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[ CAS No. 35333-26-7 ] {[proInfo.proName]}

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Chemical Structure| 35333-26-7
Chemical Structure| 35333-26-7
Structure of 35333-26-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 35333-26-7 ]

CAS No. :35333-26-7 MDL No. :MFCD00672057
Formula : C11H11BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :YWKKQTFYOQBCBE-UHFFFAOYSA-N
M.W : 271.11 Pubchem ID :13311991
Synonyms :

Calculated chemistry of [ 35333-26-7 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 60.53
TPSA : 54.37 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.35
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 2.3
Log Po/w (SILICOS-IT) : 2.85
Consensus Log Po/w : 2.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.292 mg/ml ; 0.00108 mol/l
Class : Soluble
Log S (Ali) : -3.13
Solubility : 0.2 mg/ml ; 0.000739 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.79
Solubility : 0.0444 mg/ml ; 0.000164 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.55

Safety of [ 35333-26-7 ]

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 [ 35333-26-7 ]

* 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 [ 35333-26-7 ]
  • Downstream synthetic route of [ 35333-26-7 ]

[ 35333-26-7 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 108-55-4 ]
  • [ 108-86-1 ]
  • [ 35333-26-7 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With aluminum (III) chloride In dichloromethane at 7℃; for 0.5 h;
Stage #2: at 20℃; for 19 h;
A flask was charged with AlCl3 (78.8 mmol, 10.5 g, 2.3 equiv) and dry CH2Cl2 (25 ml) under calcium chloride guard tube and the formed suspension was stirred on ice bath. Subsequently, a solution of glutaric anhydride 10 (34.3 mmol, 3.91 g) in dry CH2Cl2 (15 ml) was added dropwise (t < 7 °C). The resulting mixture was stirred on ice bath for 30 minutes and bromobenzene 11b (34.3 mmol, 5.39 g, 1.0 equiv) was carefully added afterwards. The cooling bath was removed and the mixture was stirred at room temperature for 19 hours, then it was poured into ice water (15 ml), acidified with conc. H2SO4 (10 ml), the aqueous layer was extracted with ethyl acetate (1 x 100 ml, 2 x 50 ml), the combined organics were dried over Na2SO4, filtered and concentrated. The crude product was dissolved in ethyl acetate and the resulting solution was added dropwise to a vigorously stirred cold hexanes (1 L). The precipitate was filtered off and dried to provide 5-(4-bromophenyl)-5-oxopentanoic acid (7.93 g, 85percent) as a yellow powder;2 mp 125-127 °C; 1H NMR (300 MHz, CDCl3): δ = 2.07 (m, 2H), 2.50 (t, J = 7.2 Hz, 2H), 3.04 (t, J = 7.2 Hz, 2H), 7.60 (m, 2H), 7.82 (m, 2H). 5-(4-Bromophenyl)-5-oxopentanoic acid (25.0 mmol, 6.78 g), paraformaldehyde (86.3 mmol, 2.59 g, 3.4 equiv) and piperidine (0.57 ml, 0.24 equiv) were dissolved/suspended in pyridine (42 ml) and stirred at 70 °C for 21 hours. Afterwards, the mixture was poured into 1M H2SO4 (200 ml)/conc. H2SO4 (15 ml), the aqueous layer was extracted with ethyl acetate (1 x 150 ml, 2 x 100 ml), the combined organics were washed with half-saturated brine (300 ml), dried over Na2SO4, filtered and concentrated. The crude product was crystallized from ethyl acetate to yield 4-(4-bromobenzoyl)pent-4-enoic acid 9b (3.93 g, 56percent) as an orange-yellow solid; mp 127-128 °C; 1H NMR (300 MHz, CDCl3): δ = 2.63 (t, J = 6.9 Hz, 2H), 2.80 (t, J = 6.9 Hz, 2H), 5.67 (s, 1H), 5.95 (s, 1H), 7.60 (m, 4H); 13C NMR (75 MHz, CDCl3): δ = 27.2, 32.6, 127.3, 127.4, 131.0, 131.6, 136.3, 145.8, 178.9, 196.6.
Reference: [1] Russian Journal of General Chemistry, 2014, vol. 84, # 9, p. 1825 - 1829[2] Zhurnal Obshchei Khimii, 2014, vol. 84, # 9, p. 1825 - 1829,5
[3] Tetrahedron Letters, 2016, vol. 57, # 10, p. 1079 - 1082
[4] Heterocycles, 2005, vol. 65, # 3, p. 649 - 656
  • 2
  • [ 898792-67-1 ]
  • [ 35333-26-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 10, p. 2049 - 2063
[2] Patent: WO2009/39553, 2009, A1, . Location in patent: Page/Page column 94-95
[3] Patent: US2012/46467, 2012, A1, . Location in patent: Page/Page column 24
  • 3
  • [ 90991-23-4 ]
  • [ 35333-26-7 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 37, p. 12871 - 12875
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 1, p. 177 - 186
  • 4
  • [ 5205-39-0 ]
  • [ 35333-26-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 10, p. 2049 - 2063
  • 5
  • [ 1501-26-4 ]
  • [ 35333-26-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 1, p. 177 - 186
[2] Chemistry - A European Journal, 2015, vol. 21, # 37, p. 12871 - 12875
  • 6
  • [ 108-86-1 ]
  • [ 35333-26-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 1, p. 177 - 186
  • 7
  • [ 1501-27-5 ]
  • [ 35333-26-7 ]
Reference: [1] Chemistry - A European Journal, 2015, vol. 21, # 37, p. 12871 - 12875
  • 8
  • [ 5205-39-0 ]
  • [ 108-86-1 ]
  • [ 35333-26-7 ]
Reference: [1] Patent: US2012/46467, 2012, A1,
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