hours, water was added, and the layers were separated. The organic layer was washed with water, brine, and dried over magnesium sulfate. Evaporation of the solvent gave the title compound (11.87 g, 83percent yield) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.36 (m, 5H), 5.14 (s, 2H), 3.46 (t, J=6.4 Hz, 2H), 2.56 (t, J=7.2 Hz, 2H), 2.20 (quin, J=6.6 Hz, 2H).
82% With dmap In dichloromethane at 20℃; for 2 h; [00140] Benzyl alcohol (3.1 ml_, 30 mmol) was added to a solution of Compound 1 (3.47 ml_, 30 mmol) and 4-dimethylaminopyridine (732 mg, 6 mmol) in dichloromethane (100 ml_). The reaction was stirred for 2 hours at room temperature then quenched with 1 M HCI (100 ml_). The organic phase was washed once more with 1 M HCI (100 ml_), dried over MgS04, filtered, dried by rotary evaporation and was dried under vacuum to yield Compound 2 as a colorless oil (6.29 g, 24.5 mmol, 82percent).
Reference: [1] Patent: US2006/189603, 2006, A1, . Location in patent: Page/Page column 57
[2] Patent: WO2016/86026, 2016, A1, . Location in patent: Paragraph 00140
[3] Journal of Medicinal Chemistry, 1996, vol. 39, # 26, p. 5176 - 5182
[4] Synthesis, 2010, # 6, p. 953 - 958
[5] Patent: EP1724278, 2006, A1, . Location in patent: Page/Page column 44-45
  • 2
  • [ 2623-87-2 ]
  • [ 100-51-6 ]
  • [ 126430-46-4 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With S-phenyl benzenethiosulfinate; diisopropyl-carbodiimide In dichloromethane at 20℃; for 2 h;
General procedure: General Procedure for Benzyl Protection of the Bromo-Acid (1c, 1d) [0103] Diisopropylcarbodiimide (DIC) (3.59 mmol, 1.3 eq) was added to a mixture of the bromo-acid (4-bromobutyric acid or 5-bromovaleric acid) (2.76 mmol, 1 eq) and DPTS (3.04 mmol, 1.1 eq) in dry DCM (30 mL) and was allowed to react for 2 hours at room temperature. Benzyl alcohol (4.14 mmol, 1.5 eq) was added and allowed to react overnight. The reaction was washed water and brine, and the DCM was removed by evaporation. Hexanes was added and the resulting white precipitate was removed by filtration. The hexanes was removed from the filtrate by evaporation resulting in an oil which was purified by silica gel chromatography (Hexanes/Ethyl Acetate 3.5/1). Benzyl 4-bromobutyrate (1c) [0104] 70percent yield [0105] 1H NMR (500 MHz, CDCl3) 2.22 (p 2H), 2.58 (t, 2H), 3.48 (t, 2H), 5.16 (s, 2H), 7.40 (m, 5H) [0106] 13C NMR (125 MHz, CDCl3): 28.0, 32.7, 33.0, 66.7, 128.5, 128.6, 128.9, 136.1, 172.6
Reference: [1] European Journal of Organic Chemistry, 2008, # 15, p. 2592 - 2600
[2] Advanced Synthesis and Catalysis, 2007, vol. 349, # 3, p. 432 - 440
[3] Journal of Organic Chemistry, 2001, vol. 66, # 12, p. 4115 - 4121
[4] Journal of the American Chemical Society, 2011, vol. 133, # 41, p. 16346 - 16349
[5] Patent: US2013/302258, 2013, A1, . Location in patent: Paragraph 0102; 0103; 0104; 0105; 0106
[6] Chemistry - A European Journal, 2016, vol. 22, # 4, p. 1270 - 1276
[7] Patent: EP1544208, 2005, A1, . Location in patent: Page/Page column 58
  • 3
  • [ 2623-87-2 ]
  • [ 501-53-1 ]
  • [ 126430-46-4 ]
Reference: [1] MedChemComm, 2015, vol. 6, # 3, p. 403 - 406
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 126430-46-4 ]

Aryls

Chemical Structure| 103-40-2

[ 103-40-2 ]

4-(Benzyloxy)-4-oxobutanoic acid

Similarity: 0.88

Chemical Structure| 3089-55-2

[ 3089-55-2 ]

Benzyl octyl adipate

Similarity: 0.86

Chemical Structure| 54322-10-0

[ 54322-10-0 ]

5-(Benzyloxy)-5-oxopentanoic acid

Similarity: 0.86

Chemical Structure| 122-63-4

[ 122-63-4 ]

Benzyl propionate

Similarity: 0.83

Chemical Structure| 5437-45-6

[ 5437-45-6 ]

Benzyl 2-bromoacetate

Similarity: 0.82

Bromides

Chemical Structure| 5437-45-6

[ 5437-45-6 ]

Benzyl 2-bromoacetate

Similarity: 0.82

Chemical Structure| 25109-86-8

[ 25109-86-8 ]

Methyl 2-(2-bromoethyl)benzoate

Similarity: 0.80

Chemical Structure| 113100-86-0

[ 113100-86-0 ]

Methyl 4-(3-bromopropyl)benzoate

Similarity: 0.78

Chemical Structure| 136333-97-6

[ 136333-97-6 ]

Methyl 4-(2-bromoethyl)benzoate

Similarity: 0.78

Chemical Structure| 1129-28-8

[ 1129-28-8 ]

Methyl 3-(bromomethyl)benzoate

Similarity: 0.74

Esters

Chemical Structure| 103-40-2

[ 103-40-2 ]

4-(Benzyloxy)-4-oxobutanoic acid

Similarity: 0.88

Chemical Structure| 3089-55-2

[ 3089-55-2 ]

Benzyl octyl adipate

Similarity: 0.86

Chemical Structure| 54322-10-0

[ 54322-10-0 ]

5-(Benzyloxy)-5-oxopentanoic acid

Similarity: 0.86

Chemical Structure| 122-63-4

[ 122-63-4 ]

Benzyl propionate

Similarity: 0.83

Chemical Structure| 5437-45-6

[ 5437-45-6 ]

Benzyl 2-bromoacetate

Similarity: 0.82